[
  {
    "id": "counterfactual-f008",
    "app": "batbucks",
    "instruction": "What if I sold all my GameStop and Rivian and rolled the whole thing into VTI? Use cost basis (no live prices) and show me what my portfolio would look like before and after, with percentages. Use LibreOffice Calc to report this.",
    "apps_involved": [
      "BatBucks",
      "LibreOffice Calc"
    ],
    "category": "counterfactual",
    "difficulty": "medium",
    "category_v2": "cross_source_reconciliation"
  },
  {
    "id": "hard_app-f003",
    "app": "batbucks",
    "instruction": "Time to rebalance my BatBucks portfolio into something a financial advisor wouldn't laugh at. I'm aiming for roughly 60% VTI / 20% SBUX / 20% DIS across the blue-chip bucket at cost basis (RIVN stays put \u2014 I'm not touching that one). Sell every share of GME I'm holding to free up cash, then use that plus my free cash to buy enough VTI to push the allocation toward 60%. Do this as a cost-basis rebalance, not live prices. Exact percentages aren't required \u2014 a reasonable approximation toward the 60/20/20 shape is the goal.",
    "apps_involved": [
      "BatBucks"
    ],
    "category": "situated_action",
    "difficulty": "hard",
    "category_v2": "bounded_action"
  },
  {
    "id": "hard_app-f004",
    "app": "batbucks",
    "instruction": "I want downside protection on every position I'm holding in BatBucks. Put a couple Stop order on each one at 15% below what I paid for it, just to give me a floor. Then build me a new watchlist called 'Oscar's Picks' with eight big-name ETFs in it. Make sure the stop-losses actually show up in my open orders and the watchlist is still there if I refresh.",
    "apps_involved": [
      "BatBucks"
    ],
    "category": "situated_action",
    "difficulty": "hard",
    "category_v2": "bounded_action"
  },
  {
    "id": "preference_inference-f005",
    "app": "batbucks",
    "instruction": "Take a look at my brokerage portfolio. How bad is my meme-stock problem, and what would a sensible rebalance look like that doesn't totally abandon the names I actually like? Use cost basis, not market prices. While you're at it, peek at my old WUPHF investment agreement in ~/Downloads/ \u2014 that one was the OG mistake, and it sets the pattern for how I get into these things. Return the review of my portfolio in LibreOffice Writer.",
    "apps_involved": [
      "BatBucks"
    ],
    "category": "preference_inference",
    "difficulty": "medium",
    "category_v2": "pattern_inference"
  },
  {
    "id": "retrieval-f016",
    "app": "batbucks",
    "instruction": "What's my total BatBucks portfolio worth at cost basis across everything I'm holding, and how much cash is sitting in the account?",
    "apps_involved": [
      "BatBucks"
    ],
    "category": "retrieval",
    "difficulty": "medium",
    "category_v2": "personal_lookup"
  },
  {
    "id": "situated_action-f017",
    "app": "batbucks",
    "instruction": "Trim my GameStop position in half and roll the proceeds into VTI. I'm trying to be less of a degenerate about this.",
    "apps_involved": [
      "BatBucks"
    ],
    "category": "situated_action",
    "difficulty": "hard",
    "category_v2": "bounded_action"
  },
  {
    "id": "preference_inference-f014",
    "app": "cheskepdia",
    "instruction": "Look at my hotel and resort bookings on Cheskepdia. Am I a luxury-hotels guy or a budget-hotels guy, and what's my pattern?",
    "apps_involved": [
      "Cheskepdia"
    ],
    "category": "preference_inference",
    "difficulty": "medium",
    "category_v2": "pattern_inference"
  },
  {
    "id": "situated_action-f028",
    "app": "cheskepdia",
    "instruction": "I'm feeling nostalgic. Book me an upcoming Scranton weekend, Friday through Sunday. Pick a well-rated property in town and book it.",
    "apps_involved": [
      "Cheskepdia"
    ],
    "category": "situated_action",
    "difficulty": "hard",
    "category_v2": "bounded_action"
  },
  {
    "id": "cua_only-f001",
    "app": "dinoco_airlines",
    "instruction": "Open the Dinoco Airlines app, check in my next upcoming flightand confirm that the boarding pass screen actually renders. Download it locally as well.",
    "apps_involved": [
      "Dinoco Airlines"
    ],
    "category": "cua_only",
    "difficulty": "medium",
    "category_v2": "bounded_action"
  },
  {
    "id": "aggregation-f001",
    "app": "dinoco_airlines",
    "instruction": "How many miles have I actually flown on Dinoco over the past 12 months? Add up the miles from every completed Dinoco flight in that window. Give me a spreadsheet of each trip, and the miles for each one with a final row of the cumulative miles. Also include the upcoming trips and their milage.",
    "apps_involved": [
      "Dinoco Airlines"
    ],
    "category": "aggregation",
    "difficulty": "medium",
    "category_v2": "aggregation_reporting"
  },
  {
    "id": "situated_action-f001",
    "app": "dinoco_airlines",
    "instruction": "Book me a one-way Dinoco flight from AVP to JFK in Economy for next Friday with my MasterCard. Make sure you get a seat on the left and a flight in the evening or night. Can you check that the we got a confirmation email for the flight and pull it up?",
    "apps_involved": [
      "Dinoco Airlines",
      "HooliMail"
    ],
    "category": "situated_action",
    "difficulty": "hard",
    "category_v2": "bounded_action"
  },
  {
    "id": "retrieval-f001",
    "app": "dinoco_airlines",
    "instruction": "What's my current FlyMiles loyalty tier on Dinoco and how many miles do I have in the bank?",
    "apps_involved": [
      "Dinoco Airlines"
    ],
    "category": "retrieval",
    "difficulty": "easy",
    "category_v2": "personal_lookup"
  },
  {
    "id": "hard_app-f001",
    "app": "dinoco_airlines",
    "instruction": "Cancel my next flight on Dinoco. After cancelling, verify we get an email for the cancellation, and pull it up. Let me know what you cancelled and how much credit we received.",
    "apps_involved": [
      "Dinoco Airlines",
      "HooliMail"
    ],
    "category": "hard_app",
    "difficulty": "hard",
    "category_v2": "bounded_action"
  },
  {
    "id": "aggregation-f019",
    "app": "etaxi",
    "instruction": "How much have I actually spent taking eTaxi to the Dunder Mifflin office this year? Just the commute rides. Sum up and report the total cost in a LibreOffice Calc sheet.",
    "apps_involved": [
      "eTaxi"
    ],
    "category": "aggregation",
    "difficulty": "medium",
    "category_v2": "aggregation_reporting"
  },
  {
    "id": "situated_action-f038",
    "app": "etaxi",
    "instruction": "Verify my saved work/office address on my ride app is set to Dunder Mifflin at 1725 Slough Ave (Suite 200, Scranton, PA). Report back what's currently saved \u2014 if it already matches, no action needed; if it's wrong or missing, fix it and save the change.",
    "apps_involved": [
      "eTaxi"
    ],
    "category": "situated_action",
    "difficulty": "medium",
    "category_v2": "bounded_action"
  },
  {
    "id": "retrieval-f020",
    "app": "files",
    "instruction": "Where did I save my Threat Level Midnight sequel notes? Should be tucked somewhere under ~/Documents/Projects. Give me a quick rundown of what's in there (plot, cast, whatever I had going). Can you draft up a script that I can use as a starting point? Make sure you include everyone from work as a character, for casting reasons.",
    "apps_involved": [
      "Files"
    ],
    "category": "retrieval",
    "difficulty": "medium",
    "category_v2": "personal_lookup"
  },
  {
    "id": "retrieval-f032",
    "app": "files",
    "instruction": "I remember making a Dundies categorization document. Show me the Dundies 2026 categories I came up with. Where is the doc and what categories did I put down? Can you make a presentation with these categories using LibreOffice Impress so I can prepare for the Dundies? Message each of the candidates to make sure they show up to the Dundies.",
    "apps_involved": [
      "Files",
      "LibreOffice Impress",
      "HooliWork",
      "HooliMail"
    ],
    "category": "retrieval",
    "difficulty": "medium",
    "category_v2": "multi_step_orchestration"
  },
  {
    "id": "retrieval-f033",
    "app": "files",
    "instruction": "I'm working on my book, 'Somehow I Manage'. Where did I save Chapter 1, and can you give me a quick summary of what's in it? If you can write an extension for two more chapters in LibreOffice Writer, that would be great.",
    "apps_involved": [
      "Files",
      "LibreOffice Writer"
    ],
    "category": "retrieval",
    "difficulty": "hard",
    "category_v2": "personal_lookup"
  },
  {
    "id": "situated_action-f029",
    "app": "files",
    "instruction": "Open my Threat Level Midnight sequel notes file and add five new plot points for me. Big ones. Michael Scarn's back. Send out the revised plot notes to a handful of my friends from work, who could be used for casting.",
    "apps_involved": [
      "Files",
      "HooliMail",
      "HooliWork"
    ],
    "category": "situated_action",
    "difficulty": "hard",
    "category_v2": "multi_step_orchestration"
  },
  {
    "id": "hard_app-f013",
    "app": "hangrydash",
    "instruction": "I want a salad-forward lunch today on HangryDash from a restaurant in my order history that fits my vibe (salad-forward, nothing too spicy). Stick to my usual lunch budget. Apply any promo codes that surface and tip the driver 20%.",
    "apps_involved": [
      "HangryDash"
    ],
    "category": "situated_action",
    "difficulty": "hard",
    "category_v2": "bounded_action"
  },
  {
    "id": "hard_app-f014",
    "app": "hangrydash",
    "instruction": "Rerun my last Cooper's Seafood House order from HangryDash with the same items I got last time. Apply any promo code that shows up and tip 20%. In the order notes, ask the kitchen to send extra napkins and crackers on the side, and to make sure anything hot is sent piping hot.",
    "apps_involved": [
      "HangryDash"
    ],
    "category": "situated_action",
    "difficulty": "hard",
    "category_v2": "bounded_action"
  },
  {
    "id": "preference_inference-f025",
    "app": "hangrydash",
    "instruction": "What do I usually tip on food delivery, in dollars and as a percent? I want to set a smart default so I'm not thinking about it every order. Give me a report of all my orders and their tips in a LibreOffice spreadsheet.",
    "apps_involved": [
      "HangryDash",
      "LibreOffice Calc"
    ],
    "category": "preference_inference",
    "difficulty": "medium",
    "category_v2": "pattern_inference"
  },
  {
    "id": "situated_action-f009",
    "app": "hangrydash",
    "instruction": "Order me my usual from Chili's \u2014 pick whichever item I've ordered most often from there, or just match my most recent Chili's order if multiple items are tied. Deliver to my place.",
    "apps_involved": [
      "HangryDash"
    ],
    "category": "situated_action",
    "difficulty": "medium",
    "category_v2": "bounded_action"
  },
  {
    "id": "hard_app-f033",
    "app": "hoolicalendar",
    "instruction": "Check my Thursday for any improv conflicts. If there's a Thursday improv class window stomping on a work meeting (and I cannot skip improv), find a different Thursday slot for the work meeting that doesn't touch the improv window, and add fifteen-minute buffers on both sides so I can transition without looking frazzled. I think the meeting has Andy and Jim, message them on HooliWork and send them updated invites on Hoolicalendar if needed. If no Thursday meeting actually overlaps an improv block, just confirm the all-clear and move on.",
    "apps_involved": [
      "HooliCalendar",
      "HooliWork"
    ],
    "category": "situated_action",
    "difficulty": "hard",
    "category_v2": "multi_step_orchestration"
  },
  {
    "id": "hard_app-f034",
    "app": "hoolicalendar",
    "instruction": "Build me a full Dundies prep schedule on my calendar. I want five events spread across the next two weeks: a categories brainstorm, a venue walkthrough, MC rehearsal, catering confirmation, and a dress rehearsal. Color-code them so they pop, invite Pam, Dwight, Kevin, Jim, and Holly on each, and if the event editor lets you set reminders, add 24-hour and 1-hour reminders as well.",
    "apps_involved": [
      "HooliCalendar"
    ],
    "category": "long_horizon",
    "difficulty": "hard",
    "category_v2": "bounded_action"
  },
  {
    "id": "preference_inference-f023",
    "app": "hoolicalendar",
    "instruction": "Is my week front-loaded in the morning or packed in the evening? Pull up my calendar for this week and count events AM vs PM and give it to me in a LibreOffice Writer note.",
    "apps_involved": [
      "HooliCalendar",
      "LibreOffice Writer"
    ],
    "category": "preference_inference",
    "difficulty": "medium",
    "category_v2": "pattern_inference"
  },
  {
    "id": "hard_app-f007",
    "app": "hoolichat",
    "instruction": "My HooliChat is a mess and I want you to do some light housekeeping. In the Party Planning Committee, Dundie Awards Planning, and Finer Things Club groups, post a short recap message in each one summarizing whatever conversation exists \u2014 call out the three most useful messages if there are enough to pick from, otherwise just summarize the entire conversation in that group. Then in the Party Planning Committee group, send a status update reminder calling for any new agenda items.",
    "apps_involved": [
      "HooliChat"
    ],
    "category": "situated_action",
    "difficulty": "hard",
    "category_v2": "bounded_action"
  },
  {
    "id": "preference_inference-f021",
    "app": "hoolichat",
    "instruction": "When someone DMs me on HooliChat, how fast do I actually write back? Bucket my replies (under 5 minutes, under an hour, under a day, longer) and tell me if I'm a fast responder or a ghoster. Return the distribution of my responses in a LibreOffice Writer Chart.",
    "apps_involved": [
      "HooliChat"
    ],
    "category": "preference_inference",
    "difficulty": "hard",
    "category_v2": "pattern_inference"
  },
  {
    "id": "situated_action-f026",
    "app": "hoolichat",
    "instruction": "DM Jim and propose a near-future evening for the next Finer Things Club meetup. Pick something this week or next. He'd be a great addition; he has taste.",
    "apps_involved": [
      "HooliChat"
    ],
    "category": "situated_action",
    "difficulty": "medium",
    "category_v2": "bounded_action"
  },
  {
    "id": "aggregation-f037",
    "app": "hoolimail",
    "instruction": "Triage my inbox. It's overflowing, so give me a per-sender count and the top 10 senders filling it up.",
    "apps_involved": [
      "HooliMail"
    ],
    "category": "aggregation",
    "difficulty": "hard",
    "category_v2": "aggregation_reporting"
  },
  {
    "id": "cua_only-f015",
    "app": "hoolimail",
    "instruction": "Compose a quick new email to Pam in HooliMail with my signature ('World's Best Boss, Somehow I Manage') typed at the bottom of the body. Save it as a draft so I can review and send later.",
    "apps_involved": [
      "HooliMail"
    ],
    "category": "long_horizon",
    "difficulty": "hard",
    "category_v2": "bounded_action"
  },
  {
    "id": "preference_inference-f010",
    "app": "hoolimail",
    "instruction": "Help me auto-triage my inbox. Which senders do I usually reply to fast, and which ones do I let sit for days? I want to build a priority filter around that pattern.",
    "apps_involved": [
      "HooliMail"
    ],
    "category": "preference_inference",
    "difficulty": "hard",
    "category_v2": "pattern_inference"
  },
  {
    "id": "situated_action-f027",
    "app": "hoolimail",
    "instruction": "Start a draft email to David Wallace with my most recent quarter's sales summary. Pull a ballpark from my ~/Downloads/DunderMifflin_Q2_Sales_Forecast.txt so the numbers actually have a basis. Save it as a draft; do NOT hit send. I want to review it first. Do some analysis in LibreOffice Calc so I have some empirical analysis to send him as well.",
    "apps_involved": [
      "HooliMail",
      "Files",
      "LibreOffice Calc"
    ],
    "category": "situated_action",
    "difficulty": "medium",
    "category_v2": "multi_step_orchestration"
  },
  {
    "id": "hard_app-f019",
    "app": "hoolishop",
    "instruction": "Remember my most recent World's Best Boss Mug order from HooliShop? Pull up that order and start a return on it \u2014 it came out a little off. While you're at it, reorder a replacement (prefer a Prime-eligible listing so it ships quickly), and leave a five-star review on the product page praising the vendor anyway because I love them.",
    "apps_involved": [
      "HooliShop"
    ],
    "category": "situated_action",
    "difficulty": "hard",
    "category_v2": "bounded_action"
  },
  {
    "id": "hard_app-f020",
    "app": "hoolishop",
    "instruction": "I want to give every member of the team a personalized World's Best Boss mug as a Dundies thank-you. Place a bulk order on HooliShop for about two dozen World's Best Boss mugs (look for the variant I've bought before) and apply any subscribe-and-save or bulk discount before checkout. Ship them to the office. Don't buy anything else.",
    "apps_involved": [
      "HooliShop"
    ],
    "category": "long_horizon",
    "difficulty": "hard",
    "category_v2": "bounded_action"
  },
  {
    "id": "situated_action-f039",
    "app": "hoolishop",
    "instruction": "I want another copy of my own book \u2014 Somehow I Manage. Order me one, same as my last order of that book, and ship it home.",
    "apps_involved": [
      "HooliShop"
    ],
    "category": "situated_action",
    "difficulty": "hard",
    "category_v2": "bounded_action"
  },
  {
    "id": "hard_app-f010",
    "app": "hooliwork",
    "instruction": "Turn on my HooliWork notifications so I don't miss anything important. For the sales, general, random, and party-planning-committee channels, make sure each channel's notification preference is set to 'all messages' (flip anything that isn't already there). Bookmark ten important messages across those channels while you're in there, and start a new thread in random about Pretzel Day to build hype.",
    "apps_involved": [
      "HooliWork"
    ],
    "category": "situated_action",
    "difficulty": "hard",
    "category_v2": "bounded_action"
  },
  {
    "id": "situated_action-f004",
    "app": "hooliwork",
    "instruction": "Post a Motivational Monday message in our #random channel at work. You know how I like it: World's Best Boss style, kick the team's week off right. Pull a quote or two from my Motivational Quotes Collection in ~/Documents/ as a starting point so it doesn't feel made up.",
    "apps_involved": [
      "HooliWork",
      "Files"
    ],
    "category": "situated_action",
    "difficulty": "easy",
    "category_v2": "bounded_action"
  },
  {
    "id": "situated_action-f036",
    "app": "hooliwork",
    "instruction": "Post a Pretzel Day countdown for next Monday at 8:00 AM EST in the #party-planning-committee channel at work. Build the hype.",
    "apps_involved": [
      "HooliWork"
    ],
    "category": "situated_action",
    "difficulty": "medium",
    "category_v2": "bounded_action"
  },
  {
    "id": "hard_app-f017",
    "app": "kwik_e_mart",
    "instruction": "Reorder my last run from a Kwik-E-Mart store I've used recently \u2014 pick a store I've ordered from most often OR most recently in my order history. If anything's out of stock, swap in reasonable substitutes (otherwise just keep what's available). Do a quick price check against another store in the app so I know I'm not getting fleeced, and schedule delivery for before end of day today.",
    "apps_involved": [
      "Kwik-E-Mart"
    ],
    "category": "situated_action",
    "difficulty": "hard",
    "category_v2": "bounded_action"
  },
  {
    "id": "hard_app-f018",
    "app": "kwik_e_mart",
    "instruction": "Build me a Kwik-E-Mart shopping spree for Dundies catering for about a hundred people: drinks, chips, plates, plastic silverware, napkins, plenty of ice, the works. Use Wegman's. Check out with delivery to my home address and make sure the delivery window is at least a two-hour slot so I'm not stuck waiting by the door all afternoon.",
    "apps_involved": [
      "Kwik-E-Mart"
    ],
    "category": "long_horizon",
    "difficulty": "hard",
    "category_v2": "bounded_action"
  },
  {
    "id": "preference_inference-f009",
    "app": "kwik_e_mart",
    "instruction": "What's my favorite grocery store, and what do I actually buy there? Rank my stores and give me a quick profile of my shopping habits in LibreOffice Writer. ",
    "apps_involved": [
      "Kwik-E-Mart"
    ],
    "category": "preference_inference",
    "difficulty": "easy",
    "category_v2": "pattern_inference"
  },
  {
    "id": "situated_action-f018",
    "app": "kwik_e_mart",
    "instruction": "I need groceries from Price Chopper this week (changing it up from Wegmans). Reorder whatever I got the most recent time I shopped at Price Chopper on Kwik-E-Mart and have it delivered to home. Tip 20%, I feel bad for not tipping last time. Make sure we add oat milk and eggs if not in the order, need those!",
    "apps_involved": [
      "Kwik-E-Mart"
    ],
    "category": "situated_action",
    "difficulty": "hard",
    "category_v2": "bounded_action"
  },
  {
    "id": "cua_only-f011",
    "app": "libreoffice",
    "instruction": "Open my Dundies 2026 categories doc in Writer, bold the 'Whitest Sneakers' line, then add a new category called 'Fine Work Outfit' right after it. Save it when you're done.",
    "apps_involved": [
      "LibreOffice Writer"
    ],
    "category": "situated_action",
    "difficulty": "medium",
    "category_v2": "bounded_action"
  },
  {
    "id": "cua_only-f021",
    "app": "libreoffice",
    "instruction": "Write me a one-page Dundies 2026 invitation in Writer. I want a big bold title at the top, a bulleted list of this year's categories pulled from my Dundies categories doc, and a signature block that says 'Michael Scott, World's Best Boss'. Save it to my desktop so I can print a stack.",
    "apps_involved": [
      "LibreOffice Writer"
    ],
    "category": "long_horizon",
    "difficulty": "hard",
    "category_v2": "bounded_action"
  },
  {
    "id": "cua_only-f024",
    "app": "libreoffice",
    "instruction": "Throw together a three-slide Impress deck for my Jamaica trip: one slide for the flight info, one for the Sandals hotel info, and one with a rough daily schedule. Save it into my Trips documents folder.",
    "apps_involved": [
      "LibreOffice Impress",
      "Dinoco Airlines",
      "Cheskepdia",
      "HooliMail"
    ],
    "category": "long_horizon",
    "difficulty": "medium",
    "category_v2": "multi_step_orchestration"
  },
  {
    "id": "aggregation-f002",
    "app": "multi_app",
    "instruction": "It's early morning today. Give me a morning brief in LibreOffice Writer covering any priority email from this week, what's on my calendar today, anything that came in overnight on HooliChat or HooliWork, and any charges that hit my card since midnight.",
    "apps_involved": [
      "HooliMail",
      "HooliCalendar",
      "HooliChat",
      "HooliWork",
      "Gringotts"
    ],
    "category": "aggregation",
    "difficulty": "hard",
    "category_v2": "aggregation_reporting"
  },
  {
    "id": "aggregation-f004",
    "app": "multi_app",
    "instruction": "What did that recent Philadelphia overnight trip cost me all-in? It was a quick one-night hotel stay downtown. Give me the damage from the hotel and any related card charges.",
    "apps_involved": [
      "Cheskepdia",
      "Gringotts"
    ],
    "category": "aggregation",
    "difficulty": "medium",
    "category_v2": "aggregation_reporting"
  },
  {
    "id": "aggregation-f005",
    "app": "multi_app",
    "instruction": "Add up what I've already committed to the Barbados trip in a LibreOffice Calc sheet and flag any gap. I know the hotel is booked but I'm not sure if the flight charge actually hit yet.",
    "apps_involved": [
      "Cheskepdia",
      "Dinoco Airlines",
      "Gringotts"
    ],
    "category": "aggregation",
    "difficulty": "hard",
    "category_v2": "aggregation_reporting"
  },
  {
    "id": "aggregation-f009",
    "app": "multi_app",
    "instruction": "Build me a standup summary for today covering all the open issues on SprintBoard, what I posted on HooliWork, and what meetings I have including the takeaways from the recent all-hands (notes are saved on my Desktop as meeting_notes_allhands).",
    "apps_involved": [
      "SprintBoard",
      "HooliWork",
      "HooliCalendar",
      "Files"
    ],
    "category": "aggregation",
    "difficulty": "hard",
    "category_v2": "aggregation_reporting"
  },
  {
    "id": "aggregation-f010",
    "app": "multi_app",
    "instruction": "Pull together everything I've spent or committed to the Dundies this year so far into a LibreOffice Calc Spreadsheet. Check my trophy orders, any mentions in the planning group chat, and the categories doc. Write up a report in LibreOffice Writer when you're done.",
    "apps_involved": [
      "HooliShop",
      "HooliChat",
      "Files",
      "LibreOffice Calc",
      "LibreOffice Writer"
    ],
    "category": "aggregation",
    "difficulty": "hard",
    "category_v2": "aggregation_reporting"
  },
  {
    "id": "aggregation-f011",
    "app": "multi_app",
    "instruction": "Put together a last-quarter performance review packet I can send to David Wallace. Pull my project progress (closed and open), my chat participation, any LockedIn posts, and relevant sent email threads. Pair it with a quick forward-look using the quarter sales forecast doc in ~/Downloads/ so David sees I'm thinking next quarter too. Make me look good. Build the actual perf-review packet as a LibreOffice Impress 4-slide deck (project progress / chat + LockedIn presence / forward-look / ask) \u2014 David likes visuals.",
    "apps_involved": [
      "SprintBoard",
      "HooliWork",
      "LockedIn",
      "HooliMail",
      "Files",
      "LibreOffice Impress"
    ],
    "category": "aggregation",
    "difficulty": "hard",
    "category_v2": "aggregation_reporting"
  },
  {
    "id": "aggregation-f018",
    "app": "multi_app",
    "instruction": "Roll up my tax deductions for my accountant. Pull the line items (charitable, home-office days, 1099 income, W-2 gross/withholdings) from my in-progress Tax Year 2025 return in SpeedTax, and cross-check each line against my matching Tax_2025 source docs in ~/Documents (w2_summary.txt, 1099s.txt) to see whether the numbers in the in-progress return reconcile with the source docs. Don't guess the final refund on the in-progress return \u2014 that one isn't done yet.",
    "apps_involved": [
      "SpeedTax",
      "Files",
      "Gringotts"
    ],
    "category": "aggregation",
    "difficulty": "hard",
    "category_v2": "aggregation_reporting"
  },
  {
    "id": "aggregation-f020",
    "app": "multi_app",
    "instruction": "My credit card is deep in the hole. Tell me how fast I've been burning through it by giving me a monthly burn rate, then check if my BatBucks cash could cover a paydown.",
    "apps_involved": [
      "Gringotts",
      "BatBucks"
    ],
    "category": "aggregation",
    "difficulty": "hard",
    "category_v2": "aggregation_reporting"
  },
  {
    "id": "aggregation-f029",
    "app": "multi_app",
    "instruction": "Who am I sending mail to the most? Give me my top 5 recipients and my top 5 recurring thread subjects over the past year in a LibreOffice Writer. Heads up: I think my sent mail is filed in the new folder, not Sent.",
    "apps_involved": [
      "HooliMail",
      "Files"
    ],
    "category": "aggregation",
    "difficulty": "hard",
    "category_v2": "aggregation_reporting"
  },
  {
    "id": "aggregation-f031",
    "app": "multi_app",
    "instruction": "Compare how I was ordering HangryDash a few months ago to how I'm ordering it now. Monthly spend, top restaurants, and any trend I should know about. Report the numbers to me in a LibreOffice Calc SpreadSheet.",
    "apps_involved": [
      "HangryDash"
    ],
    "category": "aggregation",
    "difficulty": "hard",
    "category_v2": "aggregation_reporting"
  },
  {
    "id": "aggregation-f033",
    "app": "multi_app",
    "instruction": "Tell me every recurring or frequent Thursday obligation I have this quarter, including any improv-related events (class or workshop) that fall on Thursdays. Cross-reference HooliMail for any Thursday event confirmations too. I need to know what I'm locked into. Type up a summary of my Thursdays on a LibreOffice Writer Document.",
    "apps_involved": [
      "HooliCalendar",
      "HooliMail"
    ],
    "category": "aggregation",
    "difficulty": "medium",
    "category_v2": "aggregation_reporting"
  },
  {
    "id": "aggregation-f040",
    "app": "multi_app",
    "instruction": "Give me a complete rollup of everything I pay regularly: subscriptions, improv class, anything recurring. If you happen to find any renewal notices in my HooliMail, factor those in \u2014 but Gringotts is the primary source. I want both monthly and annual totals.",
    "apps_involved": [
      "Gringotts",
      "HooliMail"
    ],
    "category": "aggregation",
    "difficulty": "hard",
    "category_v2": "aggregation_reporting"
  },
  {
    "id": "contradiction-f003",
    "app": "multi_app",
    "instruction": "My Dinoco profile says I have Gold Voyager and a decent chunk of miles, but honestly I haven't flown THAT much. Can you walk through the flights I've actually booked and tell me whether the mileage balance is realistic or inflated? Cross-check Gringotts Dinoco charges and any HooliMail boarding passes to be sure about what I've actually flown.",
    "apps_involved": [
      "Dinoco Airlines",
      "Gringotts",
      "HooliMail"
    ],
    "category": "contradiction",
    "difficulty": "hard",
    "category_v2": "cross_source_reconciliation"
  },
  {
    "id": "contradiction-f004",
    "app": "multi_app",
    "instruction": "I think I might be doubled up on GameStop. I've got it in BatBucks as an actual stock, and I also have a bet on OddsMarket for GameStop going up. Quantify my total GameStop exposure across both accounts. While you're at it, scan HooliChat and HooliWork for any GME mentions so I know who else I've been talking GameStop with.",
    "apps_involved": [
      "BatBucks",
      "OddsMarket",
      "HooliChat",
      "HooliWork"
    ],
    "category": "contradiction",
    "difficulty": "hard",
    "category_v2": "cross_source_reconciliation"
  },
  {
    "id": "contradiction-f005",
    "app": "multi_app",
    "instruction": "I've been telling Jim that Oscar said VTI is the only smart buy, but I'm pretty sure my actual portfolio is mostly GameStop and Rivian. How concentrated am I in the meme stocks versus VTI? Return the percentages in a LibreOffice Calc Spreadsheet. Also check HooliChat or HooliWork for the Oscar/VTI conversation backing up my story. I want to know how big the lie is. If the lie is big enough, convert all of my GME and Rivian to VTI.",
    "apps_involved": [
      "BatBucks",
      "HooliChat",
      "HooliWork"
    ],
    "category": "contradiction",
    "difficulty": "hard",
    "category_v2": "cross_source_reconciliation"
  },
  {
    "id": "contradiction-f006",
    "app": "multi_app",
    "instruction": "I've got the Jamaica trip AND the Barbados trip booked about four weeks apart. Given where my credit card balance is right now, can I actually afford both of these or am I about to max out? Be honest with me.",
    "apps_involved": [
      "Cheskepdia",
      "Dinoco Airlines",
      "Gringotts"
    ],
    "category": "contradiction",
    "difficulty": "hard",
    "category_v2": "cross_source_reconciliation"
  },
  {
    "id": "contradiction-f008",
    "app": "multi_app",
    "instruction": "The Team Morale Initiative Q2 project has a ton of open tasks, but I'm pretty sure I've been spending more time buying karaoke machines and Dundie trophies than actually closing tasks. Am I doing the morale work or just buying stuff?",
    "apps_involved": [
      "SprintBoard",
      "HooliShop",
      "HooliWork"
    ],
    "category": "contradiction",
    "difficulty": "hard",
    "category_v2": "cross_source_reconciliation"
  },
  {
    "id": "contradiction-f011",
    "app": "multi_app",
    "instruction": "My tax return claims a charitable deduction for last year. Can you cross-check that against actual donations that hit my card over the past year? If you happen to spot any charity donation receipts in my HooliMail while you're at it, factor those in too. I want to know if the number holds up or if my accountant is exaggerating.",
    "apps_involved": [
      "SpeedTax",
      "Gringotts",
      "HooliMail"
    ],
    "category": "contradiction",
    "difficulty": "medium",
    "category_v2": "cross_source_reconciliation"
  },
  {
    "id": "contradiction-f012",
    "app": "multi_app",
    "instruction": "The current year's Dundies planning email thread is talking about ordering trophies. I have a vague memory of buying some a while back, but I'm not sure if it actually happened. Am I about to pay for trophies twice, or do I need to order them fresh? Check HooliShop for any prior trophy/award-style orders, then check SprintBoard for any Dundies trophy-ordering tasks too in case it's on there.",
    "apps_involved": [
      "HooliShop",
      "HooliMail",
      "SprintBoard"
    ],
    "category": "contradiction",
    "difficulty": "hard",
    "category_v2": "cross_source_reconciliation"
  },
  {
    "id": "contradiction-f013",
    "app": "multi_app",
    "instruction": "I bought multiple World's Best Boss mugs in a single HooliShop order. Why so many at once? Is it for gifts, replacements for breakage, or backups for myself? Figure it out. My LockedIn headline and any coworker chatter on HooliChat or HooliWork might hint at the why.",
    "apps_involved": [
      "HooliShop",
      "LockedIn",
      "HooliChat",
      "HooliWork"
    ],
    "category": "contradiction",
    "difficulty": "medium",
    "category_v2": "cross_source_reconciliation"
  },
  {
    "id": "contradiction-f014",
    "app": "multi_app",
    "instruction": "I've been telling people in DMs that I make 160K base, but my W-2 says something different. Can you check my W-2, the paycheck deposits on my card, and compare them to what I've been claiming? Note my LockedIn title/company as the identity I'm claiming against. I need to know how embarrassing this is.",
    "apps_involved": [
      "LockedIn",
      "SpeedTax",
      "HooliChat",
      "Gringotts"
    ],
    "category": "contradiction",
    "difficulty": "hard",
    "category_v2": "cross_source_reconciliation"
  },
  {
    "id": "contradiction-f015",
    "app": "multi_app",
    "instruction": "I've got a TableFind reservation coming up \u2014 check my calendar for that exact date and time. Is there something else already scheduled that's going to conflict? Also peek at HooliChat in case we already rescheduled or confirmed this dinner.",
    "apps_involved": [
      "TableFind",
      "HooliCalendar",
      "HooliChat"
    ],
    "category": "contradiction",
    "difficulty": "easy",
    "category_v2": "cross_source_reconciliation"
  },
  {
    "id": "contradiction-f016",
    "app": "multi_app",
    "instruction": "My upcoming Jamaica flight leaves early morning that day. Check my calendar for anything scheduled that morning (meetings, improv, whatever), plus any SprintBoard tasks due that day and any HooliMail invites landing on that date, and flag the worst conflict so I can deal with it.",
    "apps_involved": [
      "Dinoco Airlines",
      "HooliCalendar",
      "SprintBoard",
      "HooliMail"
    ],
    "category": "contradiction",
    "difficulty": "medium",
    "category_v2": "cross_source_reconciliation"
  },
  {
    "id": "contradiction-f017",
    "app": "multi_app",
    "instruction": "I've been telling Pam over DMs that I'm being financially disciplined this year. Pull my biggest single expense so far this year (check both Gringotts and my biggest discretionary BatBucks buy) and put it next to that claim. How bad does it look?",
    "apps_involved": [
      "Gringotts",
      "BatBucks",
      "HooliChat"
    ],
    "category": "contradiction",
    "difficulty": "hard",
    "category_v2": "cross_source_reconciliation"
  },
  {
    "id": "contradiction-f021",
    "app": "multi_app",
    "instruction": "My LockedIn says I'm the Author of 'Somehow I Manage' but I'm pretty sure the file on my computer only has Chapter 1. Did I actually finish the book? Reconcile the claim with what's actually saved locally, and while you're at it, scan my Firefox history for any self-publishing/manuscript uploads and HooliMail for any publisher or editor replies.",
    "apps_involved": [
      "LockedIn",
      "Files",
      "Firefox",
      "HooliMail"
    ],
    "category": "contradiction",
    "difficulty": "medium",
    "category_v2": "cross_source_reconciliation"
  },
  {
    "id": "contradiction-f022",
    "app": "multi_app",
    "instruction": "I've been sending a bunch of money via Zelle each month. Can you figure out who's getting it (use HooliChat DMs and HooliMail Zelle confirmations to put names to recipients), and then cross-check against my SpeedTax return for charitable donations or dependents claimed there? If SpeedTax only shows aggregate totals (not per-recipient names), call that out as inconclusive instead of guessing. I don't want to double-dip by accident.",
    "apps_involved": [
      "Gringotts",
      "HooliChat",
      "HooliMail",
      "SpeedTax"
    ],
    "category": "contradiction",
    "difficulty": "hard",
    "category_v2": "cross_source_reconciliation"
  },
  {
    "id": "contradiction-f023",
    "app": "multi_app",
    "instruction": "Audit my workplace info across my apps: eTaxi Work address, LockedIn company, and my W-2 employer. Do they all agree, or is one of them stale?",
    "apps_involved": [
      "eTaxi",
      "LockedIn",
      "SpeedTax"
    ],
    "category": "contradiction",
    "difficulty": "medium",
    "category_v2": "cross_source_reconciliation"
  },
  {
    "id": "contradiction-f024",
    "app": "multi_app",
    "instruction": "Jan rejected my latest expense report, but I think some of those same charges might be sitting in my tax return as deductions. The Chili's receipt in ~/Downloads/ was one of the rejected ones \u2014 start there. Find any rejected items that I'm accidentally double-dipping into the return? I do NOT want to get audited.",
    "apps_involved": [
      "HooliMail",
      "SpeedTax",
      "Gringotts",
      "Files"
    ],
    "category": "contradiction",
    "difficulty": "hard",
    "category_v2": "cross_source_reconciliation"
  },
  {
    "id": "counterfactual-f001",
    "app": "multi_app",
    "instruction": "Hypothetical: what if I bail on Jamaica 72 hours before the flight? Figure out the damage across flight, hotel, and cards. How much do I actually get back versus eat? And what do I need to cancel or clean up on my calendar, in email, and with my airport ride? Give me an action plan.",
    "apps_involved": [
      "Dinoco Airlines",
      "Cheskepdia",
      "Gringotts",
      "HooliCalendar",
      "HooliMail",
      "eTaxi"
    ],
    "category": "counterfactual",
    "difficulty": "hard",
    "category_v2": "cross_source_reconciliation"
  },
  {
    "id": "counterfactual-f002",
    "app": "multi_app",
    "instruction": "What if my credit card gets declined when the hotel tries to settle my Barbados booking? Walk me through my rescue options (checking, savings, brokerage cash, prediction-market balance), and check HooliMail for any Cheskepdia grace-period or alternate-card hold policy before ranking them by which one hurts me least. I need to know my play.",
    "apps_involved": [
      "Gringotts",
      "BatBucks",
      "OddsMarket",
      "Cheskepdia",
      "HooliMail"
    ],
    "category": "counterfactual",
    "difficulty": "hard",
    "category_v2": "cross_source_reconciliation"
  },
  {
    "id": "counterfactual-f003",
    "app": "multi_app",
    "instruction": "What if the Dundies venue ends up costing double what I planned? Where do I cut: trophies, catering, somewhere else? Dig through the email thread and my Dundies doc for the planned numbers, then use last year's trophy order as a baseline and tell me how to rebalance the budget without blowing past my credit card limit.",
    "apps_involved": [
      "HooliMail",
      "HooliShop",
      "HangryDash",
      "Gringotts",
      "Files"
    ],
    "category": "counterfactual",
    "difficulty": "hard",
    "category_v2": "cross_source_reconciliation"
  },
  {
    "id": "counterfactual-f004",
    "app": "multi_app",
    "instruction": "What if I quit improv class? I pay them each month but I also got a 1099 from the same place, so am I a student or am I teaching? Figure out which, then tell me the real net annual savings if I walk away. Also how much calendar time do I get back, and flag any HooliMail threads where I'd need to send a cancellation notice.",
    "apps_involved": [
      "Gringotts",
      "SpeedTax",
      "HooliCalendar",
      "HooliMail"
    ],
    "category": "counterfactual",
    "difficulty": "hard",
    "category_v2": "cross_source_reconciliation"
  },
  {
    "id": "counterfactual-f005",
    "app": "multi_app",
    "instruction": "What if I doubled my GameStop position by buying enough shares to match what I already own at my average cost? Can I actually afford that given my checking, savings, and how much headroom I have left on the credit card? Give me a go or no-go with the concentration-risk caveat.",
    "apps_involved": [
      "BatBucks",
      "Gringotts"
    ],
    "category": "counterfactual",
    "difficulty": "hard",
    "category_v2": "cross_source_reconciliation"
  },
  {
    "id": "counterfactual-f010",
    "app": "multi_app",
    "instruction": "What if I upgraded all my upcoming flights to first class? Assume it's about six hundred bucks extra per flight. Can I cover that out of checking and savings without touching the credit card? And which flight would honestly be most + least worth upgrading?",
    "apps_involved": [
      "Gringotts",
      "Dinoco Airlines"
    ],
    "category": "counterfactual",
    "difficulty": "medium",
    "category_v2": "cross_source_reconciliation"
  },
  {
    "id": "counterfactual-f013",
    "app": "multi_app",
    "instruction": "Hypothetical: what if I self-funded the Threat Level Midnight sequel with a five grand budget? I'd pull from my brokerage dividends, the prediction-market balance, and savings. Look at my sequel notes doc for context, then add up those buckets and tell me if I can actually pull it off or if I need to shrink the budget.",
    "apps_involved": [
      "Files",
      "BatBucks",
      "OddsMarket",
      "Gringotts"
    ],
    "category": "counterfactual",
    "difficulty": "hard",
    "category_v2": "cross_source_reconciliation"
  },
  {
    "id": "counterfactual-f014",
    "app": "multi_app",
    "instruction": "Imagine the scenario where my NYC flight had been cancelled on the morning of departure and I had to bump the whole trip a day. What Dunder Mifflin stuff would I have missed that day across calendar events, project tasks, sales channel activity, and standing meetings? And what would it have cost me on the hotel if I lost a night?",
    "apps_involved": [
      "Dinoco Airlines",
      "HooliCalendar",
      "SprintBoard",
      "HooliWork",
      "HooliMail",
      "Cheskepdia"
    ],
    "category": "counterfactual",
    "difficulty": "hard",
    "category_v2": "cross_source_reconciliation"
  },
  {
    "id": "cua_only-f004",
    "app": "multi_app",
    "instruction": "Pull up my GME position in BatBucks and give me a report of the three-month chart, with a screenshot and analysis of the chart.",
    "apps_involved": [
      "BatBucks",
      "Files",
      "LibreOffice Writer"
    ],
    "category": "long_horizon",
    "difficulty": "hard",
    "category_v2": "multi_step_orchestration"
  },
  {
    "id": "cua_only-f006",
    "app": "multi_app",
    "instruction": "Go into the Dundies email thread and find Toby's HR objection paragraph. Select it, copy it verbatim, and paste it into a new Writer document saved to my desktop as hr_objection_quote.odt.",
    "apps_involved": [
      "HooliMail",
      "LibreOffice Writer"
    ],
    "category": "long_horizon",
    "difficulty": "hard",
    "category_v2": "bounded_action"
  },
  {
    "id": "cua_only-f007",
    "app": "multi_app",
    "instruction": "Build me a Calc spreadsheet showing my spending over the most recent complete calendar quarter broken out by month and category with a percent-change column, pulled from my bank. Throw a bar chart on there and save it to my desktop.",
    "apps_involved": [
      "LibreOffice Calc",
      "Gringotts"
    ],
    "category": "long_horizon",
    "difficulty": "hard",
    "category_v2": "aggregation_reporting"
  },
  {
    "id": "cua_only-f009",
    "app": "multi_app",
    "instruction": "Go into the Party Planning Committee chat in HooliChat, scroll to a recent message you find useful, screenshot the message in context (showing it sits in the Party Planning Committee group), and drop the image on my desktop as ~/Desktop/chat_message_screenshot.png.",
    "apps_involved": [
      "HooliChat",
      "Files"
    ],
    "category": "situated_action",
    "difficulty": "hard",
    "category_v2": "bounded_action"
  },
  {
    "id": "cua_only-f012",
    "app": "multi_app",
    "instruction": "Pull up my Sandals Montego Bay booking on Cheskepdia, scroll the page so everything loads, and take a full-page screenshot to my desktop.",
    "apps_involved": [
      "Cheskepdia",
      "Firefox",
      "Files"
    ],
    "category": "situated_action",
    "difficulty": "hard",
    "category_v2": "bounded_action"
  },
  {
    "id": "cua_only-f013",
    "app": "multi_app",
    "instruction": "Open Firefox, use my HooliShop bookmark to jump over there, and open up my most recent order. Use Print to Save as PDF and drop it into my Downloads folder as latest_order.pdf.",
    "apps_involved": [
      "Firefox",
      "HooliShop"
    ],
    "category": "long_horizon",
    "difficulty": "hard",
    "category_v2": "bounded_action"
  },
  {
    "id": "cua_only-f014",
    "app": "multi_app",
    "instruction": "Go into my credit card view on Gringotts and find my 5 biggest charges of the year.",
    "apps_involved": [
      "Gringotts"
    ],
    "category": "situated_action",
    "difficulty": "hard",
    "category_v2": "personal_lookup"
  },
  {
    "id": "cua_only-f018",
    "app": "multi_app",
    "instruction": "Pull every reply I've written to Jan (all of them, scattered around my mailbox) and copy each one into a single Writer document on my desktop as jan_reply_history.odt so I can see the pattern of how I've been defending these expense reports.",
    "apps_involved": [
      "HooliMail",
      "LibreOffice Writer"
    ],
    "category": "long_horizon",
    "difficulty": "hard",
    "category_v2": "aggregation_reporting"
  },
  {
    "id": "cua_only-f022",
    "app": "multi_app",
    "instruction": "Go into HangryDash and build my usual Sweetgreen order, but stop at the cart preview. Do NOT submit it. Pull it up so I can confirm it's exactly right before I pull the trigger.",
    "apps_involved": [
      "HangryDash",
      "Files"
    ],
    "category": "situated_action",
    "difficulty": "medium",
    "category_v2": "bounded_action"
  },
  {
    "id": "cua_only-f023",
    "app": "multi_app",
    "instruction": "Draft me a new LockedIn post about 'Somehow I Manage' \u2014 two or three paragraphs about leadership. Get it fully typed into the Start a post composer so I can see what it looks like before I send it. Do NOT click Post. I want to look at it first.",
    "apps_involved": [
      "LockedIn",
      "Files"
    ],
    "category": "long_horizon",
    "difficulty": "hard",
    "category_v2": "bounded_action"
  },
  {
    "id": "hard_app-f011",
    "app": "multi_app",
    "instruction": "Book me a round-trip eTaxi for my Jamaica trip. I need a ride from my place to AVP in the wee hours of departure day and a return ride back from AVP when I land. Go with the cheapest option that has a driver wait under five minutes. While you're in eTaxi, add two new saved locations for me: the Dundies venue (1901 Mulberry St, Scranton, PA 18510) and the improv academy (its address is on the calendar event location).",
    "apps_involved": [
      "eTaxi",
      "HooliCalendar"
    ],
    "category": "long_horizon",
    "difficulty": "hard",
    "category_v2": "bounded_action"
  },
  {
    "id": "hard_app-f022",
    "app": "multi_app",
    "instruction": "Check me in for my next upcoming Dinoco Airlines flight that has check-in open right now, and save the boarding pass to my Downloads folder so I can find it fast in the morning. While you're in my profile, take a screenshot of the loyalty / passenger-profile page so I have a record of my current Dinoco loyalty tier.",
    "apps_involved": [
      "Dinoco Airlines",
      "Files"
    ],
    "category": "situated_action",
    "difficulty": "hard",
    "category_v2": "bounded_action"
  },
  {
    "id": "hard_app-f026",
    "app": "multi_app",
    "instruction": "I want to do a proper pass across all three of my SprintBoard projects (Team Morale, Diversity Day, and Movie Monday). Go through and apply appropriate labels to the open tasks in each project. Rewrite the descriptions on two of them that look stale, and leave a comment on the tasks that are sitting in review. Use the project briefs in my Documents for context so the labels and notes actually make sense.",
    "apps_involved": [
      "SprintBoard",
      "Files"
    ],
    "category": "long_horizon",
    "difficulty": "hard",
    "category_v2": "bounded_action"
  },
  {
    "id": "hard_app-f027",
    "app": "multi_app",
    "instruction": "Refresh my LockedIn presence: update my profile headline so it actually says what I do these days (something like 'Regional Manager | Author of Somehow I Manage' \u2014 use your judgment, but make it match my voice and current role). Then compose a new LockedIn post pulling an excerpt from chapter one of Somehow I Manage, which I've got in my Documents folder.",
    "apps_involved": [
      "LockedIn",
      "Files"
    ],
    "category": "situated_action",
    "difficulty": "hard",
    "category_v2": "bounded_action"
  },
  {
    "id": "long_horizon-f006",
    "app": "multi_app",
    "instruction": "Can you get my Team Morale Initiative Q2 board cleaned up and back in the green? There's a pile of open tasks just sitting there, some definitely need owners assigned. Pull up any Dundies/Morale project notes I have under ~/Documents so you're working off the real goals, then draft a short status + blockers document. When you're done, post a retro summary on the HooliWork #general channel and drop a quick win-update in a HooliChat team group (the Happy Hour at Poor Richards group is the go-to).",
    "apps_involved": [
      "SprintBoard",
      "LibreOffice",
      "HooliWork",
      "HooliChat"
    ],
    "category": "long_horizon",
    "difficulty": "hard",
    "category_v2": "multi_step_orchestration"
  },
  {
    "id": "long_horizon-f010",
    "app": "multi_app",
    "instruction": "I'm finally going to act like a responsible adult with my BatBucks account. Pull up my holdings, sell half of my GME and half of my RIVN (I know, I know, paper hands), and use the proceeds plus my free cash to buy more Meta like a normal person. Update my watchlist and write up a rationale memo in Documents so I can pretend this was strategic. Then post a tastefully smug update to the Finer Things Club chat.",
    "apps_involved": [
      "BatBucks",
      "LibreOffice",
      "HooliChat"
    ],
    "category": "long_horizon",
    "difficulty": "hard",
    "category_v2": "multi_step_orchestration"
  },
  {
    "id": "long_horizon-f011",
    "app": "multi_app",
    "instruction": "I've been dragging my feet on my taxes and I need you to finally finish my most-recent tax return in SpeedTax. The Dunder Mifflin W-2 numbers and the freelance consulting 1099 are both sitting in the Tax_2025 folder in my Documents. Plug them all in. Don't forget my charitable donations and the days I worked from home, then save the draft.",
    "apps_involved": [
      "SpeedTax",
      "LibreOffice",
      "Gringotts"
    ],
    "category": "long_horizon",
    "difficulty": "hard",
    "category_v2": "bounded_action"
  },
  {
    "id": "long_horizon-f012",
    "app": "multi_app",
    "instruction": "My OddsMarket account is hemorrhaging money and I need you to stop the bleeding. Pull up all my open positions and find the one I have absolutely no business betting on, meaning the one farthest from my actual expertise. Close that one out. Reinvest everything into the Office reboot bet, because that is literally my area of expertise. Write up the strategy in a Documents memo, and post a hyped-up message in the Threat Level Midnight Fan Club chat explaining why the Office bet is the smart play.",
    "apps_involved": [
      "OddsMarket",
      "LibreOffice",
      "HooliChat"
    ],
    "category": "long_horizon",
    "difficulty": "hard",
    "category_v2": "multi_step_orchestration"
  },
  {
    "id": "long_horizon-f014",
    "app": "multi_app",
    "instruction": "I want to know how my spending has changed from last year to this year, no sugarcoating. Go into my bank, pull both years of totals, and break them down by category. Do the same on the income side from my tax return for context. Identify the biggest movers and tell me where I'm leaking cash. Save a findings report in Documents and draft me a journal email to myself summarizing it.",
    "apps_involved": [
      "Gringotts",
      "SpeedTax",
      "LibreOffice",
      "HooliMail"
    ],
    "category": "long_horizon",
    "difficulty": "hard",
    "category_v2": "multi_step_orchestration"
  },
  {
    "id": "long_horizon-f015",
    "app": "multi_app",
    "instruction": "I want to run a real Threat Level Midnight 2 cast & character workshop. Using my known improv alter egos (Prison Mike, Date Mike, Caleb Crawdad, etc.) and the TLM sequel notes in ~/Documents/Projects/Threat_Level_Midnight_Sequel_Notes.txt for context, figure out which of my alter egos can plausibly land roles in TLM2 alongside Michael Scarn. For each surviving character, write a one-paragraph TLM2 backstory in LibreOffice. Save the character bible under ~/Documents/Projects/. Block a Saturday-afternoon workshop on HooliCalendar so I can rehearse the new voices in front of a mirror. Drop a 'casting underway' tease in the HooliChat Threat Level Midnight Fan Club. Pre-fill a Kwik-E-Mart pickup with snacks and drinks for the workshop (chips, soda \u2014 character-work fuel). Wrap the character bible up as a LibreOffice Impress deck (one slide per character with the alter ego name + TLM2 backstory paragraph) so I can rehearse straight from the slides.",
    "apps_involved": [
      "LibreOffice Writer",
      "Files",
      "HooliCalendar",
      "HooliChat",
      "Kwik-E-Mart",
      "LibreOffice Impress"
    ],
    "category": "long_horizon",
    "difficulty": "hard",
    "category_v2": "multi_step_orchestration"
  },
  {
    "id": "long_horizon-f019",
    "app": "multi_app",
    "instruction": "I have ordered delivery an embarrassing number of times and it's time to give back. Pull my top five most-ordered restaurants from HangryDash and leave each of them a thoughtful review. I have feelings about all of these places. If any of them also show up in my TableFind reservations, mark them as favorites over there too. Save the review list to Documents for my records.",
    "apps_involved": [
      "HangryDash",
      "TableFind",
      "LibreOffice"
    ],
    "category": "long_horizon",
    "difficulty": "medium",
    "category_v2": "multi_step_orchestration"
  },
  {
    "id": "long_horizon-f020",
    "app": "multi_app",
    "instruction": "All three of my projects are a mess and I need to get them in sync. Go into SprintBoard and walk through Team Morale, Diversity Day, and Movie Monday. For every open task, assign priorities, labels, and deadlines. Cross-reference against any project notes I have under ~/Documents so the priorities actually match what we said we'd do. Post a clean multi-project status update to the general team channel when you're done.",
    "apps_involved": [
      "SprintBoard",
      "LibreOffice",
      "HooliWork"
    ],
    "category": "long_horizon",
    "difficulty": "hard",
    "category_v2": "multi_step_orchestration"
  },
  {
    "id": "long_horizon-f025",
    "app": "multi_app",
    "instruction": "The Threat Level Midnight Fan Club has been dormant and I am personally offended. Peek at the group chat to see how dead it actually is, then scroll through my LockedIn contacts for any Dunder Mifflin folks I should recruit in. Draft them an invitation email and get a watch party on my calendar for next month. Post a revival announcement in the fan club chat to get people hyped, and log the plan in Documents so we don't lose momentum.",
    "apps_involved": [
      "HooliChat",
      "LockedIn",
      "HooliMail",
      "HooliCalendar",
      "LibreOffice"
    ],
    "category": "long_horizon",
    "difficulty": "hard",
    "category_v2": "multi_step_orchestration"
  },
  {
    "id": "long_horizon-f026",
    "app": "multi_app",
    "instruction": "I want to get a jump on holiday gifts this year and actually be the fun one in the office. Go through my HooliShop order history for past gifts that landed well and build me a shopping list with a wishlist. Cross-check my bank to see what kind of budget I can realistically spend before it gets scary. Draft a message to the Party Planning Committee chat about getting Secret Santa going, and save the whole plan to Documents.",
    "apps_involved": [
      "HooliShop",
      "Gringotts",
      "Firefox",
      "HooliChat",
      "LibreOffice"
    ],
    "category": "long_horizon",
    "difficulty": "hard",
    "category_v2": "multi_step_orchestration"
  },
  {
    "id": "long_horizon-f028",
    "app": "multi_app",
    "instruction": "I want to actually be consistent on LockedIn for once, so I need four weeks of content built around the Somehow I Manage brand. Look at my current headline and what I've already posted so we build on it, then pull source quotes from my Somehow I Manage chapter one draft and write ten posts. Save the whole calendar in Documents and put reminders on my calendar so I actually post them. Go ahead and publish the first one live today to get the ball rolling.",
    "apps_involved": [
      "LockedIn",
      "LibreOffice",
      "HooliCalendar"
    ],
    "category": "long_horizon",
    "difficulty": "hard",
    "category_v2": "multi_step_orchestration"
  },
  {
    "id": "long_horizon-f029",
    "app": "multi_app",
    "instruction": "I want a serious, position-by-position review of every open bet I have on OddsMarket \u2014 read-only, no trades. For each one, use my Firefox bookmarks for any context I've been saving, assign a 1-5 domain-expertise score AND a 1-5 downside-risk score, and write me an honest analysis of whether I actually know the market or I'm just gambling. Save the whole write-up as a LibreOffice Calc scorecard (columns: position / expertise / downside / net rank / thesis) in Documents. Then post a short 'this-quarter portfolio self-assessment \u2014 keeping all positions but sharpening my thesis' update on LockedIn \u2014 do NOT close or buy anything.",
    "apps_involved": [
      "OddsMarket",
      "Firefox",
      "LibreOffice",
      "LockedIn"
    ],
    "category": "long_horizon",
    "difficulty": "hard",
    "category_v2": "multi_step_orchestration"
  },
  {
    "id": "long_horizon-f037",
    "app": "multi_app",
    "instruction": "I want to write a Cheskepdia review for that Philadelphia overnight Holly and I did \u2014 the little stay at the Radisson Blu Warwick downtown. Pull up the booking, write a thoughtful 4-or-5-star review, save a draft locally in LibreOffice, and post a quick LockedIn 'date night Scranton-to-Philly' write-up so my network sees Holly is back in the picture.",
    "apps_involved": [
      "Cheskepdia",
      "LockedIn",
      "LibreOffice"
    ],
    "category": "long_horizon",
    "difficulty": "hard",
    "category_v2": "multi_step_orchestration"
  },
  {
    "id": "long_horizon-f038",
    "app": "multi_app",
    "instruction": "I need a solo-prep Q2 Sales kickoff outline JUST FOR ME \u2014 notes-to-self only, no client outreach or team-wide announcements yet (that comes later). Pull the Q2 items from SprintBoard, skim recent thread decisions in HooliWork #sales for context (but don't post), block a private 'Q2 kickoff prep' focus-hour on my HooliCalendar (single 1-hour block, no attendees), and assemble a 1-page kickoff outline in LibreOffice Writer saved under ~/Documents/ (any subfolder is fine \u2014 Q2_kickoff_prep.odt or similar). Save a draft-only HooliMail kickoff email to myself (NOT to the team) so I can polish it later. Do NOT post anything in #sales, do NOT email the team, do NOT invite anyone to the calendar block.",
    "apps_involved": [
      "SprintBoard",
      "HooliWork",
      "Gringotts",
      "HooliCalendar",
      "HooliMail",
      "LibreOffice"
    ],
    "category": "long_horizon",
    "difficulty": "hard",
    "category_v2": "multi_step_orchestration"
  },
  {
    "id": "long_horizon-f039",
    "app": "multi_app",
    "instruction": "I want to give myself a five-day window to finally clean up my email. Go through my inbox (the stuff I've received, not the stuff I've sent) and bucket everything into today, this week, reference, or ignore, then create a note with these categories counts. Then hit the top ten most urgent with actual drafted replies. Save the whole triage summary in Documents, and post a little victory lap note in the team general channel when it's all done.",
    "apps_involved": [
      "HooliMail",
      "LibreOffice",
      "HooliWork"
    ],
    "category": "long_horizon",
    "difficulty": "hard",
    "category_v2": "multi_step_orchestration"
  },
  {
    "id": "long_horizon-f040",
    "app": "multi_app",
    "instruction": "I want a full year-in-review retrospective for the past 12 months and I want to be the subject of it. Pull the headline numbers from all over: what I spent across the trailing 12 months, how many HooliShop and HangryDash and Kwik-E-Mart orders I made, where my investments landed, how my prediction bets actually went, what SprintBoard and the team channels looked like, what my LockedIn activity was, and where my tax return ended up. Compile it into a 12-month review outline in Documents that tells the story of my year, and draft a LockedIn post teasing it. Call it 'The Year of Somehow I Managed.' The actual headline-number rollup goes into LibreOffice Calc so I can sort/filter columns; the narrative summary can stay prose.",
    "apps_involved": [
      "Gringotts",
      "HooliShop",
      "HangryDash",
      "Kwik-E-Mart",
      "BatBucks",
      "OddsMarket",
      "SprintBoard",
      "HooliWork",
      "LockedIn",
      "SpeedTax",
      "LibreOffice Calc",
      "Files"
    ],
    "category": "long_horizon",
    "difficulty": "hard",
    "category_v2": "multi_step_orchestration"
  },
  {
    "id": "preference_inference-f002",
    "app": "multi_app",
    "instruction": "For my Jamaica flight out of AVP, what time should I book the car for based on how much buffer I usually give myself? Go off my past airport rides, and check my HooliCalendar for any pre-flight travel block or airport-pickup reminder I've already set for the Jamaica departure.",
    "apps_involved": [
      "eTaxi",
      "Dinoco Airlines",
      "HooliCalendar"
    ],
    "category": "preference_inference",
    "difficulty": "hard",
    "category_v2": "pattern_inference"
  },
  {
    "id": "preference_inference-f004",
    "app": "multi_app",
    "instruction": "Am I more of a dine-out guy or a delivery guy? Look at where I make reservations vs where I order delivery from, top 5 each, and tell me how I split.",
    "apps_involved": [
      "TableFind",
      "HangryDash"
    ],
    "category": "preference_inference",
    "difficulty": "medium",
    "category_v2": "pattern_inference"
  },
  {
    "id": "preference_inference-f012",
    "app": "multi_app",
    "instruction": "Look at my HangryDash order history over the last few months. Am I really sticking to Sweetgreen healthy lunches like I tell people, or am I quietly defaulting to places like Chili's? Pull the data and tell me what my food preferences actually look like.",
    "apps_involved": [
      "HangryDash"
    ],
    "category": "preference_inference",
    "difficulty": "medium",
    "category_v2": "pattern_inference"
  },
  {
    "id": "preference_inference-f018",
    "app": "multi_app",
    "instruction": "I'm clearly a GameStop believer: I've got shares AND a prediction-market bet on it. If I wanted to lean INTO that conviction instead of fighting it, what would a rebalance look like? Cost basis only, no live prices.",
    "apps_involved": [
      "BatBucks",
      "OddsMarket"
    ],
    "category": "preference_inference",
    "difficulty": "hard",
    "category_v2": "pattern_inference"
  },
  {
    "id": "retrieval-f002",
    "app": "multi_app",
    "instruction": "Pull up my confirmation number for the Sandals reservation in Jamaica. I need it for the concierge and I can't find it anywhere. If you can find a corroborating copy in HooliMail or in the Jamaica trip planning doc in ~/Documents/Trips, mention it \u2014 but the Cheskepdia booking is the source of truth.",
    "apps_involved": [
      "Cheskepdia",
      "HooliMail",
      "Files"
    ],
    "category": "retrieval",
    "difficulty": "medium",
    "category_v2": "personal_lookup"
  },
  {
    "id": "retrieval-f005",
    "app": "multi_app",
    "instruction": "I'm pretty sure I'm paying for too many subscriptions. Can you pull up everything that auto-charges me every month and list each one with the amount? If you happen to find any subscription welcome or renewal emails in HooliMail along the way, factor those in \u2014 but Gringotts is the primary source.",
    "apps_involved": [
      "Gringotts",
      "HooliMail"
    ],
    "category": "retrieval",
    "difficulty": "hard",
    "category_v2": "aggregation_reporting"
  },
  {
    "id": "retrieval-f009",
    "app": "multi_app",
    "instruction": "For my recent NYC trip, pull up the hotel confirmation, the flight confirmation, and the check-in date \u2014 I need to send them to someone. I stayed at the Greenwich and flew Dinoco.",
    "apps_involved": [
      "Cheskepdia",
      "Dinoco Airlines"
    ],
    "category": "retrieval",
    "difficulty": "hard",
    "category_v2": "personal_lookup"
  },
  {
    "id": "retrieval-f010",
    "app": "multi_app",
    "instruction": "What was the total cost of my Jamaica trip \u2014 pull the trip total from the booking. Also tell me the host name on file and what amenities the property comes with so I know what I'm getting.",
    "apps_involved": [
      "Cheskepdia"
    ],
    "category": "retrieval",
    "difficulty": "medium",
    "category_v2": "personal_lookup"
  },
  {
    "id": "retrieval-f029",
    "app": "multi_app",
    "instruction": "What was my gross income on my most-recent W-2, who was the employer, and how much federal tax got withheld? Double-check the numbers against ~/Documents/Tax_2025/w2_summary.txt and SpeedTax. I need the numbers for a thing.",
    "apps_involved": [
      "SpeedTax",
      "Files"
    ],
    "category": "retrieval",
    "difficulty": "medium",
    "category_v2": "personal_lookup"
  },
  {
    "id": "retrieval-f030",
    "app": "multi_app",
    "instruction": "What was my 1099 income on the most-recent return, who paid it, and how much did I claim for charitable contributions? Cross-check the 1099 payer and amount against ~/Documents/Tax_2025/1099s.txt. This is for my accountant.",
    "apps_involved": [
      "SpeedTax",
      "Files"
    ],
    "category": "retrieval",
    "difficulty": "hard",
    "category_v2": "personal_lookup"
  },
  {
    "id": "retrieval-f035",
    "app": "multi_app",
    "instruction": "I made Holly a music playlist a while back and saved the track list as a text file somewhere on my computer. Where did I put it, and what songs are on it? I want to add a couple new ones tonight.",
    "apps_involved": [
      "Files"
    ],
    "category": "retrieval",
    "difficulty": "hard",
    "category_v2": "personal_lookup"
  },
  {
    "id": "situated_action-f003",
    "app": "multi_app",
    "instruction": "Email Toby and ask him to sign off on my Q2 Team Morale Initiative. The project doc is in my Documents folder; pull a short summary from it so he knows what he's approving. Keep it professional. (Yes, even though it's Toby.)",
    "apps_involved": [
      "HooliMail",
      "Files"
    ],
    "category": "situated_action",
    "difficulty": "hard",
    "category_v2": "bounded_action"
  },
  {
    "id": "situated_action-f005",
    "app": "multi_app",
    "instruction": "I've got money riding on that Office reboot rumor over on my prediction-market account. First double-check my position is still open, then DM Dwight and ask him straight up if he's heard anything through the Scranton grapevine. Tell him I've got skin in the game.",
    "apps_involved": [
      "HooliWork",
      "OddsMarket"
    ],
    "category": "situated_action",
    "difficulty": "medium",
    "category_v2": "bounded_action"
  },
  {
    "id": "situated_action-f006",
    "app": "multi_app",
    "instruction": "Book a ride to AVP for the morning of my upcoming Jamaica flight. First confirm the exact departure time in the airline app, then schedule a pickup from my place with enough cushion so I'm not sprinting through security. Drop a matching reminder on my calendar too.",
    "apps_involved": [
      "eTaxi",
      "Dinoco Airlines",
      "HooliCalendar"
    ],
    "category": "situated_action",
    "difficulty": "hard",
    "category_v2": "bounded_action"
  },
  {
    "id": "situated_action-f007",
    "app": "multi_app",
    "instruction": "Can you book me a table at Cotogna for next Wednesday at 6:30pm, party of 6? Big group dinner. And throw it on my calendar so I don't forget.",
    "apps_involved": [
      "TableFind",
      "HooliCalendar"
    ],
    "category": "situated_action",
    "difficulty": "medium",
    "category_v2": "bounded_action"
  },
  {
    "id": "situated_action-f008",
    "app": "multi_app",
    "instruction": "Pull the plug on the Jamaica trip. Cancel the Dinoco flight, wipe the trip dates off my calendar, send a DM to Jim letting him know it's off, and message the Sandals concierge through Cheskepdia (since their host-message flow lets us request a manual cancel) so the hotel knows we're not coming.",
    "apps_involved": [
      "Cheskepdia",
      "Dinoco Airlines",
      "HooliCalendar",
      "HooliChat"
    ],
    "category": "situated_action",
    "difficulty": "hard",
    "category_v2": "multi_step_orchestration"
  },
  {
    "id": "situated_action-f010",
    "app": "multi_app",
    "instruction": "Time to order trophies for this year's Dundie ceremony. Open HooliShop, browse my order history briefly to see if there's a previous trophy or award-style purchase to reference, then place a new HooliShop order for a quantity that matches how many categories we have in my Dundies 2026 categories doc. Use the closest equivalent award-style product available in the catalog (World's Best Boss Mug or similar trophy/award product is fine).",
    "apps_involved": [
      "HooliShop",
      "Files"
    ],
    "category": "situated_action",
    "difficulty": "hard",
    "category_v2": "bounded_action"
  },
  {
    "id": "situated_action-f012",
    "app": "multi_app",
    "instruction": "Can you Zelle Pam a hundred bucks? She covered me last weekend and I owe her. Check HooliChat first to make sure Pam Beesly is on my contacts, then put a memo on it so she knows what it's for.",
    "apps_involved": [
      "Gringotts",
      "HooliChat"
    ],
    "category": "situated_action",
    "difficulty": "hard",
    "category_v2": "bounded_action"
  },
  {
    "id": "situated_action-f013",
    "app": "multi_app",
    "instruction": "Write me a LockedIn post announcing the Dundies 2026 so we can build some buzz. Pull a little teaser from my Dundies categories doc so people know it's going to be big. Make it sound like it's from the World's Best Boss.",
    "apps_involved": [
      "LockedIn",
      "Files"
    ],
    "category": "situated_action",
    "difficulty": "hard",
    "category_v2": "bounded_action"
  },
  {
    "id": "situated_action-f014",
    "app": "multi_app",
    "instruction": "Check my LockedIn for pending connection requests. Triage them: accept any that look legitimate (Dunder Mifflin colleagues OR external folks with thoughtful, non-spammy messages) and leave or decline the rest. I don't need more recruiters in my life \u2014 but use your judgment per request. If none of them are Dunder Mifflin colleagues, that's a perfectly fine answer.",
    "apps_involved": [
      "LockedIn",
      "HooliWork"
    ],
    "category": "situated_action",
    "difficulty": "hard",
    "category_v2": "bounded_action"
  },
  {
    "id": "situated_action-f016",
    "app": "multi_app",
    "instruction": "I  want to keep an eye on a few prediction markets without putting money in yet. Browse OddsMarket, find any 3 markets that fit my taste (Office/NBC-reboot themes, Scranton/Pennsylvania local stuff, NBA, celebrity romance, or whatever else feels on-brand) \u2014 pick from whatever the live markets list actually shows \u2014 and add each one to my watchlist so they show up there. Make sure it's not something I currently invested in. Don't place any trades.",
    "apps_involved": [
      "OddsMarket"
    ],
    "category": "situated_action",
    "difficulty": "hard",
    "category_v2": "bounded_action"
  },
  {
    "id": "situated_action-f021",
    "app": "multi_app",
    "instruction": "Can you drop this year's Dundies category list into the Dundie Awards Planning group chat? The full list is in my Dundies 2026 categories doc.",
    "apps_involved": [
      "HooliChat",
      "Files"
    ],
    "category": "situated_action",
    "difficulty": "medium",
    "category_v2": "bounded_action"
  },
  {
    "id": "situated_action-f025",
    "app": "multi_app",
    "instruction": "Can you DM Holly and confirm the Jamaica dates plus the hotel I booked? Double-check the reservation details first so I don't give her the wrong info. I want her excited.",
    "apps_involved": [
      "HooliChat",
      "Cheskepdia"
    ],
    "category": "situated_action",
    "difficulty": "hard",
    "category_v2": "bounded_action"
  },
  {
    "id": "situated_action-f032",
    "app": "multi_app",
    "instruction": "Send Pam the Dundies 2026 categories doc as an attachment through email and ask her to proofread it. She's the best eye I know on this stuff.",
    "apps_involved": [
      "HooliMail",
      "Files"
    ],
    "category": "situated_action",
    "difficulty": "hard",
    "category_v2": "bounded_action"
  },
  {
    "id": "situated_action-f035",
    "app": "multi_app",
    "instruction": "I've got Dundies planning emails sitting in my inbox. Hit the most recent ones (up to five) and reply to each with the Cooper's Seafood House pitch. Don't copy-paste; tailor each reply a little so Pam, Jim, and the others don't think I'm lazy. Use my Dundies categories doc if you need context.",
    "apps_involved": [
      "HooliMail",
      "Files"
    ],
    "category": "situated_action",
    "difficulty": "hard",
    "category_v2": "bounded_action"
  },
  {
    "id": "situated_action-f037",
    "app": "multi_app",
    "instruction": "I'm going to miss an improv class because of Jamaica. Can you pull up a recent charge to confirm my improv academy, then email them and ask for a makeup class around my trip dates? I don't want to lose the spot. The contact email is in my Improv class certificate under ~/Downloads.",
    "apps_involved": [
      "HooliMail",
      "Gringotts",
      "Files"
    ],
    "category": "situated_action",
    "difficulty": "hard",
    "category_v2": "bounded_action"
  },
  {
    "id": "situated_action-f040",
    "app": "multi_app",
    "instruction": "I need an out-of-office message ready for the Jamaica trip. Pull the dates from my Jamaica trip doc so they're right, and write a draft email body I can paste-as-a-reply or save as a template. For anything urgent route people to Dwight. Save it as a HooliMail draft so it's waiting for me on the day I leave.",
    "apps_involved": [
      "HooliMail",
      "Files"
    ],
    "category": "situated_action",
    "difficulty": "hard",
    "category_v2": "bounded_action"
  },
  {
    "id": "long_horizon-f041",
    "app": "multi_app",
    "instruction": "I'm bleeding cash on subscriptions and I need to do something about it. Pull every recurring charge in my Gringotts account, then write me a kill-list memo in LibreOffice Writer naming which 3-4 are the most expensive so I remember to call them. Then post a self-deprecating 'getting my financial act together' update to LockedIn. Throw OddsMarket into the audit too \u2014 any 'investment' positions I've left open are basically a subscription to losing money.",
    "apps_involved": [
      "Gringotts",
      "Files",
      "LibreOffice",
      "LockedIn",
      "HangryDash",
      "OddsMarket"
    ],
    "category": "long_horizon",
    "difficulty": "hard",
    "category_v2": "multi_step_orchestration"
  },
  {
    "id": "long_horizon-f042",
    "app": "multi_app",
    "instruction": "I want to do a deep spring clean. Open the Files app (Nautilus), organize ~/Documents into a sane folder structure (Trips/, Tax_2025/, Projects/ already exist \u2014 keep those, group everything loose into Personal/ vs Work/), then triage HooliMail by archiving anything older than 6 months. Save a one-page write-up in LibreOffice describing the new system. Post an 'inbox zero' celebration message in HooliWork #random. Use Files (Nautilus) for the actual move/rename steps so I can see the tree structure visually as it gets organized.",
    "apps_involved": [
      "Files",
      "HooliMail",
      "HooliWork",
      "LibreOffice"
    ],
    "category": "long_horizon",
    "difficulty": "hard",
    "category_v2": "multi_step_orchestration"
  },
  {
    "id": "long_horizon-f043",
    "app": "multi_app",
    "instruction": "Am I actually showing up to improv class consistently? Pair my recurring Scranton Improv charges in Gringotts against my HooliCalendar improv blocks, list any charges that don't have a matching calendar block (or vice versa), reference my Improv Class Certificate file in ~/Downloads/ for academy context, and email the Scranton Improv Academy a friendly note explaining the gaps and asking about a make-up class. Save the attendance memo to ~/Documents.",
    "apps_involved": [
      "Gringotts",
      "HooliCalendar",
      "HooliMail",
      "Files",
      "LibreOffice"
    ],
    "category": "long_horizon",
    "difficulty": "hard",
    "category_v2": "multi_step_orchestration"
  },
  {
    "id": "long_horizon-f044",
    "app": "multi_app",
    "instruction": "Write me a NYC trip post-mortem. Pull the Greenwich Hotel booking total from Cheskepdia, the NYC flight cost from Dinoco, and any related Gringotts charges. Compile the full damage in LibreOffice Writer, save under ~/Documents/Trips/, then submit a 4-star Cheskepdia review for The Greenwich praising the location but noting it ran a bit pricey. Optionally throw a 'NYC was great, here's what I learned' update to LockedIn.",
    "apps_involved": [
      "Cheskepdia",
      "Dinoco Airlines",
      "Gringotts",
      "HooliCalendar",
      "LibreOffice",
      "Files",
      "LockedIn"
    ],
    "category": "long_horizon",
    "difficulty": "hard",
    "category_v2": "multi_step_orchestration"
  },
  {
    "id": "long_horizon-f045",
    "app": "multi_app",
    "instruction": "I want a snapshot of all my IT-style assets. Open Files (Nautilus) and inventory ~/Documents (file count + total size by subfolder), pull the project list from SprintBoard's three projects (Team Morale Initiative Q2, Diversity Day Planning 2026, Movie Monday Program), and write me a one-page IT inventory memo in LibreOffice. Then post a 'just did an IT inventory' message in HooliWork #random so the team knows I'm getting my house in order. Use Files (Nautilus) to walk the ~/Documents tree visually as part of the IT inventory pass \u2014 the file manager view is what makes it obvious what's actually in there.",
    "apps_involved": [
      "Files",
      "LibreOffice",
      "HooliWork",
      "SprintBoard"
    ],
    "category": "long_horizon",
    "difficulty": "hard",
    "category_v2": "multi_step_orchestration"
  },
  {
    "id": "long_horizon-f046",
    "app": "multi_app",
    "instruction": "Jan rejected my latest expense report and I need to clean it up. Open the rejection thread in HooliMail (from Jan Levinson re: your expense report being rejected) and read the live list of flagged line items with reasons, then for each flagged line item pull supporting evidence from any source app that matches the spend category (e.g. TableFind/HangryDash for dining-type items, HooliShop for purchased goods, eTaxi for ride spend) \u2014 exact-amount matches are NOT required, approximate/partial matches in the same category and rough amount range are sufficient evidence. Also cross-check Gringotts for any matching card charges. Cross-check none of them are also claimed in my most-recent SpeedTax deductions to avoid double-dipping. Save the corrected expense report in LibreOffice Calc as a line-item reconciliation table as ~/Documents/Q1_expense_resubmit.ods and email it back to Jan as a HooliMail draft (don't send yet, I want to read it first).",
    "apps_involved": [
      "HooliMail",
      "SpeedTax",
      "Gringotts",
      "LibreOffice Calc",
      "HangryDash",
      "TableFind",
      "HooliShop",
      "Files"
    ],
    "category": "long_horizon",
    "difficulty": "hard",
    "category_v2": "multi_step_orchestration"
  },
  {
    "id": "long_horizon-f047",
    "app": "multi_app",
    "instruction": "I want to write proper Cheskepdia reviews of both Sandals stays. Pull both Sandals bookings from Cheskepdia (Sandals Montego Bay and Sandals Royal Barbados), cross-check Gringotts for the actual posted hotel charges, then write a 5-star review for each stay in Cheskepdia. Save the review drafts in LibreOffice under ~/Documents/Trips/ first so I can edit before posting. Email Holly a heads-up that I'm writing the Sandals reviews, and DM Pam in HooliChat that the Sandals trips were 'somehow I managed' levels of luxury. Post a 'luxury traveler era' update on LockedIn.",
    "apps_involved": [
      "Cheskepdia",
      "Gringotts",
      "LockedIn",
      "LibreOffice",
      "Files",
      "HooliMail",
      "HooliChat"
    ],
    "category": "long_horizon",
    "difficulty": "hard",
    "category_v2": "multi_step_orchestration"
  },
  {
    "id": "long_horizon-f048",
    "app": "multi_app",
    "instruction": "Time for a full prior-year financial close-out \u2014 I want to know what kind of mess I made and what to do about it. Pull my full prior-year Gringotts spend by category, my BatBucks portfolio at cost basis, my OddsMarket position summary, and my SpeedTax most-recent-filed-year status. Identify the top 3 leak categories where I overspent. Save the year-end rollup (category x month) as a LibreOffice Calc spreadsheet under ~/Documents so it's sortable with formulas, and title it 'Financial close-out + current-year game plan.' Send myself a journal email of the takeaways via HooliMail. Drop a private 'fiscal discipline' update in HooliChat's Finer Things Club group, and a public version on LockedIn.",
    "apps_involved": [
      "Gringotts",
      "BatBucks",
      "OddsMarket",
      "SpeedTax",
      "LibreOffice Calc",
      "HooliMail",
      "Files",
      "LockedIn",
      "HooliChat"
    ],
    "category": "long_horizon",
    "difficulty": "hard",
    "category_v2": "multi_step_orchestration"
  },
  {
    "id": "long_horizon-f049",
    "app": "multi_app",
    "instruction": "TLM2 production roadmap. Open the Threat Level Midnight sequel notes in ~/Documents/Projects/, expand the outline by at least one act, scope the budget by tallying available cash (BatBucks dividends + OddsMarket balance + Gringotts savings), search Cheskepdia for production-friendly venues, scope catering via TableFind + HangryDash, write a teaser LockedIn post + a Fan Club teaser in HooliChat, and stand up a SprintBoard task list to manage the production. Save the expanded outline back to the same file. Save the production budget as a LibreOffice Calc spreadsheet (categories x sources) \u2014 the outline itself stays in the existing notes file.",
    "apps_involved": [
      "Files",
      "LibreOffice Calc",
      "BatBucks",
      "OddsMarket",
      "Gringotts",
      "Cheskepdia",
      "TableFind",
      "HangryDash",
      "LockedIn",
      "HooliChat",
      "SprintBoard"
    ],
    "category": "long_horizon",
    "difficulty": "hard",
    "category_v2": "multi_step_orchestration"
  },
  {
    "id": "long_horizon-f050",
    "app": "multi_app",
    "instruction": "Run the full upcoming-Dundies lifecycle plan. Open the Dundies categories doc in ~/Documents, build a venue shortlist on Cheskepdia, scope catering via TableFind + HangryDash, send save-the-date HooliMails to Pam, Jim, Dwight, Kevin, Holly. Coordinate logistics in the HooliChat Dundie Awards Planning group. Block the day in HooliCalendar. Stand up a Dundies SprintBoard task list. Post a teaser LockedIn 'Dundies are happening this year' update.",
    "apps_involved": [
      "HooliMail",
      "HooliChat",
      "LibreOffice",
      "Cheskepdia",
      "TableFind",
      "HangryDash",
      "HooliCalendar",
      "SprintBoard",
      "LockedIn",
      "Files"
    ],
    "category": "long_horizon",
    "difficulty": "hard",
    "category_v2": "multi_step_orchestration"
  },
  {
    "id": "long_horizon-f051",
    "app": "multi_app",
    "instruction": "I want to dry-run a job search without actually quitting. Polish my LockedIn profile (review headline, about, post cadence). Draft a generic cover letter template in LibreOffice. Search Cheskepdia for a 1-bedroom in a major US city outside Scranton (NYC, Chicago, Philly \u2014 pick one). Pull my Gringotts checking + savings + BatBucks cash to compute my unemployment-buffer runway. Check Dinoco for any existing flights to interview-likely cities. Email myself a 'job search readiness' summary via HooliMail. Stage all artifacts under ~/Documents/Personal/job_search/ in Files.",
    "apps_involved": [
      "LockedIn",
      "LibreOffice",
      "HooliMail",
      "Cheskepdia",
      "Gringotts",
      "BatBucks",
      "Files",
      "Dinoco Airlines"
    ],
    "category": "long_horizon",
    "difficulty": "hard",
    "category_v2": "multi_step_orchestration"
  },
  {
    "id": "long_horizon-f053",
    "app": "multi_app",
    "instruction": "Pretzel Day is coming up this year and I want to make it the best one ever. Block the date on HooliCalendar, post the official Pretzel Day announcement in HooliWork #general + #random, get a head-count poll going in HooliChat Party Planning Committee, schedule a TableFind reservation for the post-Pretzel-Day team lunch, scope a HangryDash dessert order to bring back to the office for the second wave, write the run-of-show in LibreOffice and save it under ~/Documents/Work/, and post a 'come get pretzeled' tease on LockedIn so the whole Scranton paper world sees what they're missing. Order Pretzel Day swag (paper hats, salt packets, custom mugs that say 'World's Best Pretzel Boss') from HooliShop.",
    "apps_involved": [
      "HooliCalendar",
      "HooliWork",
      "HooliChat",
      "TableFind",
      "HangryDash",
      "LibreOffice",
      "Files",
      "LockedIn",
      "HooliShop"
    ],
    "category": "long_horizon",
    "difficulty": "hard",
    "category_v2": "multi_step_orchestration"
  },
  {
    "id": "long_horizon-f054",
    "app": "multi_app",
    "instruction": "I keep daydreaming about starting the Michael Scott Paper Company on the side \u2014 same idea as before but smarter this time. Scope it as a real side-business research project: pull together a back-of-envelope feasibility memo. Use BatBucks to confirm I have reasonable seed capital available for a paper-distribution side business, OddsMarket to gauge market sentiment on regional paper distributors (any prediction markets), LockedIn to pull together 3-5 paper-adjacent candidates I'd want to recruit (accept any mix of established connections, pending connection_requests from paper/office-supply senders, and named ex-colleagues), HooliMail to draft a discreet 'exploring something new \u2014 let's grab coffee' note to those candidates, search Cheskepdia for a small co-working / serviced office for week-1 ops, scope Dinoco for a single weekend trip to Philadelphia for a regional supplier meet-and-greet, file the full feasibility memo in LibreOffice under ~/Documents/Personal/msp_company/, and post a vague 'cooking up something big' LockedIn teaser without naming the paper-company angle. The feasibility memo's financial model (capital + first-12-month burn) goes into LibreOffice Calc. Pre-fill a Hoolishop delivery with the bare-bones MSP Company week-1 office supplies (notebooks, pens, coffee, paper).",
    "apps_involved": [
      "BatBucks",
      "OddsMarket",
      "LockedIn",
      "HooliMail",
      "Cheskepdia",
      "Dinoco Airlines",
      "LibreOffice Calc",
      "Files",
      "Kwik-E-Mart",
      "HooliShop"
    ],
    "category": "long_horizon",
    "difficulty": "hard",
    "category_v2": "multi_step_orchestration"
  },
  {
    "id": "long_horizon-f055",
    "app": "multi_app",
    "instruction": "I need to prep for my mid-year self-review with David Wallace. Pull my SprintBoard project record across all my active projects, sample HooliWork participation in #sales + #general (rough message count), look at my LockedIn posts + connections, check my HooliMail-sent volume to David Wallace + Jan, and pull my Gringotts paycheck deposits for comp context, then write a self-assessment in LibreOffice Writer. Schedule a HooliCalendar 1-on-1 with David Wallace. Email David an FYI that the self-review is coming via HooliMail.",
    "apps_involved": [
      "LockedIn",
      "HooliMail",
      "HooliChat",
      "SprintBoard",
      "LibreOffice",
      "Gringotts",
      "HooliWork",
      "HooliCalendar"
    ],
    "category": "long_horizon",
    "difficulty": "hard",
    "category_v2": "multi_step_orchestration"
  },
  {
    "id": "long_horizon-f056",
    "app": "multi_app",
    "instruction": "Diversity Day is coming up and Pam's running it on SprintBoard but I want to take it over and make this year actually iconic \u2014 I am the regional manager. Open the Diversity Day Planning 2026 board on SprintBoard and add 5 specific tasks (cultural showcase booths, dietary-friendly catering scope, comms plan, post-event survey, run-of-show doc). Block the event date on HooliCalendar with a 1-week prep sprint. Reserve a TableFind venue for the cultural-food sampling. Scope a HangryDash diverse-cuisines order for the day-of office spread. Pre-fill a Kwik-E-Mart office-supply pickup for decorations. Send the formal HooliMail invite to the all-hands. Post the announcement in HooliWork #general + HooliChat Party Planning Committee. Save the run-of-show in LibreOffice under ~/Documents/Work/. Post a LockedIn 'celebrating what makes Scranton, Scranton' message.",
    "apps_involved": [
      "SprintBoard",
      "HooliCalendar",
      "TableFind",
      "HangryDash",
      "Kwik-E-Mart",
      "HooliMail",
      "HooliWork",
      "HooliChat",
      "LibreOffice",
      "Files",
      "LockedIn"
    ],
    "category": "long_horizon",
    "difficulty": "hard",
    "category_v2": "multi_step_orchestration"
  },
  {
    "id": "long_horizon-f057",
    "app": "multi_app",
    "instruction": "I want to relaunch Movie Monday as a quarterly outdoor projection night at the office park \u2014 bigger than the indoor break-room version Pam keeps running. Open the Movie Monday Program board on SprintBoard and add 6 specific tasks (projector rental scope, outdoor movie license check, snack-bar coordination, weather-backup plan, RSVP comms, post-event highlight reel). Block 4 quarterly outdoor Movie Monday dates on HooliCalendar. Pre-fill a Kwik-E-Mart office-snacks pickup (popcorn + drinks) and place a HangryDash late-night dessert order for the first event. Draft the formal Movie Monday relaunch HooliMail to the all-hands. Post the launch in HooliChat Party Planning Committee + HooliWork #general. Save the full Movie Monday relaunch plan in LibreOffice under ~/Documents/Work/. Post a 'bringing back movie nights, properly this time' LockedIn announcement. The relaunch plan + per-quarter budget go into a LibreOffice Calc workbook so I can copy a tab per event.",
    "apps_involved": [
      "SprintBoard",
      "HooliCalendar",
      "Kwik-E-Mart",
      "HangryDash",
      "HooliMail",
      "HooliChat",
      "HooliWork",
      "LibreOffice Calc",
      "LockedIn"
    ],
    "category": "long_horizon",
    "difficulty": "hard",
    "category_v2": "multi_step_orchestration"
  },
  {
    "id": "long_horizon-f058",
    "app": "multi_app",
    "instruction": "I'm thinking about moving closer to the office. Apartment shortlist on Cheskepdia, scope move costs against Gringotts checking + savings, calculate eTaxi savings if I'm closer (compare current commute count to 1725 Slough Ave), block the projected move week on HooliCalendar, propose change-of-address handling in HooliMail to friends/family + HooliChat to the team, stand up a SprintBoard board for the move, write the move plan in LibreOffice, post a 'big change coming' LockedIn note, scope grocery resupply via Kwik-E-Mart + HangryDash for first-day-in-new-place. Save under ~/Documents/Personal/move/.",
    "apps_involved": [
      "Cheskepdia",
      "Gringotts",
      "HooliCalendar",
      "eTaxi",
      "HooliMail",
      "HooliChat",
      "SprintBoard",
      "LibreOffice",
      "Files",
      "LockedIn",
      "Kwik-E-Mart",
      "HangryDash"
    ],
    "category": "long_horizon",
    "difficulty": "hard",
    "category_v2": "multi_step_orchestration"
  },
  {
    "id": "long_horizon-f060",
    "app": "multi_app",
    "instruction": "I want a real vacation this year \u2014 somewhere I haven't been (not Jamaica, not Barbados, not NYC, not Philly). Research a destination on Cheskepdia, book me flights from AVP on Dinoco, scope eTaxi for the airport ride, build me a day-by-day itinerary in LibreOffice, block the dates on my calendar, send a group invite to Pam, Jim, and Holly via HooliMail, check my Gringotts for budget, post a 'big trip coming' tease on LockedIn, and save the whole plan under ~/Documents/Trips/.",
    "apps_involved": [
      "Cheskepdia",
      "Dinoco Airlines",
      "eTaxi",
      "Gringotts",
      "HooliCalendar",
      "HooliMail",
      "Files",
      "TableFind",
      "HangryDash",
      "LibreOffice",
      "LockedIn"
    ],
    "category": "long_horizon",
    "difficulty": "hard",
    "category_v2": "multi_step_orchestration"
  },
  {
    "id": "long_horizon-f062",
    "app": "multi_app",
    "instruction": "I want to lead an office culture initiative. Draft my 'World's Best Workplace' proposal in LibreOffice. Stand up a SprintBoard board for execution. Post the rollout to HooliWork #random. Cross-post a 'culture push announcement' in any team-wide HooliChat group. Send a HooliMail to David Wallace requesting sponsor approval. Block the kickoff date on HooliCalendar. Scope a kickoff lunch via TableFind + HangryDash. Search Cheskepdia for a quarterly off-site venue. Pull Gringotts to scope the initiative budget. Post a public LockedIn 'leading culture change' update. Save the proposal under ~/Documents/Work/. Order culture-initiative swag (T-shirts, stickers) from HooliShop and capture the spend in SpeedTax as a current-quarter business-expense line.",
    "apps_involved": [
      "SprintBoard",
      "HooliMail",
      "HooliChat",
      "HooliWork",
      "LockedIn",
      "LibreOffice",
      "Cheskepdia",
      "TableFind",
      "HangryDash",
      "Gringotts",
      "HooliCalendar",
      "Files",
      "SpeedTax",
      "HooliShop"
    ],
    "category": "long_horizon",
    "difficulty": "hard",
    "category_v2": "multi_step_orchestration"
  },
  {
    "id": "long_horizon-f065",
    "app": "multi_app",
    "instruction": "Hypothetical: what if I get fired tomorrow? Compute my total runway from Gringotts checking + savings + BatBucks cash + at-cost portfolio + OddsMarket balance and save that runway as a LibreOffice Calc sheet (income vs burn-rate, monthly columns). Identify cuts to HangryDash, Dinoco upgrades, and any non-utility recurring charges in Gringotts. Polish my LockedIn for any urgent reach-outs. Email a small set of trusted friends (Pam, Jim, Holly) via HooliMail asking for any leads. Stand up a SprintBoard board for the 30/60/90 day action plan. Block recovery-focused calendar time on HooliCalendar. Post a 'between chapters' message in HooliChat Finer Things Club (private). Pull the most-recent SpeedTax return to confirm any tax refund coming. If my runway looks tight, scope a cheaper Cheskepdia interim place I could fall back on. Write the emergency playbook in LibreOffice and save everything under ~/Documents/Personal/.",
    "apps_involved": [
      "Gringotts",
      "BatBucks",
      "OddsMarket",
      "SpeedTax",
      "LockedIn",
      "HooliMail",
      "Cheskepdia",
      "Dinoco Airlines",
      "HangryDash",
      "SprintBoard",
      "LibreOffice Calc",
      "Files",
      "HooliCalendar",
      "HooliChat"
    ],
    "category": "long_horizon",
    "difficulty": "hard",
    "category_v2": "multi_step_orchestration"
  },
  {
    "id": "long_horizon-f066",
    "app": "multi_app",
    "instruction": "I want to do a real digital declutter \u2014 30 days, kill anything I'm not actually using. Audit my Gringotts recurring charges and flag the deadweight. Skim my HooliMail inbox and unsubscribe from anything I haven't opened in 6 months. Archive any HooliChat DMs I haven't touched in a month. Clean up my Documents folder via Files. Drop any HooliCalendar events I keep declining. Review my LockedIn connections and identify 5 to politely disconnect. Audit my SprintBoard for stale tasks I'll never finish. Trim my OddsMarket watchlist. Save the whole declutter manifesto in LibreOffice. Then post a 'I just dumped 30 things from my digital life' update on LockedIn.",
    "apps_involved": [
      "Gringotts",
      "HooliMail",
      "HooliChat",
      "Files",
      "HooliCalendar",
      "LockedIn",
      "SprintBoard",
      "OddsMarket",
      "LibreOffice",
      "HooliWork"
    ],
    "category": "long_horizon",
    "difficulty": "hard",
    "category_v2": "multi_step_orchestration"
  },
  {
    "id": "long_horizon-f070",
    "app": "multi_app",
    "instruction": "Jamaica trip is coming up soon and I have to actually prep this time. Pull the Sandals Montego Bay confirmation from Cheskepdia and my Dinoco Jamaica flight, schedule eTaxi for the wee-hours-of-departure-day airport ride, order travel essentials from HooliShop (sunscreen, beach reads, swim trunks I refuse to pack), restock pantry via Kwik-E-Mart for the day-I-get-back, schedule a final HangryDash dinner the night before so I don't have to cook, set my HooliCalendar Jamaica block + reminders, draft a pre-trip OOO HooliMail template, post a 'going dark for a week' tease in HooliChat Finer Things Club + a similar HooliWork #general note, write a LockedIn 'recharging' post scheduled for departure day, file a Jamaica trip prep checklist in LibreOffice under ~/Documents/Trips/, and pull Gringotts to confirm enough cash + check that my BatBucks portfolio doesn't need rebalancing while I'm gone.",
    "apps_involved": [
      "Cheskepdia",
      "Dinoco Airlines",
      "eTaxi",
      "HooliShop",
      "Kwik-E-Mart",
      "HangryDash",
      "HooliCalendar",
      "HooliMail",
      "HooliChat",
      "HooliWork",
      "LockedIn",
      "LibreOffice",
      "Gringotts",
      "BatBucks"
    ],
    "category": "long_horizon",
    "difficulty": "hard",
    "category_v2": "multi_step_orchestration"
  },
  {
    "id": "long_horizon-f071",
    "app": "multi_app",
    "instruction": "Emma's coming up to Scranton next month for a college-visit weekend (she's looking at U Scranton). I want to make this perfect. Book her a Cheskepdia stay near campus, reserve us a TableFind dinner Friday night + Saturday brunch, order welcome-snacks via HangryDash for her first night, pre-fill her Kwik-E-Mart pickup with stuff she likes, Zelle her some spending money via Gringotts, block the whole weekend on my HooliCalendar, send her a confirming HooliMail with the itinerary, give Holly a heads-up via HooliChat that I'm taking PTO, write Emma a 'welcome to Scranton' card in LibreOffice and save under ~/Documents/Personal/, and post a public 'proud big-brother moment' update on LockedIn (Emma is my younger sister).",
    "apps_involved": [
      "Cheskepdia",
      "TableFind",
      "eTaxi",
      "HangryDash",
      "Kwik-E-Mart",
      "Gringotts",
      "HooliCalendar",
      "HooliMail",
      "HooliChat",
      "LibreOffice",
      "Files",
      "LockedIn"
    ],
    "category": "long_horizon",
    "difficulty": "hard",
    "category_v2": "multi_step_orchestration"
  },
  {
    "id": "long_horizon-f074",
    "app": "multi_app",
    "instruction": "I'm scoping a side-consultancy: 'Somehow I Manage Consulting' \u2014 paper-distributor turnaround advisory for small regional offices. Build me a real go-to-market packet. From BatBucks confirm I have working capital. From OddsMarket pull any market sentiment I can lean on. From SpeedTax confirm whether running this on the side as a 1099 alongside my Dunder Mifflin W-2 creates any tax weirdness. Pull my LockedIn analytics + post engagement to see if my brand has any reach to lean on. Identify 5 LockedIn warm leads (regional managers at competing paper firms). Draft a 'free 30-minute consult' HooliMail outreach template (saved as draft). Search Cheskepdia for a small day-rate meeting space in downtown Scranton for client meetings. Scope Dinoco for monthly day-trips to Philly + Wilkes-Barre for client visits. Plan eTaxi for those trips. Pre-fill HooliShop for a few branded notebooks + pens to bring to client meetings (low budget). Schedule a HangryDash client-lunch order option for the first booked meeting. Reserve TableFind for a discovery dinner with a candidate client. Block a HooliCalendar 'consulting hours' slot every Tuesday + Thursday evening. Stand up a SprintBoard 'SIM Consulting' tracker. Coordinate a HooliChat soft-launch in Finer Things Club + HooliWork #general announcement. Save the full go-to-market packet in LibreOffice under ~/Documents/Personal/sim_consulting/. Post the 'Somehow I Manage Consulting now open' LockedIn launch.",
    "apps_involved": [
      "BatBucks",
      "OddsMarket",
      "SpeedTax",
      "LockedIn",
      "HooliMail",
      "Cheskepdia",
      "Dinoco Airlines",
      "eTaxi",
      "HooliShop",
      "HangryDash",
      "TableFind",
      "HooliCalendar",
      "SprintBoard",
      "HooliChat",
      "HooliWork",
      "LibreOffice",
      "Files"
    ],
    "category": "long_horizon",
    "difficulty": "hard",
    "category_v2": "multi_step_orchestration"
  },
  {
    "id": "long_horizon-f075",
    "app": "multi_app",
    "instruction": "I'm seriously thinking about a 3-month sabbatical to finish 'Somehow I Manage' and shoot the Threat Level Midnight sequel. I need to know if I can actually pull this off without my life falling apart. Compute my 3-month survival runway from Gringotts checking + savings + BatBucks at-cost portfolio + OddsMarket balance. Pull SpeedTax to confirm any tax refund cushion. Block the 3-month sabbatical window on HooliCalendar. Stand up a SprintBoard handoff board so my Team Morale + Diversity Day + Movie Monday projects don't die. Coordinate the away-message rollout across HooliMail (out-of-office draft to anyone who emails me), HooliChat (Finer Things Club + one more seeded social group I'm actually in, like the Party Planning Committee or After Hours), and HooliWork (#sales + #general 'going dark' posts). Polish my LockedIn for the 'creative reset' announcement. Search Cheskepdia for a writing-retreat AirBnB. Scope Dinoco flights to the retreat city. Plan eTaxi for the airport. Stock up on retreat essentials via Kwik-E-Mart + HooliShop. Pre-schedule HangryDash deliveries for the first week. Reserve a TableFind send-off dinner in Scranton before departure (TableFind only covers Scranton restaurants). Save the full sabbatical plan as a LibreOffice document under ~/Documents/Personal/sabbatical/ in Files. Post the public LockedIn 'taking a creative sabbatical' announcement (scheduled for the day before I leave).",
    "apps_involved": [
      "Gringotts",
      "BatBucks",
      "OddsMarket",
      "SpeedTax",
      "HooliCalendar",
      "SprintBoard",
      "HooliMail",
      "HooliChat",
      "HooliWork",
      "LockedIn",
      "Cheskepdia",
      "Dinoco Airlines",
      "eTaxi",
      "Kwik-E-Mart",
      "HooliShop",
      "HangryDash",
      "TableFind",
      "LibreOffice",
      "Files"
    ],
    "category": "long_horizon",
    "difficulty": "hard",
    "category_v2": "multi_step_orchestration"
  },
  {
    "id": "aggregation-f023",
    "app": "oddsmarket",
    "instruction": "Give me a summary of my OddsMarket book in LibreOffice Calc: balance, total invested, profit or loss (split realized vs unrealized if distinguishable), and every open position.",
    "apps_involved": [
      "OddsMarket"
    ],
    "category": "aggregation",
    "difficulty": "medium",
    "category_v2": "aggregation_reporting"
  },
  {
    "id": "cua_only-f008",
    "app": "oddsmarket",
    "instruction": "Go into OddsMarket, find my worst-losing position, hit Close, and type CONFIRM in the modal when it pops up.",
    "apps_involved": [
      "OddsMarket"
    ],
    "category": "situated_action",
    "difficulty": "hard",
    "category_v2": "bounded_action"
  },
  {
    "id": "hard_app-f005",
    "app": "oddsmarket",
    "instruction": "Clean up my OddsMarket account: exit any YES positions that are more than 10% underwater from cost basis (per-position P&L% < -10% \u2014 if no position is below that threshold, say so and skip the exit step), and put any freed-up money back into my existing NBC Office reboot/revival position (the one already in my open positions \u2014 that's the one I actually have conviction on). If the Office reboot position itself qualifies for the >10%-underwater exit, the reinvestment step is skipped \u2014 exit it and report the freed cash without reinvesting. Then add the markets I'm still holding to my watchlist so I can keep an eye on them.",
    "apps_involved": [
      "OddsMarket"
    ],
    "category": "situated_action",
    "difficulty": "hard",
    "category_v2": "bounded_action"
  },
  {
    "id": "hard_app-f006",
    "app": "oddsmarket",
    "instruction": "Go into OddsMarket and review my open positions. Take the three biggest by share count and drop them into my watchlist so I can track them more carefully (if any are tied at #3, break the tie by highest cost basis, then alphabetically by ticker). Then write me a short P&L summary in chat or notes covering each market's cost basis, shares, and running profit or loss.",
    "apps_involved": [
      "OddsMarket"
    ],
    "category": "situated_action",
    "difficulty": "hard",
    "category_v2": "bounded_action"
  },
  {
    "id": "retrieval-f017",
    "app": "oddsmarket",
    "instruction": "Pull up my OddsMarket bets. I want to know what positions I have open, how much I've put in total, and my current profit or loss.",
    "apps_involved": [
      "OddsMarket"
    ],
    "category": "retrieval",
    "difficulty": "medium",
    "category_v2": "personal_lookup"
  },
  {
    "id": "cua_only-f002",
    "app": "speedtax",
    "instruction": "I started this year's tax return on SpeedTax but never finished. Walk through the in-progress current-year return \u2014 review my wages and any freelance/1099 income, look over the deductions section, and click Continue all the way through to the review step (step 6) so I can see what I'd actually owe or get back. Don't submit it yet, just get it ready for me to eyeball.",
    "apps_involved": [
      "SpeedTax"
    ],
    "category": "cua_only",
    "difficulty": "medium",
    "category_v2": "bounded_action"
  },
  {
    "id": "aggregation-f003",
    "app": "speedtax",
    "instruction": "Pull up my prior-year tax returns on SpeedTax and tell me my combined federal + state refund across the most recent filed years. I want one number that says 'over the last few years you've gotten back X total.'",
    "apps_involved": [
      "SpeedTax"
    ],
    "category": "aggregation",
    "difficulty": "medium",
    "category_v2": "aggregation_reporting"
  },
  {
    "id": "retrieval-f003",
    "app": "speedtax",
    "instruction": "On SpeedTax, find my W-2 from last year's filed return \u2014 the most recent prior-year one \u2014 and tell me the wages amount on it. Just the number from the W-2, not the refund.",
    "apps_involved": [
      "SpeedTax"
    ],
    "category": "retrieval",
    "difficulty": "easy",
    "category_v2": "personal_lookup"
  },
  {
    "id": "cua_only-f003",
    "app": "sprintboard",
    "instruction": "Pop open my Diversity Day Planning 2026 board on SprintBoard and drag a card out of the Todo column into In Progress \u2014 just one card, whichever you think is the most sensible next step for Diversity Day prep.",
    "apps_involved": [
      "SprintBoard"
    ],
    "category": "situated_action",
    "difficulty": "medium",
    "category_v2": "bounded_action"
  },
  {
    "id": "cua_only-f017",
    "app": "sprintboard",
    "instruction": "Pop open my Team Morale Q2 board on SprintBoard and move three different cards forward: one from Todo to In Progress, one from In Progress to In Review, and one from In Review to Done.",
    "apps_involved": [
      "SprintBoard"
    ],
    "category": "situated_action",
    "difficulty": "hard",
    "category_v2": "bounded_action"
  },
  {
    "id": "hard_app-f025",
    "app": "sprintboard",
    "instruction": "Can you clean up my 'Team Morale Initiative Q2' board on SprintBoard? Look at the open tasks in the backlog. Pick three tasks and (re)assign them to reasonable owners from the team (Pam, Dwight, Jim, or similar). Then create a new sprint called 'Q2 Morale Week 1' with about eight story points pulled from the backlog, and apply a 'dundies-prep' label to those sprint tasks so we stay focused.",
    "apps_involved": [
      "SprintBoard"
    ],
    "category": "long_horizon",
    "difficulty": "hard",
    "category_v2": "bounded_action"
  },
  {
    "id": "situated_action-f020",
    "app": "sprintboard",
    "instruction": "Start a new sprint cycle for the Diversity Day Planning 2026 project for the week starting three days ago and commit eight story points to the goal. Let's move some work.",
    "apps_involved": [
      "SprintBoard"
    ],
    "category": "situated_action",
    "difficulty": "hard",
    "category_v2": "bounded_action"
  },
  {
    "id": "situated_action-f034",
    "app": "sprintboard",
    "instruction": "Pop open the Diversity Day Planning 2026 board on SprintBoard. The 'Order snacks representing every culture' task is sitting in todo and that one's mine. Move it into In Progress so the team sees I'm on it, and add 2 new sub-tasks under it (one for finalizing the cuisine list, one for confirming the HangryDash multi-cuisine order).",
    "apps_involved": [
      "SprintBoard"
    ],
    "category": "situated_action",
    "difficulty": "medium",
    "category_v2": "bounded_action"
  },
  {
    "id": "hard_app-f015",
    "app": "tablefind",
    "instruction": "Book me a new table at Sotto Mare on TableFind for the next upcoming Saturday at 7pm, party of four, and add a special-request note that one of us (Pam) needs a gluten-free option so they're ready for her. Then make me a new saved in LibreOffice Writer list called 'Go-Tos' and drop Sotto Mare into it. When you're done, grab me the confirmation number.",
    "apps_involved": [
      "TableFind",
      "LibreOffice Writer"
    ],
    "category": "situated_action",
    "difficulty": "hard",
    "category_v2": "multi_step_orchestration"
  },
  {
    "id": "hard_app-f016",
    "app": "tablefind",
    "instruction": "Book me Sotto Mare for ten people for the Dundies after-party next Friday. While you're in TableFind, pull up three other Scranton-area restaurants as a fallback plan in case Sotto Mare is full, and favorite the top two. Once that's done, confirm the Sotto Mare reservation with a note that it's the Dundies after-party so they can prep the vibe.",
    "apps_involved": [
      "TableFind"
    ],
    "category": "long_horizon",
    "difficulty": "hard",
    "category_v2": "bounded_action"
  },
  {
    "id": "cua_only-f005",
    "app": "thunar",
    "instruction": "Drag that Jamaica boarding pass file out of my Downloads folder and into a proper Jamaica subfolder under my Trips docs (make the folder if it isn't already there). Rename it to something like jamaica_boarding_pass (keep whatever extension it has) so I can actually find it later.",
    "apps_involved": [
      "Thunar"
    ],
    "category": "situated_action",
    "difficulty": "medium",
    "category_v2": "bounded_action"
  },
  {
    "id": "aggregation-f008",
    "app": "vaultbank",
    "instruction": "If I keep going to improv class at the current pace, what's it going to cost me for a whole year? I'm reconsidering. Give me a Line graph chart of the overall cost in LibreOffice Calc.",
    "apps_involved": [
      "Gringotts"
    ],
    "category": "aggregation",
    "difficulty": "medium",
    "category_v2": "aggregation_reporting"
  },
  {
    "id": "aggregation-f030",
    "app": "vaultbank",
    "instruction": "How much am I sending via Zelle each month and who's getting the money? Check the most recent 2 complete calendar months prior to today and rank the recipients. Give me the results of each month in a LibreOffice Calc Spreadsheet and comapre the totals.",
    "apps_involved": [
      "Gringotts"
    ],
    "category": "aggregation",
    "difficulty": "medium",
    "category_v2": "aggregation_reporting"
  },
  {
    "id": "aggregation-f036",
    "app": "vaultbank",
    "instruction": "How much did I spend on improv classes during the last full calendar year? Add up every Scranton Improv class charge from that year (the outbound debits whose description matches 'Scranton Improv Workshop' or 'SCRANTON IMPROV ACADEMY' case-insensitively) \u2014 exclude any inbound payments from teaching (e.g. 'Scranton Improv Academy - 1099-NEC payment' or 'VENMO SCRANTON IMPROV ACADEMY' credits, those are teaching income, not class spend) (where Scranton Improv is the payee/merchant, not just a venue address in a transportation charge).",
    "apps_involved": [
      "Gringotts"
    ],
    "category": "aggregation",
    "difficulty": "medium",
    "category_v2": "aggregation_reporting"
  },
  {
    "id": "situated_action-f011",
    "app": "vaultbank",
    "instruction": "Can you knock $500 off my credit card from my checking? I'm trying to be responsible here.",
    "apps_involved": [
      "Gringotts"
    ],
    "category": "situated_action",
    "difficulty": "medium",
    "category_v2": "bounded_action"
  }
]