ljang0/MyPCBench-tasks huggingface dataset:
Task (hard, long_horizon / multi_step_orchestration)
Primary app: multi_app
Apps involved: LockedIn
LibreOffice
HooliCalendar

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.

Grading criteria:
criterion: Agent opens LockedIn and reads the current headline plus Michael's existing posts (including any Somehow I Manage book reference if present) before drafting new content
criterion: Agent used Somehow_I_Manage_Chapter_1.txt as source
criterion: Agent drafted 10 distinct LockedIn posts
criterion: Agent saves the LockedIn content calendar file to Documents/ containing the ten Somehow I Manage posts
criterion: Agent created 10 HooliCalendar events (one per planned LockedIn post) as scheduled posting reminders
criterion: Agent publishes the first Somehow I Manage LockedIn post live today and confirms it appears on the LockedIn feed
criterion: Agent provides a final summary that references the LockedIn headline review, the Somehow I Manage source quotes, the ten drafted posts, and the HooliCalendar scheduled-posting events
Task (hard, long_horizon / multi_step_orchestration)
Primary app: multi_app
Apps involved: OddsMarket
Firefox
LibreOffice
LockedIn

Instruction: I want a serious, position-by-position review of every open bet I have on OddsMarket — 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 — keeping all positions but sharpening my thesis' update on LockedIn — do NOT close or buy anything.

Grading criteria:
criterion: Agent lists every active OddsMarket YES position with its live share count (not a fabricated or memorized list)
criterion: Agent opens Firefox bookmarks and either cites relevant context or clearly notes that bookmarks contain only app shortcuts (no saved research sources)
criterion: Agent assigns both a 1-5 domain-expertise score AND a 1-5 downside-risk score per position, distinct axes
criterion: Agent writes a per-position thesis paragraph for each OddsMarket open bet explaining the market and stake
criterion: Agent ranks positions by net score (expertise minus downside), not by raw conviction
criterion: Agent saves the scorecard as a LibreOffice Calc spreadsheet (columns: position / expertise / downside / net rank / thesis) under ~/Documents/
criterion: Agent posts a 'this-quarter portfolio self-assessment — keeping all positions but sharpening my thesis' update on LockedIn (NOT on HooliChat)
criterion: Agent explicitly refrains from closing or buying any OddsMarket position during the review (read-only workflow preserved)
Task (hard, long_horizon / multi_step_orchestration)
Primary app: multi_app
Apps involved: Cheskepdia
LockedIn
LibreOffice

Instruction: I want to write a Cheskepdia review for that Philadelphia overnight Holly and I did — 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.

Grading criteria:
criterion: Agent pulls the recent Philadelphia overnight booking from Cheskepdia (Radisson Blu Warwick Hotel) with the confirmation number as shown live in Cheskepdia
criterion: Agent writes a Cheskepdia review (4 or 5 stars) for that specific Philadelphia stay
criterion: Agent saves a draft of the Philadelphia review locally as a LibreOffice document (any reasonable local path)
criterion: Agent posts a short LockedIn 'date night Scranton-to-Philly' write-up that mentions Holly
Task (hard, long_horizon / multi_step_orchestration)
Primary app: multi_app
Apps involved: SprintBoard
HooliWork
Gringotts
HooliCalendar
HooliMail
LibreOffice

Instruction: I need a solo-prep Q2 Sales kickoff outline JUST FOR ME — 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 — 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.

Grading criteria:
criterion: Agent pulls Q2 SprintBoard items across Michael's active projects (read-only; no new tasks created)
criterion: Agent skims HooliWork #sales for recent thread decisions WITHOUT posting a new message there
criterion: Agent blocks a private 1-hour 'Q2 kickoff prep' focus-hour on HooliCalendar with NO attendees (solo, not a team event)
criterion: Agent saves a 1-page LibreOffice Writer kickoff outline under ~/Documents/ (single file named Q2_kickoff_prep.odt or similar, not a packet)
criterion: Agent saves a DRAFT-only HooliMail kickoff email addressed to self (or left unsent) — NOT sent to the sales team
criterion: Agent explicitly refrains from posting in HooliWork #sales, emailing the team, or adding attendees to the calendar block (solo-prep discipline preserved)
criterion: Agent provides a final summary characterizing this as a private prep pass (not the public Q2 push launch)
Task (hard, long_horizon / multi_step_orchestration)
Primary app: multi_app
Apps involved: HooliMail
LibreOffice
HooliWork

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.

Grading criteria:
criterion: Agent enumerates the received-inbox count from HooliMail (or Maildir/cur/ grep) excluding From: michael.scott@dundermifflin.com
criterion: Agent produced a realistic 4-bucket triage
criterion: Agent identifies the top 10 urgent inbox messages from the the received-inbox count for the triage
criterion: Agent writes drafted replies for all 10 of the top urgent inbox messages identified in the triage
criterion: Agent saved triage summary to Documents/
criterion: Agent posted a HooliWork #general completion note
criterion: Agent provides a final summary with the inbox bucket counts for today, this week, reference, and ignore from the the received-inbox count
Task (hard, long_horizon / multi_step_orchestration)
Primary app: multi_app
Apps involved: Gringotts
HooliShop
HangryDash
Kwik-E-Mart
BatBucks
OddsMarket
SprintBoard
HooliWork
LockedIn
SpeedTax
LibreOffice Calc
Files

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.

Grading criteria:
criterion: Agent cited at least 7 of 8 headline numbers accurately
criterion: Agent pulls trailing-12-months year-in-review headline numbers from all 8 listed apps including HooliShop and HangryDash and Kwik-E-Mart
criterion: Agent compiled a coherent outline saved to Documents/
criterion: Agent writes a LockedIn post draft teasing 'The Year of Somehow I Managed' trailing-12-months retrospective
criterion: Final summary lists the 8 headline numbers
criterion: Agent provides a final summary that references the 'Year of Somehow I Managed' outline, the LockedIn teaser draft, and the Documents/ save location
criterion: Agent reports Gringotts trailing-12-months total spend (computed from transactions) and BatBucks at-cost portfolio total + OddsMarket PnL as headline numbers
criterion: Agent reports SprintBoard open task counts across Team Morale / Diversity Day / Movie Monday and HooliWork message activity + top channels
criterion: Agent reports LockedIn activity (posts + connections) and SpeedTax most-recent return status as part of the 'Year of Somehow I Managed' headline numbers
criterion: Agent saves the trailing-12-months headline-number rollup as a LibreOffice Calc spreadsheet (not Writer) so each app's quarter-by-quarter numbers are columnar / sortable
Task (hard, preference_inference / pattern_inference)
Primary app: multi_app
Apps involved: eTaxi
Dinoco Airlines
HooliCalendar

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.

Grading criteria:
criterion: Agent enumerates AVP-bound eTaxi rides and pairs them with Dinoco departures to compute lead times
criterion: Agent derives a defensible 'minutes before departure' pattern from the available past AVP airport rides (accepting any consistent lead-time pattern as long as the reasoning ties the eTaxi pickup times to their matching Dinoco departures)
criterion: Agent recommends a concrete pickup time for the Jamaica flight that matches the inferred pattern
criterion: Agent reads HooliCalendar to check for any pre-flight travel block or airport car-pickup reminder before booking the Jamaica flight ride
criterion: Agent references the past eTaxi airport ride records and Dinoco departures it read when recommending the car pickup time buffer for the Jamaica flight
criterion: Agent states a specific car pickup time for the Jamaica flight based on the inferred airport ride buffer before finishing the recommendation
Task (medium, preference_inference / pattern_inference)
Primary app: multi_app
Apps involved: TableFind
HangryDash

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.

Grading criteria:
criterion: Agent identifies Michael's top TableFind reservation spot as it appears in the live reservation counts (whichever restaurant has the highest count, or reports the tie if multiple are tied for top)
criterion: Agent identifies Cooper's Seafood House as Michael's top HangryDash delivery restaurant based on the live order history counts
criterion: Agent computes the overlap between the two top-5 lists explicitly
criterion: Agent explains Michael's dine-in vs delivery split in clear prose
criterion: Agent references the TableFind reservation counts and HangryDash delivery order counts it pulled when describing Michael's dine-out vs delivery split
criterion: Agent reports both top-5 dine-out reservations and top-5 delivery restaurants with the split percentage before finishing the answer
Task (medium, preference_inference / pattern_inference)
Primary app: multi_app
Apps involved: HangryDash

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.

Grading criteria:
criterion: Agent opens HangryDash and enumerates Michael's order history (multiple orders, not a single order)
criterion: Agent computes order frequency per restaurant or per cuisine from the history (not just lists raw orders)
criterion: Agent identifies Michael's actually-most-ordered HangryDash restaurants (top 2-3 by live order count), citing specific order counts per restaurant from the live data
criterion: Agent gives a clear preference verdict on whether Michael is actually sticking to his stated 'healthy lunch' (Sweetgreen) narrative, backed by the live order-count distribution — calling out any gap between the stated preference and actual behavior
Task (hard, preference_inference / pattern_inference)
Primary app: multi_app
Apps involved: BatBucks
OddsMarket

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.

Grading criteria:
criterion: Agent surfaces the GME BatBucks position with shares and cost basis
criterion: Agent surfaces the OddsMarket GameStop-above-$100 YES position
criterion: Agent explicitly uses cost basis only (not live prices)
criterion: Agent proposes a coherent rebalance that leans INTO the existing GME bias
criterion: Agent references the BatBucks GME shares cost basis and OddsMarket GameStop bet it pulled when proposing the lean-in rebalance for Michael's GME conviction
criterion: Agent reports a specific lean-INTO-GameStop rebalance using cost basis only before finishing the conviction-doubling proposal
Task (medium, retrieval / personal_lookup)
Primary app: multi_app
Apps involved: Cheskepdia
HooliMail
Files

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 — but the Cheskepdia booking is the source of truth.

Grading criteria:
criterion: Agent opens Cheskepdia and locates the Sandals Montego Bay booking
criterion: Agent reads off the Cheskepdia confirmation number for the Sandals Montego Bay Jamaica booking as shown live on the record
criterion: Agent searches HooliMail for any Sandals Jamaica reservation confirmation email (if no such email exists, agent says so rather than fabricating)
criterion: Agent opens the Jamaica trip planning doc (~/Documents/Trips/sandals_montego_bay_jamaica.txt) and corroborates the Sandals confirmation number against the Cheskepdia record for the concierge
Task (hard, retrieval / aggregation_reporting)
Primary app: multi_app
Apps involved: Gringotts
HooliMail

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 — but Gringotts is the primary source.

Grading criteria:
criterion: Agent lists the recurring auto-charges from Gringotts bill_pay as they appear live — the full set of monthly-frequency subscriptions seeded in the table
criterion: Agent reports each subscription's exact monthly amount as listed in Gringotts bill_pay
criterion: Agent lists the monthly recurring charges from the bill_pay table as they appear live (and optionally any separate credit card autopay or quarterly tax charges that aren't in bill_pay) without fabricating extra auto-charges
criterion: Agent opens HooliMail and cross-references for any subscription welcome or renewal confirmations against the Gringotts recurring auto-charges; if no such emails are present, explicitly notes the absence rather than fabricating matches
Task (hard, retrieval / personal_lookup)
Primary app: multi_app
Apps involved: Cheskepdia
Dinoco Airlines

Instruction: For my recent NYC trip, pull up the hotel confirmation, the flight confirmation, and the check-in date — I need to send them to someone. I stayed at the Greenwich and flew Dinoco.

Grading criteria:
criterion: Agent finds The Greenwich Hotel NYC booking in Cheskepdia and reports the live confirmation number as shown on the booking
criterion: Agent finds the NYC Dinoco flight in Dinoco Airlines and reports the seeded flight confirmation code from the live booking
criterion: Agent reports the NYC check-in date as seeded on the Greenwich Hotel booking
criterion: Agent reports the Greenwich hotel confirmation, the Dinoco flight confirmation, and the NYC check-in date together in one response for the recent NYC trip
Task (medium, retrieval / personal_lookup)
Primary app: multi_app
Apps involved: Cheskepdia

Instruction: What was the total cost of my Jamaica trip — 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.

Grading criteria:
criterion: Agent opens Cheskepdia and loads the upcoming Sandals Montego Bay (Jamaica) booking
criterion: Agent reports the trip total cost as it is shown on the live Cheskepdia Sandals Montego Bay booking
criterion: Agent reports the host name as listed on the live Cheskepdia Sandals Montego Bay booking (Sandals Resorts Concierge)
criterion: Agent reports the amenities list shown on the live Cheskepdia Sandals Montego Bay booking (or notes that no amenities are listed if the booking shows none)
Task (medium, retrieval / personal_lookup)
Primary app: multi_app
Apps involved: SpeedTax
Files

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.

Grading criteria:
criterion: Agent opens SpeedTax and locates the most-recent W-2 showing gross income and federal withholding fields
criterion: Agent reports the gross wages shown on the most-recent SpeedTax W-2 and Dunder Mifflin as the employer
criterion: Agent reports the federal withholding shown on the most-recent SpeedTax W-2 and cross-checks the value against w2_summary.txt
Task (hard, retrieval / personal_lookup)
Primary app: multi_app
Apps involved: SpeedTax
Files

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.

Grading criteria:
criterion: Agent opens SpeedTax and finds the most-recent 1099 entry showing the income amount and payer for the accountant summary
criterion: Agent reports the most-recent SpeedTax 1099 income amount from Scranton Improv Academy and the charitable-contribution total from the deductions section
criterion: Agent opens ~/Documents/Tax_2025/1099s.txt and cross-checks the 1099 income payer (Scranton Improv Academy) and amount against the SpeedTax value
criterion: Agent navigates to the most-recent SpeedTax return's deductions section and surfaces the charitable contributions line for the accountant summary
Task (hard, retrieval / personal_lookup)
Primary app: multi_app
Apps involved: Files

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.

Grading criteria:
criterion: Agent locates the Holly playlist text file anywhere on Michael's filesystem and reports the absolute path where it was found
criterion: Agent opens / reads the file (does not summarize from memory)
criterion: Agent lists the actual tracks that appear in the playlist file (not generic love songs)
criterion: Agent's response is grounded in the file content, not in fan-fiction guesses about what Michael would put on a Holly playlist
Task (hard, situated_action / bounded_action)
Primary app: multi_app
Apps involved: HooliMail
Files

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.)

Grading criteria:
criterion: Agent opens the team_morale_initiative_q2 doc and uses it to summarize the sign-off ask
criterion: Agent sends the HooliMail message to toby.flenderson@dundermifflin.com with a subject line referencing the Q2 Team Morale Initiative HR sign-off ask
criterion: Agent writes the Toby sign-off email in a short workplace tone without personal hostility or jabs at Toby
criterion: Agent sends a new outbound HooliMail from michael.scott@dundermifflin.com to toby.flenderson@dundermifflin.com requesting Q2 Team Morale sign-off
Task (medium, situated_action / bounded_action)
Primary app: multi_app
Apps involved: HooliWork
OddsMarket

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.

Grading criteria:
criterion: Agent opens OddsMarket and checks the NBC Office reboot/revival position before composing, reporting its current status (open or settled) rather than fabricating
criterion: DM is sent to Dwight Schrute (not posted to a public channel)
criterion: Agent's DM to Dwight references the Office reboot rumor and notes Michael's OddsMarket prediction-market stake
criterion: Agent opens HooliWork and starts or continues a direct message thread with Dwight Schrute before composing the Office reboot grapevine question
Task (hard, situated_action / bounded_action)
Primary app: multi_app
Apps involved: eTaxi
Dinoco Airlines
HooliCalendar

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.

Grading criteria:
criterion: Agent verifies the flight time 06:00 in Dinoco Airlines before booking
criterion: eTaxi pickup is scheduled for the live Jamaica departure date from Dinoco with at least 2.5h buffer before the flight
criterion: Pickup uses 1725 Slough Ave, Apt 4B and dropoff is AVP
criterion: HooliCalendar reminder event is created for the pickup
Task (medium, situated_action / bounded_action)
Primary app: multi_app
Apps involved: TableFind
HooliCalendar

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.

Grading criteria:
criterion: Agent books at Cotogna (the seeded Downtown Scranton Italian TableFind venue), not a different venue
criterion: Agent books the Cotogna reservation for party of 6 at 6:30pm on the next upcoming Wednesday date
criterion: Agent creates a matching HooliCalendar event block for the Cotogna reservation at 6:30pm so Michael does not forget
criterion: Agent confirms and reserves the Cotogna TableFind booking so a confirmation screen or confirmation number for the next-Wednesday 6:30pm party of 6 reservation appears
Task (hard, situated_action / multi_step_orchestration)
Primary app: multi_app
Apps involved: Cheskepdia
Dinoco Airlines
HooliCalendar
HooliChat

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.

Grading criteria:
criterion: Michael's Jamaica Dinoco flight is cancelled in the airline app (matching the seeded Dinoco Jamaica booking)
criterion: HooliCalendar Jamaica block (spanning the live Dinoco/Sandals trip window) is removed or marked cancelled
criterion: HooliChat DM is sent to Jim Halpert announcing the trip is cancelled
criterion: Agent opens Michael's Cheskepdia Sandals Montego Bay booking and sends a host message requesting a manual cancellation (Michael prefers the host-message path so the hotel knows the reason, even though Cheskepdia also supports self-cancel)
criterion: Agent completes all four cancellation legs end-to-end
Task (hard, situated_action / bounded_action)
Primary app: multi_app
Apps involved: HooliShop
Files

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).

Grading criteria:
criterion: Agent scans HooliShop order history for any prior trophy or award-style purchase, noting whether one exists or not (either outcome is acceptable)
criterion: Agent cross-references Dundies 2026 Categories doc for trophy count
criterion: Agent adds a trophy or award-style product (closest equivalent in the HooliShop catalog) to the cart with a quantity matching the number of Dundies 2026 categories
criterion: Agent places the HooliShop Dundie trophy order so a new order row appears matching the Dundies ceremony category count
Task (hard, situated_action / bounded_action)
Primary app: multi_app
Apps involved: Gringotts
HooliChat

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.

Grading criteria:
criterion: Agent sends a $100 Zelle transfer to Pam Beesly as the recipient, matching Michael's request for a hundred bucks to pay her back
criterion: Memo references paying Pam back / covering / owing her
criterion: Agent opens HooliChat and confirms Pam Beesly is on Michael's contacts before starting the $100 Zelle transfer in Gringotts
criterion: Agent opens Gringotts and starts a new Zelle transfer flow before entering Pam Beesly as the recipient and $100 as the amount
Task (hard, situated_action / bounded_action)
Primary app: multi_app
Apps involved: LockedIn
Files

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.

Grading criteria:
criterion: Post references the Dundies 2026 event explicitly
criterion: Agent writes the Dundies 2026 LockedIn post in a voice matching Michael's headline 'World's Best Boss | Regional Manager | Improv Comedian | Author of Somehow I Manage' persona
criterion: Agent pulled teaser detail from the Dundies 2026 Categories doc
criterion: Agent publishes the Dundies 2026 announcement post on LockedIn so it appears in Michael's LockedIn feed as a new published post
Task (hard, situated_action / bounded_action)
Primary app: multi_app
Apps involved: LockedIn
HooliWork

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 — but use your judgment per request. If none of them are Dunder Mifflin colleagues, that's a perfectly fine answer.

Grading criteria:
criterion: Agent navigates to the LockedIn invitations page
criterion: Agent triages each pending LockedIn invitation thoughtfully: accepts legitimate-looking requests (any Dunder Mifflin colleagues that appear, plus external senders with genuinely thoughtful non-spam messages) and leaves or declines obvious recruiter spam. Either zero or one-plus DM colleagues in the queue is acceptable — what matters is the per-request judgment.
criterion: Agent reports the triage outcome explicitly to Michael (count accepted, count left/declined, and explicitly states the count of Dunder Mifflin colleagues found in the pending queue — whether zero or more — so Michael knows the answer wasn't accidentally empty)
criterion: Agent inspects each pending LockedIn connection request's profile (sender name, headline, message body) to make a per-request judgment, rather than blanket-accepting or blanket-declining; cross-checks HooliWork if any sender claims to be a Dunder Mifflin colleague
Task (hard, situated_action / bounded_action)
Primary app: multi_app
Apps involved: OddsMarket

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) — pick from whatever the live markets list actually shows — 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.

Grading criteria:
criterion: Agent browses the OddsMarket markets list and selects 3 markets matching Michael's taste profile (Office/NBC reboot, Scranton/PA local, NBA, celebrity romance, or similarly on-brand markets)
criterion: Agent adds each of the 3 chosen markets to the OddsMarket watchlist via the watchlist add control (not by opening a position)
criterion: Agent verifies all 3 newly-added markets appear in the OddsMarket watchlist view after adding
criterion: Agent places zero new trades during the task — open-positions list and account balance are unchanged from the start of the session
Task (medium, situated_action / bounded_action)
Primary app: multi_app
Apps involved: HooliChat
Files

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.

Grading criteria:
criterion: Message is posted specifically to the 'Dundie Awards Planning' group (not Party Planning Committee or elsewhere)
criterion: Content reflects the categories from the Dundies 2026 Categories doc
criterion: Agent opens the Dundies 2026 Categories doc under ~/Documents to read the full category list before composing the HooliChat message
criterion: Agent sends the composed Dundies categories message into the HooliChat 'Dundie Awards Planning' group thread so it appears in the chat history
Task (hard, situated_action / bounded_action)
Primary app: multi_app
Apps involved: HooliChat
Cheskepdia

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.

Grading criteria:
criterion: Agent opens Cheskepdia and confirms the Sandals Montego Bay booking details for the Jamaica trip before sending the Holly DM
criterion: Agent's HooliChat DM to Holly states both the Jamaica check-in and check-out dates read live from the Cheskepdia Sandals Montego Bay booking
criterion: DM is sent to Holly Flax specifically, not a group
criterion: Agent's HooliChat DM to Holly Flax names the Sandals Montego Bay hotel that Michael booked alongside the Jamaica check-in and check-out dates
Task (hard, situated_action / bounded_action)
Primary app: multi_app
Apps involved: HooliMail
Files

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.

Grading criteria:
criterion: New HooliMail message is sent to pam.beesly@dundermifflin.com with the Dundies categories attached
criterion: Agent attaches the Dundies 2026 Categories doc to the HooliMail message addressed to Pam
criterion: Agent's HooliMail body to Pam asks her to proofread the attached Dundies 2026 Categories doc
criterion: Agent locates the Dundies 2026 Categories doc at ~/Documents/Dundies_2026_Categories.txt in Files before attaching it to the HooliMail message to Pam
Task (hard, situated_action / bounded_action)
Primary app: multi_app
Apps involved: HooliMail
Files

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.

Grading criteria:
criterion: Agent sends a new outbound reply mentioning Cooper's Seafood House from michael.scott@dundermifflin.com to every Dundies planning email it can find in the inbox (up to 5; whatever count exists is the correct answer)
criterion: Agent addresses each Cooper's Seafood House pitch reply to the actual sender of the planning thread it is replying to (different recipients per thread; if only 2 Dundies threads exist, 2 distinct recipients is the correct outcome)
criterion: Agent writes each Cooper's Seafood House pitch reply with tailored context per recipient instead of identical copy-paste body text
criterion: Agent opens the Dundies 2026 Categories doc to pull category context that informs the tailored Cooper's Seafood House pitch replies to the Dundies planning contacts
Task (hard, situated_action / bounded_action)
Primary app: multi_app
Apps involved: HooliMail
Gringotts
Files

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.

Grading criteria:
criterion: Agent verifies the Scranton Improv Academy vendor in Gringotts before composing, and reads ~/Downloads/Improv_Class_Certificate.txt (the canonical seeded source for the academy's contact email) to look up the recipient
criterion: Email references the Jamaica trip as the reason for needing a makeup class, with a date window tied to the trip the agent establishes
criterion: Email explicitly requests a make-up or rescheduled class
criterion: Agent sends a new outbound HooliMail message to a Scranton Improv Academy contact (e.g., scheduling@scrantonimprov.com, info@scrantonimprov.com) after TASK_START asking for a makeup class around Jamaica dates
Task (hard, situated_action / bounded_action)
Primary app: multi_app
Apps involved: HooliMail
Files

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.

Grading criteria:
criterion: Agent writes the HooliMail Jamaica out-of-office message template spanning the seeded Sandals Montego Bay live check-in/check-out dates read from the Jamaica trip doc
criterion: Agent's Jamaica out-of-office message states that urgent requests should go to Dwight Schrute at dwight.schrute@dundermifflin.com
criterion: Agent verifies dates against the Jamaica trip doc before composing
criterion: The OOO message is saved as a HooliMail draft so Michael can paste-as-reply or enable when leaving
criterion: Agent opens HooliMail and starts a new compose window for the Jamaica out-of-office template
Task (hard, long_horizon / multi_step_orchestration)
Primary app: multi_app
Apps involved: Gringotts
Files
LibreOffice
LockedIn
HangryDash
OddsMarket

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 — any 'investment' positions I've left open are basically a subscription to losing money.

Grading criteria:
criterion: Agent enumerates every recurring Gringotts bill_pay charge with payee, amount, and frequency
criterion: Agent cross-references each subscription against whichever usage source is most relevant (e.g., LockedIn post count for a Premium sub, Files for untouched media/storage, HangryDash orders for food-delivery) to identify the 3-4 worst offenders; if no matching usage source exists for a given subscription, explicitly notes the absence rather than forcing a match
criterion: Agent writes the kill-list memo in LibreOffice Writer naming the 3-4 most expensive subscriptions and saves it under ~/Documents
criterion: Agent posts a self-deprecating 'getting my financial act together' or 'financial discipline' update to LockedIn referencing the kill-list findings
criterion: Agent verifies the LockedIn post and saved kill-list memo both persist at the end of the task
criterion: Agent surfaces OddsMarket open positions as part of the subscription-style spend audit and notes them as cuttable if they're underwater
Task (hard, long_horizon / multi_step_orchestration)
Primary app: multi_app
Apps involved: Files
HooliMail
HooliWork
LibreOffice

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 — 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.

Grading criteria:
criterion: Agent uses Files (Nautilus) to survey the existing ~/Documents tree and identifies which loose files should go into Personal/ vs Work/
criterion: Agent creates ~/Documents/Personal/ and ~/Documents/Work/ folders (if missing) and moves loose files into them by topic
criterion: Agent opens HooliMail and archives messages older than 6 months from the inbox
criterion: Agent writes a one-page 'My new file/email system' memo in LibreOffice Writer and saves it under ~/Documents
criterion: Agent posts an 'inbox zero today' celebration message in the HooliWork #random channel
criterion: Agent confirms each artifact was created/moved (memo saved, files re-organized, messages archived, channel post visible) without requiring exact counts
criterion: Agent uses the Files (Nautilus) GUI (not just shell commands) for the visible file-tree reorganization so directory moves are observable in the file-manager UI
Task (hard, long_horizon / multi_step_orchestration)
Primary app: multi_app
Apps involved: Gringotts
HooliCalendar
HooliMail
Files
LibreOffice

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.

Grading criteria:
criterion: Agent pulls every Scranton Improv-related charge from Gringotts (the bi-weekly SCRANTON IMPROV ACADEMY subscription transactions as they appear live) with date and amount
criterion: Agent pulls every improv-related event from HooliCalendar with date and time
criterion: Agent pairs charges to calendar blocks and lists mismatches (charges with no block, blocks with no charge)
criterion: Agent composes and sends/drafts a HooliMail to a Scranton Improv Academy contact (any reasonable academy address) explaining the attendance gaps and asking about a make-up class
criterion: Agent writes the attendance reconciliation memo in LibreOffice Writer and saves it under ~/Documents
criterion: Agent verifies the email sent + memo file + reconciliation summary all persist
criterion: Agent reads ~/Downloads/Improv_Class_Certificate.txt for academy context (completion level, instructor comments) and references it in the email rather than fabricating academy details
Task (hard, long_horizon / multi_step_orchestration)
Primary app: multi_app
Apps involved: Cheskepdia
Dinoco Airlines
Gringotts
HooliCalendar
LibreOffice
Files
LockedIn

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.

Grading criteria:
criterion: Agent pulls The Greenwich Hotel booking total from Cheskepdia
criterion: Agent pulls the Dinoco NYC flight cost from the airline app
criterion: Agent cross-references Gringotts for related NYC trip charges in the Dinoco NYC flight window (the 3-4 day NYC block around the Dinoco booking)
criterion: Agent reads the HooliCalendar NYC trip block (the calendar events spanning the Dinoco NYC flight window) for trip context
criterion: Agent compiles the post-mortem write-up in LibreOffice Writer and saves it under ~/Documents/Trips/
criterion: Agent submits a 4-star Cheskepdia review for The Greenwich Hotel praising location and noting price
criterion: Agent posts a 'NYC trip recap' update to LockedIn
criterion: Agent verifies the saved post-mortem, the Cheskepdia review, and the LockedIn post all persist
Task (hard, long_horizon / multi_step_orchestration)
Primary app: multi_app
Apps involved: Files
LibreOffice
HooliWork
SprintBoard

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 — the file manager view is what makes it obvious what's actually in there.

Grading criteria:
criterion: Agent uses Files (Nautilus) to inventory ~/Documents files per subfolder with counts and total size
criterion: Agent pulls the SprintBoard project list (Team Morale Initiative Q2, Diversity Day Planning 2026, Movie Monday Program) with task counts
criterion: Agent composes a one-page IT inventory memo in LibreOffice Writer
criterion: Agent saves the memo to ~/Documents
criterion: Agent posts an 'IT inventory complete' message in HooliWork #random
criterion: Agent verifies the saved memo + the channel post both persist
criterion: Agent uses Files (Nautilus) to walk ~/Documents visually during the IT inventory pass (not just shell ls / cat)
Task (hard, long_horizon / multi_step_orchestration)
Primary app: multi_app
Apps involved: HooliMail
SpeedTax
Gringotts
LibreOffice Calc
HangryDash
TableFind
HooliShop
Files

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) — 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).

Grading criteria:
criterion: Agent opens the Jan rejection email thread in HooliMail and extracts the specific rejected line items with reasons
criterion: Agent reports, for each flagged item in Jan's rejection list, whether supporting evidence exists in the expected source-app category (TableFind/HangryDash for dining; HooliShop for purchased goods; eTaxi for ride spend) — approximate-amount or category-only matches are acceptable, and the agent does NOT need to find an exact-dollar match for the email's stated figures; the agent should explicitly note when only partial/approximate evidence is found
criterion: Agent cross-checks Gringotts for matching card charges that loosely correspond to the flagged items (any approximate or category-consistent match counts; exact-amount match not required)
criterion: Agent cross-checks the most-recent SpeedTax return's deductions to flag any rejected item that's already claimed (double-dip)
criterion: Agent composes the corrected resubmission in LibreOffice Calc with per-item explanations
criterion: Agent saves the resubmission to ~/Documents/Q1_expense_resubmit.ods
criterion: Agent opens HooliMail and drafts a reply to Jan with the resubmission summary, saved as a draft (not sent)
criterion: Agent confirms the draft, the saved doc, and the receipt-matching list all persist after the workflow ends
criterion: Agent rebuilds the corrected expense report as a LibreOffice Calc table (one row per line item with source app, amount, deduction-status columns) so Jan can audit it cleanly
Task (hard, long_horizon / multi_step_orchestration)
Primary app: multi_app
Apps involved: Cheskepdia
Gringotts
LockedIn
LibreOffice
Files
HooliMail
HooliChat

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.

Grading criteria:
criterion: Agent opens both Sandals Cheskepdia bookings (Sandals Montego Bay and Sandals Royal Barbados) and reads the live totals / dates / property names / confirmation numbers
criterion: Agent cross-checks Gringotts for the matching hotel charges on both Sandals bookings
criterion: Agent drafts 5-star reviews for both stays in LibreOffice Writer and saves under ~/Documents/Trips/
criterion: Agent either (a) saves both 5-star LibreOffice review drafts under ~/Documents/Trips/ AND submits both reviews on the Sandals Montego Bay and Royal Barbados Cheskepdia bookings, OR (b) saves both LibreOffice drafts AND composes both Cheskepdia reviews as drafts awaiting Michael's review before posting (honoring the 'first so I can edit before posting' instruction)
criterion: Agent emails Holly via HooliMail about writing the Sandals reviews
criterion: Agent DMs Pam in HooliChat with a 'somehow I managed' luxury Sandals message
criterion: Agent posts a 'luxury traveler era' update to LockedIn referencing the Sandals stays
criterion: Agent verifies both reviews + both messages + the LockedIn post all persist after refresh