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.

Agent computes the GameStop + Rivian cost-basis sum from the seeded holdings (GME shares × avg_cost + RIVN shares × avg_cost) and reports that consolidation pool figure

Agent reports the new total VTI position after the roll (existing VTI shares plus the additional shares funded by the GameStop+Rivian sell)

Presents a before/after portfolio composition with percentages showing how each position changes

Notes explicitly that the calculation uses cost basis (not market price) per the user's request

Agent lists Michael's current BatBucks holdings (live count from /api/holdings) with shares times avg_cost before computing the GameStop and Rivian sell pool

Agent divides the consolidation pool by VTI's avg_cost and reports the count of additional VTI shares to purchase from the GameStop+Rivian sell proceeds

Agent produces the before/after report in LibreOffice Calc (opens Calc, enters the portfolio data and percentages into a spreadsheet, and saves or presents the file)


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 — 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 — a reasonable approximation toward the 60/20/20 shape is the goal.

Agent reads all current BatBucks holdings (live count from /api/holdings) and records each ticker's avg_cost value at cost basis before placing any orders

Agent sells every GME share Michael holds (full position liquidation) in a single or combined order

Agent computes a VTI buy quantity that pushes VTI toward approximately 60% of the rebalanced blue-chip (VTI+SBUX+DIS) cost-basis total, treating the 60/20/20 target as an approximation (RIVN held out of the target bucket)

Agent places a VTI buy order for the computed quantity

Agent confirms new holdings row shows GME=0 and VTI shares increased

Agent explicitly uses cost-basis framing (not market value)

Agent verifies the GME sell order and VTI buy order persist in the BatBucks order history and that the holdings table reflects the rebalance with cash updated


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.

Agent opens BatBucks and lists all current holdings (live count from /api/holdings) with their avg_cost values to plan the stop-loss orders

Agent submits a Stop order (single stop price, not Stop-Limit) for every current BatBucks holding (live count from /api/holdings) at ~15% under each ticker's actual avg_cost (computed from holdings)

Agent creates a new BatBucks watchlist named 'Oscar's Picks'

Agent adds 8 big-name/mainstream ETF tickers (e.g., VTI, VOO, QQQ, SPY, DIA, IWM, VEA, VWO or comparable large-AUM broad-market ETFs) to the 'Oscar's Picks' watchlist in BatBucks

Agent reloads BatBucks and confirms stop-loss orders are accounted for (open or filled) for each current holding — noting that any stop placed below the current trading price may fill immediately — and the 'Oscar's Picks' watchlist persists after refresh


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/ — 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.

Agent pulls Michael's BatBucks RIVN holding (shares and avg_cost from the holdings view / /api/holdings) and reports it as the source of his RIVN exposure

Agent reports Michael's RIVN cost-basis dollar exposure (shares × avg_cost from live BatBucks holdings) and expresses RIVN's share as a percent of the total cost-basis portfolio

Agent frames the analysis using cost basis (avg_cost) per the user's request, not market value

Agent proposes a RIVN trim plan consistent with Michael's historical consumer-brand bias (preserves DIS/SBUX-style narrative names rather than suggesting a pure-index dump)

Agent reports the BatBucks holdings rows as the data source for the trim recommendation instead of inventing numbers

Agent delivers the full RIVN trim answer including cost-basis concentration percent and recommendation without abandoning the task midway

Agent opens ~/Downloads/WUPHF_Investment_Agreement.txt and references it as the founding 'bad bet' pattern that explains the current RIVN over-exposure

Agent produces the portfolio review in a LibreOffice Writer document, as requested in the instruction


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?

Agent reports Michael's BatBucks portfolio value at cost basis (sum of shares × avg_cost across all current holdings, live count from /api/holdings)

Agent reports the cash balance in the BatBucks account separately from holdings value

Agent uses cost basis (avg_cost) framing as the user requested, not market value

Agent reconciles the reported BatBucks cost-basis total and cash balance against the holdings table rows instead of fabricating numbers


Instruction: Trim my GameStop position in half and roll the proceeds into VTI. I'm trying to be less of a degenerate about this.

Agent sells approximately half of the live GME position (roughly half the seeded share count, rounding up or down by one share) as the half-position trim into VTI

Agent buys VTI using proceeds from the GME sale (not cash from elsewhere)

Agent confirms both GameStop sell and VTI buy orders executed and verifies the updated BatBucks positions reflect the half-GME trim rebalance

Agent opens BatBucks and reports the existing GameStop GME position share count (read from the live holdings table) before executing the half-trim sell into VTI


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?

Agent lists all four Cheskepdia trip bookings with their property names (Jamaica, NYC, Barbados, Philadelphia hotels)

Agent categorizes each of the 4 Cheskepdia hotel bookings as luxury-tier or budget-tier and labels which group the pattern favors

Agent flags Sandals (Montego Bay + Royal Barbados) as the dominant luxury pattern

Agent identifies the Philadelphia Radisson booking from the four hotel trips as the business-travel outlier among Michael's luxury-hotels pattern

Agent lists specific Cheskepdia booking rows (property name, total) from the four trips when stating the luxury-versus-budget verdict

Agent delivers the full luxury-versus-budget guy verdict with the pattern summary, not stopping before answering the four-trip question


Instruction: I'm feeling nostalgic. Book me an upcoming Scranton weekend, Friday through Sunday. Pick a well-rated property in town and book it.

Agent books a Scranton property on Cheskepdia with a future check-in date for the nostalgic weekend trip

Agent's booked Scranton stay spans Friday check-in through Sunday check-out as requested for the upcoming weekend

Agent browses the Cheskepdia Scranton search results and picks a well-rated property before booking

Agent confirms the new Cheskepdia Scranton booking details (property, Friday-to-Sunday dates, total) after submitting the reservation for the nostalgic weekend


Instruction: Open the Dinoco Airlines app, check in my next upcoming flight and confirm that the boarding pass screen actually renders. Download it locally as well.

Agent opens Dinoco Airlines and locates the next upcoming (non-cancelled) flight by departure_date in the live booking list

Agent clicks the 'Check in' control on that upcoming flight's row, not on a past or cancelled flight

Agent verifies that the boarding pass view actually renders after check-in (flight number, route, and seat/gate details visible)

Agent downloads the boarding pass locally (e.g., saves the file to disk or confirms a download action was triggered)

Agent reports the boarding pass details (flight number and route) it observed on the rendered pass


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.

Agent filters Dinoco flight history to flights that are completed (not cancelled and not still-upcoming) within the past 12 months and sums their miles from the live flight history

Agent also lists upcoming Dinoco flights and their mileage alongside the completed-flight data, as explicitly requested

Agent produces a per-trip table or spreadsheet-style breakdown with each trip and its miles, ending with a cumulative total row

Agent reports the count of completed Dinoco flights in the past 12 months and the total miles for that window (even 1-2 flights is a valid result)

Agent delivers a single answer covering completed-flight totals, upcoming-flight mileage, and the per-trip breakdown together


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?

Agent creates a new one-way Dinoco booking with origin AVP and destination JFK in the Economy fare class for next Friday

Agent selects an evening or night departure flight (departure time in the evening or after sunset) and picks a seat on the left side of the aircraft

Agent pays with Michael's MasterCard (not a different saved card or a new card entry)

Agent completes the booking and captures the new Dinoco confirmation number returned by the app

Agent confirms a booking confirmation email was received and pulls it up as requested by Michael

Agent delivers a single end-to-end answer: new confirmation number plus confirmation that the booking email was found


Instruction: What's my current FlyMiles loyalty tier on Dinoco and how many miles do I have in the bank?

Agent reads Michael's FlyMiles loyalty tier directly from the live Dinoco profile (not inferred from email or other apps)

Agent reads Michael's current FlyMiles miles balance directly from the live Dinoco profile

Agent reports the loyalty tier and miles balance together in a single answer


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.

Agent picks the next upcoming Dinoco booking that is still cancellable (not already past or cancelled) and cancels it through the Dinoco UI

Agent confirms the cancellation confirmation email was received and pulls it up as requested

Agent verifies a new travel-credit entry posts in Dinoco for the cancelled fare and reports the credit amount received

Agent explicitly reports what flight was cancelled (route and/or flight number) and how much credit was received

Agent delivers a single end-to-end answer: cancelled booking details, cancellation email confirmation, and travel-credit amount


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.

Agent filters eTaxi to rides whose dropoff_address starts with 'Dunder Mifflin' (the unique-to-Office prefix that disambiguates the office from any home rides on the same street)

Agent sums those rides to a YTD commute spend number

Agent reports the Dunder Mifflin eTaxi commute ride count alongside the current-year YTD commute-only spend total

Agent answers the how-much-spent question for Dunder Mifflin eTaxi commute rides with a single YTD dollar figure for the current year


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 — if it already matches, no action needed; if it's wrong or missing, fix it and save the change.

Agent opened eTaxi and actually looked at the saved work/office location entry (whichever label the app uses — 'Work' or 'Office')

Agent reported the current saved work/office address to Michael, explicitly confirming whether it matches Dunder Mifflin at 1725 Slough Ave (with or without Suite 200 / Scranton, PA suffix)

Agent explicitly states whether the saved work/office address already matches '1725 Slough Ave' (in which case no action is needed) or required a correction, and applies the update only if a mismatch was found

If the agent applied any correction, it explicitly saves/commits the updated work/office location entry so the change persists (not just a temporary edit); if no correction was needed, the agent explicitly says so and does not modify the entry

Agent navigates into the eTaxi saved locations screen and inspects the existing work/office entry (labeled 'Work' or 'Office' in the app) before deciding whether to update it to Dunder Mifflin 1725 Slough Ave


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.

Agent locates the Threat_Level_Midnight_Sequel_Notes.txt file in ~/Documents/Projects and reports its absolute path

Agent reads the file and provides a quick rundown of the plot, cast, and other elements from the sequel notes

Agent produces a draft script grounded in the sequel notes (not a generic action script) that uses the notes as a starting point

Agent's draft script includes multiple Dunder Mifflin coworkers as named characters (casting reason requirement)

Agent opens the Files app and navigates to ~/Documents/Projects to locate the file before summarizing or drafting


Files
LibreOffice Impress
HooliWork
HooliMail

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.

Agent locates Dundies_2026_Categories.txt in ~/Documents, reports its absolute path, and enumerates the Dundies 2026 categories from the document

Agent creates a LibreOffice Impress presentation (.odp or .pptx) that includes the Dundies categories as slide content

Agent sends messages (via HooliWork, HooliMail, or BuzzChat) to the Dundies candidates found in the document asking them to show up to the Dundies

Agent opens the Dundies_2026_Categories.txt doc in the Files app and reads its content before producing the presentation or messages


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.

Agent locates Somehow_I_Manage_Chapter_1.txt in ~/Documents and reports its absolute path

Agent provides a faithful, coherent summary of Chapter 1's content in Michael's voice and tone

Agent writes two additional chapters (Chapter 2 and Chapter 3, or equivalent) that continue the 'Somehow I Manage' book in Michael Scott's boss-lore style

Agent opens or creates a LibreOffice Writer document (.odt or .docx) to write the two new chapter extensions

Agent's chapter extensions maintain Michael's over-the-top, self-aggrandizing management-wisdom tone consistent with Chapter 1


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.

Agent locates and opens the existing Threat Level Midnight sequel notes file at ~/Documents/Projects/Threat_Level_Midnight_Sequel_Notes.txt via the Files app before adding new plot points

Agent adds at least 5 new plot points to the existing file and saves it so the additions persist on disk

Agent writes the 5 new plot points in Michael Scarn's Threat Level Midnight sequel tone (over-the-top action voice, big dramatic beats)

Agent sends the revised plot notes (or a summary/link) to at least a handful of Dunder Mifflin coworkers via HooliWork, HooliMail, or BuzzChat as potential casting candidates

Agent addresses the outreach to coworkers explicitly as potential casting candidates for the Threat Level Midnight sequel


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%.

Agent picks a salad-forward HangryDash restaurant from Michael's live order history (e.g. Sweetgreen or a comparable salad/bowl-focused restaurant Michael has ordered from before)

Agent picks a lunch within Michael's usual HangryDash lunch spending range that matches his salad/bowl dietary pattern

Agent attempts to apply a HangryDash promo code at checkout for the salad-forward lunch order, or notes that no promo code is available if none surface

Agent enters a 20% driver tip on the salad-forward HangryDash lunch order at checkout

Agent places the order and sees it in history

Agent reviews HangryDash order history to confirm the chosen restaurant is salad-forward and one Michael has ordered from before

Agent reviews HangryDash order history highlights to identify a salad-forward restaurant Michael has ordered from before picking the lunch order target

Agent adds the picked salad-forward lunch item (priced within Michael's usual HangryDash budget) from the chosen salad-forward restaurant into the cart before proceeding to checkout


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.

Agent opens HangryDash and navigates to the order history screen to surface the prior Cooper's Seafood House order list

Agent locates your most recent Cooper's Seafood House order in history

Agent clicks the Reorder button on the prior Cooper's Seafood House entry or opens a fresh HangryDash Cooper's Seafood House order seeded with the same line items

Agent adds the exact same item(s) from Michael's most recent Cooper's Seafood House order (as shown in his HangryDash order history) into the new cart

Agent adds an order note requesting extra napkins and crackers on the side and that hot items be sent piping hot

Agent attempts to apply a HangryDash promo code at checkout for the Cooper's Seafood House reorder, or notes that no promo code is available if none surface

Agent enters a 20% driver tip on the Cooper's Seafood House HangryDash reorder before submitting

Agent places the order and verifies it in history


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.

Agent queries tip_amount and subtotal at the order-level for the HangryDash food-delivery tip analysis, covering Michael's full order history

Agent computes mean tip in both $ and % terms

Agent identifies the modal tip percent (15%, 18%, 20%, or custom) from the HangryDash order history

Agent recommends a defensible pre-fill default tip value grounded in the observed HangryDash tip pattern

Agent creates a LibreOffice Calc spreadsheet (.ods or .xlsx) containing a per-order row report with at minimum the order identifier, tip amount, and subtotal columns for Michael's HangryDash order history

Agent cites the HangryDash order-history tip rows as the data source for the recommended smart-default tip value, not inventing numbers

Agent delivers the full food-delivery tip answer in dollars and percent plus the smart-default recommendation and the LibreOffice spreadsheet


Instruction: Order me my usual from Chili's — 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.

Agent identifies Chili's as the target restaurant and opens HangryDash order history to find Michael's prior Chili's orders

Agent places a Chili's order whose item(s) match Michael's most-frequent/modal item in his HangryDash Chili's order history (if two items tie for modal, either tied item is acceptable; matching the most-recent Chili's order is also acceptable as a tiebreaker)

Agent selects a delivery address on the order that matches Michael's saved home/primary HangryDash address

Agent adds the usual Chili's item(s) to the HangryDash cart and submits the order through the checkout flow so the order is placed


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.

Agent opens HooliCalendar and navigates to the Thursday day view to surface the scheduling conflict

Agent identifies any improv class event on the upcoming Thursday from live HooliCalendar (Scranton Improv Workshop, Improv Class, or any improv-tagged event) as the unmovable anchor

Agent checks the Thursday work meetings against the improv class window and either identifies an overlapping meeting or explicitly reports that no Thursday meeting conflicts with the improv block

If a conflict was found, agent picks a non-conflicting Thursday time slot for that meeting that does not touch the improv window (or states that no move is needed if no conflict was found)

If a conflict was found, agent moves the conflicting Thursday meeting in HooliCalendar to the new non-conflicting slot (or notes that no meeting needed to be moved)

If a meeting was moved, agent protects a 15-minute transition buffer immediately before the rescheduled Thursday meeting (either by creating a buffer event or by scheduling the meeting so at least 15 minutes of empty time precedes it)

If a meeting was moved, agent protects a 15-minute transition buffer immediately after the rescheduled Thursday meeting (either by creating a buffer event or by scheduling the meeting so at least 15 minutes of empty time follows it)

If a meeting was moved, agent sends updated HooliCalendar invites to the meeting attendees (Andy and Jim) after the move — OR, if the moved meeting has no attendees listed, agent explicitly notes that no attendees existed so no invites were needed

If a meeting was moved, agent messages Andy and Jim on HooliWork to notify them of the schedule change — OR notes that no HooliWork message was needed because no conflict existed or no move occurred

Agent verifies the Thursday view in HooliCalendar — confirming either that the moved meeting and improv class show no overlap, or that no conflict existed to resolve


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.

Agent opens HooliCalendar and switches to a 2-week view to plan the Dundies prep schedule

Agent creates the 'Dundies categories brainstorm' event in HooliCalendar early in week 1 of the prep schedule

Agent creates the 'Venue walkthrough' event in HooliCalendar mid-week 1 for the Dundies prep schedule

Agent creates the 'MC rehearsal' practice event late in week 1 of the HooliCalendar Dundies plan to lock in stage time

Agent creates the 'Catering confirmation' event in HooliCalendar early in week 2 for the Dundies prep schedule

Agent books the 'Dress rehearsal' final run-through near week 2's end on HooliCalendar so the Dundies cast walks the show before opening night

Agent selects a single shared Dundies color on each of the 5 prep events so they pop in the 2-week calendar view

Agent adds Pam, Dwight, Kevin, Jim, and Holly as attendees on each of the 5 Dundies prep events, or notes clearly that HooliCalendar's event editor does not expose an attendees picker and records the intended invitee list in the event body / description so Michael can follow up

Agent attempts to add 24-hour and 1-hour reminders on each of the 5 Dundies prep events if the HooliCalendar event editor exposes per-event reminders

Agent verifies all 5 Dundies prep events appear in the HooliCalendar 2-week view with the shared color and the five attendees


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.

Agent reads HooliCalendar visually (cua) for the current week to gather the AM vs PM event data

Agent counts AM vs PM events per day with numeric totals drawn from the live HooliCalendar week view

Agent computes and reports the week's AM:PM event ratio as a concrete numeric comparison

Agent calls out any conspicuous recurring morning or evening blocks on Michael's HooliCalendar week (e.g., a daily morning standup, a recurring evening prep block)

Agent states an explicit morning-heavy vs evening-heavy verdict on Michael's calendar for the current week

Agent saves the AM-vs-PM calendar analysis (per-day counts and final verdict) in a LibreOffice Writer document (.odt or .docx), as explicitly requested

Agent reports AM vs PM event counts that reflect what is actually visible in the HooliCalendar week view rather than invented totals

Agent finishes the AM-vs-PM calendar analysis and delivers both the per-day counts and the final morning-vs-evening verdict in the LibreOffice Writer note


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 — 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.

Agent posts a recap message in HooliChat Party Planning Committee that summarizes the conversation (quoting or summarizing the 3 most useful recent messages if there are enough, otherwise summarizing the entire conversation)

Agent posts a recap message in HooliChat Dundie Awards Planning that summarizes the conversation (quoting or summarizing the 3 most useful recent messages if there are enough, otherwise summarizing the entire conversation)

Agent posts a recap message in HooliChat Finer Things Club that summarizes the conversation (quoting or summarizing the 3 most useful recent messages if there are enough, otherwise summarizing the entire conversation)

Agent posts a separate status-update reminder in Party Planning Committee asking for any new agenda items

Agent's recap messages persist in their respective HooliChat groups after refresh (4 new messages total visible in chat history)

Agent opens HooliChat and enters each of the three groups (Party Planning Committee, Dundie Awards Planning, Finer Things Club) before composing the recap messages


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.

Agent pulls paired timestamps of incoming DMs and Michael's replies from HooliChat DMs to compute how fast he writes back

Agent groups the reply latencies into the <5min, <1h, <1d, and >1d buckets requested in the write-back prompt and reports a count per bucket

Agent calls out the mode bucket and characterizes Michael's response speed

Agent states a fast-responder vs ghoster verdict in plain English based on which reply-latency bucket dominates

Agent derives the write-back latency buckets from HooliChat DM timestamps and shows the per-bucket reply counts instead of stating the fast-responder verdict with no supporting data

Agent finishes the fast-vs-ghoster DM analysis and reports both the bucket counts and the final responder verdict


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.

Agent opens or starts a HooliChat DM thread with Jim Halpert before composing the Finer Things Club invite

Agent picks a reasonable near-future evening (this week or next) as the proposed Finer Things Club meetup time

Agent sends the DM to Jim Halpert as a one-on-one HooliChat message rather than posting it in a group channel

Agent writes a HooliChat DM body that proposes the chosen near-future evening to Jim and references the Finer Things Club meetup


Instruction: Triage my inbox. It's overflowing, so give me a per-sender count and the top 10 senders filling it up.

Agent reads Michael's HooliMail inbox messages — via the HooliMail app/API listing the Inbox folder including any sub-folders (Work, Travel, Receipts, etc.), OR by walking the Maildir filesystem at ~/Maildir/cur, ~/Maildir/new, and sub-folder cur/new dirs — but excludes the Sent folder and excludes Michael's own From: lines when counting senders

Agent groups the inbox messages by sender email and counts how many messages each sender is filling it up with

Agent reports the inbox senders as a top-10 ranked list with per-sender counts

Agent presents the top-10 inbox senders as a readable ranked list with one sender per line and a visible count column

Agent lists approximately 10 inbox sender entries in the top-senders ranking (not just 5 or 7)


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.

Agent opens HooliMail and clicks Write to open a new compose window addressed to pam.beesly@dundermifflin.com

Agent fills a non-empty subject line (e.g. 'Quick note') in the HooliMail compose window

Agent writes a short message body in the new HooliMail draft to Pam

Agent appends the 'World's Best Boss, Somehow I Manage' signature line at the end of the email body before saving

Agent saves the email to Pam as a draft in HooliMail (does not hit Send) so Michael can review later

Agent's draft persists in the HooliMail Drafts folder after saving and the signature line is visible in the saved draft body


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.

Agent locates Michael's sent emails to build the auto-triage data set — either by walking the Maildir filesystem (.Sent/cur or .Sent/new with 'From: michael.scott' grep) or by querying the HooliMail Sent folder via /api/emails?folder=sent

Agent computes a median reply latency per top sender from the paired received/sent timestamps and surfaces which senders Michael lets sit for days

Agent identifies the fastest-reply and slowest-reply senders with supporting evidence

Agent proposes a concrete auto-triage filter rule based on the data

Agent derives the fast-vs-days reply pattern from Maildir timestamps rather than guessing, and names Michael as the sender of record

Agent finishes the auto-triage build: the recommended priority filter rule is stated and references the fastest and slowest senders


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.

Agent reads ~/Downloads/DunderMifflin_Q2_Sales_Forecast.txt to extract the sales figures that ground the email body

Agent performs sales analysis in LibreOffice Calc using figures from the forecast file, producing a spreadsheet with empirical analysis (totals, trends, or comparisons) as an attachment or saved file for Michael to send along

Agent saves the most-recent-quarter sales summary email to David Wallace as a HooliMail draft and does not send it, so Michael can review it first

Draft is addressed to david.wallace@dundermifflin.com and the body references the most recent quarter's sales grounded in figures from the forecast file

Agent explicitly notes that it did not hit Send, leaving the HooliMail draft for Michael to review before sending


Instruction: Remember my most recent World's Best Boss Mug order from HooliShop? Pull up that order and start a return on it — 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.

Agent opens HooliShop and navigates to the order history view

Agent locates the most-recent World's Best Boss Mug order (any variant) in HooliShop order history

Agent submits a return request on 1 unit of the most-recent HooliShop World's Best Boss Mug order (any variant) via the order-actions Return button

Agent confirms the HooliShop return submission and the order's status reflects the return action

Agent reorders 1 World's Best Boss Mug on HooliShop (using the same prior product if available, or the closest equivalent in the catalog if the original SKU is no longer listed)

Agent reorders a Prime-eligible World's Best Boss Mug listing (HooliShop shows a PrimeBadge on fast-shipping items; picking a Prime-eligible product satisfies 'fastest shipping' since HooliShop has no separate speed selector)

Agent places the HooliShop reorder so the replacement World's Best Boss Mug enters order history

Agent posts a 5-star HooliShop product review with a short praising note on the World's Best Boss Mug product page (reviews on HooliShop are per-product via /api/products/[id]/reviews, not per-order)


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.

Agent searches HooliShop and finds the World's Best Boss mug listing matching the variant Michael has bought before

Agent enters a bulk HooliShop cart quantity of about 24 World's Best Boss mugs for the whole team

Agent checks the unit price and the HooliShop cart total before proceeding to the bulk-discount step

Agent applies a subscribe-save / bulk discount if surfaced at HooliShop checkout

Agent updates the HooliShop ship-to to the Dunder Mifflin office at 1725 Slough Ave so the bulk mug order ships to the office (entering a custom office ship-to at checkout is acceptable since HooliShop's saved addresses may not include a pre-labeled Work entry)

Agent places the HooliShop bulk World's Best Boss mug order and confirms it appears in Michael's order history

Agent's cart at checkout contains only World's Best Boss mugs (about 24 units) and no other products — the instruction explicitly says 'Don't buy anything else'

Agent reviews the final HooliShop bulk mug cart total at the checkout screen before submitting the order to the office address


Instruction: I want another copy of my own book — Somehow I Manage. Order me one, same as my last order of that book, and ship it home.

Agent opens HooliShop and searches for the 'Somehow I Manage' book listing (Michael's self-published leadership book) to surface the matching product page

Agent opens HooliShop order history and confirms a prior 'Somehow I Manage' book order (specifically the self-published Leadership Book, not the binding kit variant) before reordering — the most-recent leadership-book order suffices

Agent places a HooliShop order that contains exactly one 'Somehow I Manage' book matching the variant Michael previously bought

Agent selects Michael's saved home/primary address on HooliShop as the shipping address for the replacement book (the address labeled 'home' in his saved addresses)


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.

Agent ensures the HooliWork #sales channel notification_pref is set to 'all' via the channel preferences panel (flipping it if it is not already 'all', or verifying + keeping it at 'all' if it already is)

Agent ensures the HooliWork #general channel notification_pref is set to 'all' via the channel preferences panel (flipping it if it is not already 'all', or verifying + keeping it at 'all' if it already is)

Agent ensures the HooliWork #random channel notification_pref is set to 'all' via the channel preferences panel (flipping it if it is not already 'all', or verifying + keeping it at 'all' if it already is)

Agent ensures the HooliWork #party-planning-committee channel notification_pref is set to 'all' via the channel preferences panel (flipping it if it is not already 'all', or verifying + keeping it at 'all' if it already is)

Agent saves at least 10 important HooliWork messages as bookmarks spread across the #sales, #general, #random, and #party-planning-committee channels

Agent creates a new HooliWork thread in #random titled or about Pretzel Day

Agent posts an on-topic opening message in the new Pretzel Day thread in #random that mentions Pretzel Day rather than placeholder text

Agent verifies the notification-pref changes on the 4 channels, the 10 bookmarks, and the Pretzel Day thread all persist after a refresh


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.

Agent posts to the HooliWork #random channel (not another channel)

Agent writes the #random Monday post in Michael Scott's World's Best Boss motivational voice to kick the team's week off

Message explicitly frames the post as a Monday motivation (week kickoff, start the week strong, Motivational Monday, etc.)

Agent writes the #random Motivational Monday post as over-the-top self-aggrandizing World's Best Boss Michael Scott energy, not corporate HR boilerplate

Agent reads ~/Documents/Motivational_Quotes_Collection.txt and pulls at least one quote into the Motivational Monday post (or directly cites the file as the source)


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.

Agent navigates to the HooliWork #party-planning-committee channel before composing the Pretzel Day countdown message

Agent composes a Pretzel Day countdown message body that mentions Pretzel Day and includes hype language (days remaining, excitement, etc.)

Agent attempts to schedule or post the Pretzel Day countdown message for next Monday at 8:00 AM EST (scheduled delivery or immediate post with the specified time noted)

Agent posts or schedules the Pretzel Day countdown message in the HooliWork #party-planning-committee channel rather than another channel


Instruction: Reorder my last run from a Kwik-E-Mart store I've used recently — 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.

Agent opens Kwik-E-Mart and navigates to the order history view to surface a prior run at one of Michael's top-frequency stores or his most-recent store

Agent picks a reorder anchor at one of Michael's top-frequency Kwik-E-Mart stores by order count (any store tied at the top by order count is acceptable) OR his most-recent Kwik-E-Mart order, and bases the reorder on that order's line items

Agent starts a reorder and handles out-of-stock items appropriately — picks substitutions if any items are flagged OOS, or notes that all original items were available and proceeds without substitutions

Agent opens a second store and compares prices

Agent completes the price comparison and proceeds with the cheaper option (returns to the original store's cart if it is cheapest, or switches to the cheaper store)

Agent selects the earliest available delivery slot at Kwik-E-Mart checkout for the chosen-store reorder

Agent places the Kwik-E-Mart reorder and verifies it appears in the recent-orders history after checkout


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.

Agent opens Kwik-E-Mart, selects Wegman's as the store for the Dundies catering bulk order (instruction explicitly specifies Wegman's), and views any existing shopping lists before building the new catering list

Agent creates or extends a Dundies Catering shopping list (or a 'Party Supplies' list) in Kwik-E-Mart for the catering items

Agent adds 6+ Kwik-E-Mart shopping list categories (drinks, chips, plates, plastic silverware, napkins, ice) with quantities scaled for 100 people

Agent moves the Dundies Catering Kwik-E-Mart shopping list contents into the cart

Agent confirms delivery address is 1725 Slough Ave (Michael's home address) at Kwik-E-Mart checkout

Agent picks a delivery window at least 2 hours wide at Kwik-E-Mart checkout so Michael is not waiting all afternoon

Agent places the Kwik-E-Mart Dundies catering order and confirms the order total and delivery window persist in order history

Agent verifies the Dundies Catering shopping list persists and displays in Kwik-E-Mart shopping_lists after checkout


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.

Agent identifies Michael's favorite Kwik-E-Mart grocery store as the top-by-order-count store from live order history (/api/orders), naming whichever store has the plurality of orders

Agent reports the live order counts per store from Michael's Kwik-E-Mart order history (/api/orders), confirming the top-by-order-count store is ranked first ahead of the other stores Michael has used

Agent characterizes the typical line items Michael buys there

Agent writes a one-paragraph profile of Michael's Kwik-E-Mart grocery shopping habits at his favorite store

Agent reads Kwik-E-Mart order-history line items and states them as the data source backing the favorite grocery store ranking and buying profile

Agent delivers the favorite Kwik-E-Mart grocery store ranking and the buying-habits profile before ending the task


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!

Agent opens Kwik-E-Mart and locates Michael's most-recent Price Chopper order in the order history (filtering by store and picking the most recent Price Chopper basket as the anchor)

Agent copies the line items from that Price Chopper order into the new reorder cart at Price Chopper (not Wegmans or another store)

Agent adds oat milk to the cart if it was not already in the Price Chopper reorder, and adds eggs if they were not already in the Price Chopper reorder, per Michael's explicit request

Agent sets a 20% tip on the Kwik-E-Mart Price Chopper order at checkout

Agent selects Michael's home address (1725 Slough Ave, Apt 4B) as the Kwik-E-Mart delivery destination and submits the Price Chopper reorder checkout


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.

Agent opens LibreOffice Writer before loading the Dundies 2026 categories document for the bold and append edits

Agent opens the Dundies_2026_Categories.txt file in LibreOffice Writer (not a terminal editor)

Agent finds the 'Whitest Sneakers' line in the Dundies 2026 categories doc and selects it before applying formatting

Agent applies bold formatting to the 'Whitest Sneakers' line during the editing session via Ctrl+B or the toolbar bold button (visible in screenshots; bold attribute will not persist when the .txt source file is saved back as plain text — accept screenshot evidence of the formatting being applied at any point in the session)

Agent inserts a new 'Fine Work Outfit' category line immediately after the 'Whitest Sneakers' line in the Dundies 2026 categories doc

Agent saves the edited Dundies_2026_Categories.txt file back to the same ~/Documents path in Writer, keeping the original text format if prompted


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.

Agent reads ~/Documents/Dundies_2026_Categories.txt to retrieve this year's Dundies category names for the invitation

Agent opens LibreOffice Writer and creates a new document for the Dundies 2026 invitation

Agent writes a big bold centered top-of-page title reading 'THE DUNDIES 2026' in the Writer invitation document

Agent writes a short Dundies 2026 invitation intro paragraph below the title in the Writer document

Agent inserts a bulleted list of this year's Dundies categories pulled from Dundies_2026_Categories.txt into the Writer invitation document

Agent adds a signature block reading 'Michael Scott, World's Best Boss' at the bottom of the Writer invitation document

Agent saves the Dundies 2026 invitation as ~/Desktop/dundies_invite.odt fitting on a single page


LibreOffice Impress
Dinoco Airlines
Cheskepdia
HooliMail

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.

Agent creates an Impress deck for Michael's Jamaica trip that contains exactly 3 slides (flight, hotel, daily schedule)

Agent writes the Jamaica trip flight slide showing the flight number, departure time, confirmation code, and fare, all pulled from Michael's live Dinoco and/or HooliMail Jamaica trip sources (not invented)

Agent writes the Sandals hotel slide showing Sandals Montego Bay, the live Cheskepdia confirmation number, the live check-in and check-out dates, and the live total price — all read from Michael's Cheskepdia booking

Agent writes the third Jamaica trip slide as a rough day-by-day schedule spanning the live Sandals Montego Bay check-in/check-out window

Agent saves the three-slide Jamaica trip Impress deck to ~/Documents/Trips/jamaica_itinerary.odp inside Michael's Trips documents folder


HooliMail HooliCalendar HooliChat HooliWork Gringotts

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.

Agent surfaces important or unread HooliMail messages from the current week using 'from sender' or 'this week' framing (heuristic priority flagging by sender/subject is acceptable when no explicit priority/star flag is set)

Agent enumerates today's HooliCalendar events by reading the UI

Agent checks HooliChat and HooliWork for overnight messages and summarizes them

Agent reviews Gringotts for transactions posted since today's midnight

Agent delivers a consolidated morning brief that covers HooliMail priority email, HooliCalendar events, HooliChat/HooliWork overnight messages, and Gringotts charges

Agent organizes the morning brief so the four sources (email, calendar, overnight HooliChat/HooliWork, Gringotts card charges) are each clearly distinguishable and scannable

Agent includes all four morning-brief sources (HooliMail, HooliCalendar, HooliChat/HooliWork, Gringotts charges) before ending the task


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.

Agent opens Cheskepdia and reads the live Philadelphia overnight hotel booking (property name as shown on the Cheskepdia booking record), reporting its total price and dates as shown live

Agent cross-references Gringotts around the Philadelphia overnight trip dates (as read from the Cheskepdia booking) for related card charges such as the hotel (the hotel charge on the card may appear under a different merchant name — e.g. Hilton Garden Inn — than the Cheskepdia booking property, and may post on or shortly after the checkout date), gas, or food

Agent reports the combined Philadelphia trip total (hotel + any on-trip card charges) as the all-in damage Michael asked for

Agent states the Philadelphia trip all-in damage as a single final dollar figure combining the hotel and incidentals (not assuming a flight)


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.

Agent reads the Sandals Royal Barbados hotel booking total from Cheskepdia to add up Michael's committed Barbados trip spend

Agent locates Michael's Barbados flight booking on Dinoco Airlines and notes its confirmation code

Agent identifies the Dinoco Airlines Barbados flight charge in Gringotts (matching by confirmation code DN-78558 or the AVP->BGI route) as a charge that has posted to the account

Agent identifies the Cheskepdia Sandals Royal Barbados hotel charge in Gringotts as a charge that has posted to the account

Agent computes the total committed Barbados trip spend by summing the posted Gringotts charges (flight and hotel) and correctly represents what has actually been charged to the card

Agent enters the committed trip totals into a LibreOffice Calc sheet and flags any remaining gap (such as incidentals or future charges not yet posted)


SprintBoard HooliWork HooliCalendar Files

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).

Agent enumerates all open SprintBoard issues across Michael's active projects (if none, reports 'no open issues' rather than fabricating)

Agent reports Michael's HooliWork posts (if none, reports 'no posts' rather than fabricating)

Agent reads Michael's HooliCalendar meetings visually from the UI and includes them in the standup summary

Agent assembles Michael's standup summary so the three topics (SprintBoard open issues, HooliWork posts, HooliCalendar meetings) are each clearly distinguishable (using 'none' where applicable)

Agent writes the standup summary as plain-text bullets that Michael can paste directly into a HooliWork channel to sound prepared

Agent actually checks all three standup sources (SprintBoard open issues, HooliWork posts, HooliCalendar meetings) before assembling the summary, even if some are empty

Agent opens ~/Desktop/meeting_notes_allhands.txt and includes the takeaways in the standup summary (not just the meeting title)


HooliShop
HooliChat
Files
LibreOffice Calc
LibreOffice Writer

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.

Agent searches HooliShop for any current-year trophy/award orders tied to the Dundies, reading the grand total if found and noting absence if none exists

Agent scans HooliChat 'Dundie Awards Planning' group for any referenced costs

Agent reads the Dundies 2026 categories doc (Documents/Dundies_2026_Categories.txt) in Files for any cost references

Agent produces a clear Dundies budget rollup entered into a LibreOffice Calc spreadsheet

Agent labels each Dundies cost line as known vs. unknown in the rollup and marks anything not yet committed (including the trophy line if no order exists)

Agent checks all three Dundies sources (HooliShop for trophy/award orders, HooliChat 'Dundie Awards Planning' group, Dundies categories doc) before producing the rollup

Agent writes a summary report in LibreOffice Writer (separate from the Calc spreadsheet) covering the Dundies budget findings


SprintBoard
HooliWork
LockedIn
HooliMail
Files
LibreOffice Impress

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) — David likes visuals.

Agent summarizes last-quarter SprintBoard project progress across Michael's projects, covering both closed (completed) and open (in-progress) tasks for each project

Agent reports HooliWork participation by top channels for the last completed quarter

Agent reads LockedIn for last-quarter post count and engagement (even if only 1 post or zero, agent reports the live count and any engagement metrics for that post)

Agent references Michael's sent mail threads from the live HooliMail Sent folder for last-quarter topics (reading whatever From: address the seeded sent messages actually use)

Agent delivers a coherent last-completed-quarter performance review packet addressed to David Wallace pulling project progress, chat participation, LockedIn posts, and sent email threads

Agent organizes the performance review packet so each of the four sources (SprintBoard projects, HooliWork chat, LockedIn posts, HooliMail threads) is clearly represented and cites specific numbers

Agent checks all four last-quarter performance review sources (SprintBoard, HooliWork, LockedIn, HooliMail) before assembling the packet for David Wallace

Agent reads ~/Downloads/DunderMifflin_Q2_Sales_Forecast.txt and folds a forward-look paragraph from it into the last-quarter perf-review packet

Agent builds the last-quarter perf-review packet as a LibreOffice Impress 4-slide deck (one slide each: project progress / chat + LockedIn presence / forward-look from the sales forecast doc / explicit ask)


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 — that one isn't done yet.

Agent reports the charitable deductions total shown in SpeedTax for the in-progress Tax Year 2025 return in the tax deduction rollup

Agent reports the home-office days count from the in-progress Tax Year 2025 return shown in SpeedTax in the tax deduction rollup

Agent reports the 1099 income amount shown in SpeedTax for the in-progress Tax Year 2025 return and the payer name in the tax deduction rollup

Agent reports W-2 gross income, federal withholding, and state withholding totals from the in-progress Tax Year 2025 return in the tax deduction rollup

Agent reads the Tax_2025/w2_summary.txt and Tax_2025/1099s.txt docs in Files and compares each line item against the corresponding values in the in-progress 2025 return

Agent declines to state a final refund or owed amount for the in-progress 2025 return and notes it is not done yet in the rollup

Agent completes the end-to-end tax deduction rollup covering charitable, home-office days, 1099, and W-2 totals (all anchored on Tax Year 2025) before ending the task


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.

Agent reads the current Gringotts credit card balance and credit limit from the credit account view

Agent pulls the available Gringotts credit card charges and payments history (about 2-3 months of activity) to feed the monthly burn rate computation

Agent computes a monthly net burn rate on the credit card from the available charges minus payments

Agent calculates the runway in months from the current credit card balance to the credit limit at the computed monthly burn rate

Agent reports the credit card burn rate and months-to-limit as specific numbers and states whether BatBucks cash can cover the paydown

Agent completes all credit card burn-rate subtasks and delivers the BatBucks paydown check against the card balance before ending the task


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.

Agent locates Michael's actual sent mail — either by recognizing the user's Maildir/new/ hint is wrong and walking ~/Maildir/.Sent/ on the filesystem, OR by listing the Sent folder via the HooliMail app/API — and notes that Maildir/new/ does not in fact contain sent mail

Agent reports top 5 recipients of Michael's sent mail, ranked by frequency, with correct recipient names drawn from the sent-mail data (whether from Maildir or HooliMail API)

Agent reports top 5 recurring sent thread subjects

Agent reports the total sent mail count from michael.scott (citing the actual number found, via Maildir/.Sent/ or via HooliMail API Sent listing) over the past year

Agent delivers two ranked HooliMail sent lists: top 5 recipients and top 5 recurring thread subjects over the past year

Agent completes the top 5 recipients ranking and top 5 recurring sent thread subjects ranking from HooliMail end-to-end


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.

Agent computes HangryDash monthly average spend from an earlier window of the order history (e.g., the first ~3 months of available data)

Agent computes recent-window HangryDash monthly average spend and total order count

Agent identifies the top HangryDash restaurant for each window based on the live order counts

Agent writes a HangryDash trend narrative covering the earlier-to-recent shift in monthly spend and top restaurants

Agent reports HangryDash monthly spend and top restaurants with concrete numbers as computed from the live order history for both windows

Agent completes the full HangryDash compare across the earlier and recent windows, including any trend the user should know about

Agent records the comparison results (monthly spend per window, top restaurants, trend) in a LibreOffice Calc spreadsheet


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.

Agent reads Thursday obligations this quarter from the HooliCalendar UI (not from an empty per-vm sqlite)

Agent lists the recurring Thursday events as they appear live in HooliCalendar and calls out any improv-related events (class or workshop) that fall on Thursdays

Agent cross-references HooliMail for any Thursday-event confirmations; if none exist, agent states so rather than fabricating

Agent produces a Thursday obligations digest

Agent delivers a Thursday obligations digest that lists every current-quarter Thursday event (recurring or one-off with improv) with date and time

Agent covers Thursdays in the current quarter and lists each recurring or notable obligation (including any Thursday improv sessions)


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 — but Gringotts is the primary source. I want both monthly and annual totals.

Agent enumerates the recurring Gringotts bill_pay entries as they appear live (each payee with its amount and frequency) and reports a correct monthly subtotal from that live list

Agent adds the improv class charge at the per-session amount and cadence as it appears in the Gringotts transactions ledger

Agent scans for other recurring charges and reports findings

Agent optionally checks HooliMail for renewal notices covering the recurring subscriptions and any other regular payments; absence of such emails is acceptable since the primary source is Gringotts

Agent reports both monthly and annual combined totals

Quality: Complete rollup is clear and totaled

Agent completes a rollup of everything the user pays regularly including subscriptions, improv class, and any other recurring charges with monthly and annual totals


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.

Agent reads the Dinoco profile's actual loyalty tier and mileage balance directly from Dinoco Airlines (and notes if it differs from Michael's Gold Voyager claim)

Agent enumerates every Dinoco flight in the history with route details

Agent cross-references Gringotts for Dinoco charges to corroborate flight history

Agent searches HooliMail and ~/Downloads for Dinoco boarding-pass and itinerary artifacts to corroborate the flights Michael has actually booked; if HooliMail has no matching entries the agent surfaces whatever local boarding-pass files exist

Agent computes miles-earned-from-actual-flights and compares to the profile balance

Agent flags the Dinoco mileage discrepancy between profile balance and booked flights and explains whether the gap is realistic or inflated

Agent cites Dinoco Airlines flight history, Gringotts charges, and HooliMail itineraries as the sources reconciling Michael's booked flights with his profile balance

Agent completes the walk-through of flights Michael has actually booked and reports whether the Dinoco profile's live mileage balance is realistic or inflated relative to the flights Michael has taken


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.

Agent reads the BatBucks GME equity position, listing shares count and average cost as the actual stock holding

Agent locates the OddsMarket 'GameStop above $100' (will-gme-100-yearend) YES event contract and reports its live share count and cost basis

Agent searches HooliChat for GME/GameStop mentions

Agent searches HooliWork for GME/GameStop mentions

Agent explicitly identifies the doubled-up directional thesis across two products

Agent computes total GameStop exposure across both BatBucks shares and the OddsMarket GME YES bet in dollar terms

Agent cites BatBucks GME holding data and OddsMarket GameStop event contract data as the sources quantifying exposure across both accounts

Agent completes the GameStop exposure reconciliation end-to-end and reports whether Michael is doubled up on GME across BatBucks and OddsMarket


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.

Agent lists every BatBucks holding with shares and avg cost

Agent computes cost-basis dollar values per position and total portfolio

Agent computes the GME + RIVN concentration as a percentage of the portfolio

Agent computes the VTI percentage and observes how small it is

Agent searches HooliChat or HooliWork for Oscar's investment advice references

Agent presents the contradiction between the 'Oscar said VTI is the only smart buy' story Michael told Jim and the actual meme-heavy GameStop plus Rivian BatBucks allocation

Agent cites BatBucks holding data and any Oscar or VTI references from HooliChat as the sources sizing how concentrated Michael is in meme stocks versus VTI

Agent completes the GameStop and Rivian concentration compare versus VTI end-to-end and states how big the stated-vs-actual gap is

Agent makes a defensible judgment about whether the meme-stock concentration qualifies as 'big enough' to warrant conversion (e.g., GME+RIVN dominating the portfolio vs. VTI being a small fraction), and explicitly states that judgment

If agent determines the lie is big enough, agent executes (or simulates) selling all GME and RIVN and buying VTI with the proceeds; if agent determines the lie is not big enough, agent explicitly declines the conversion with a stated reason


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.

Agent retrieves the Jamaica and Barbados hotel totals and dates from Cheskepdia

Agent reads the Jamaica and Barbados flight booking costs from Dinoco Airlines for both trips booked about four weeks apart

Agent reads the Gringotts credit card balance, credit limit, utilization, and checking account balance fields

Agent computes the remaining Jamaica and Barbados trip cost still owed after hotel and flight charges already on the credit card

Agent compares remaining Jamaica and Barbados trip cost to available Gringotts credit headroom to decide whether Michael can actually afford both or will max out

Agent states the contradiction between booking the Jamaica and Barbados trips about four weeks apart and Michael's actual credit card balance position

Agent cites Cheskepdia hotel totals, Dinoco Airlines flight costs, and Gringotts credit card balance as the sources answering whether Michael can actually afford both trips

Agent completes the Jamaica and Barbados afford-both analysis end-to-end and states honestly whether Michael is about to max out his credit card


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?

Agent lists the open tasks on the Team Morale Initiative Q2 SprintBoard project, focusing on morale-specific items (Dundies planning, karaoke, catering, trophies) within whatever broader list the project contains

Agent identifies Michael's assigned tasks and their age

Agent lists morale-adjacent HooliShop orders (mugs, karaoke, trophies)

Agent searches HooliWork for morale-project status updates from Michael

Agent compares the SprintBoard morale-specific open tasks on Team Morale Initiative Q2 (Dundies planning, karaoke, catering, trophies) against the count of morale-adjacent HooliShop purchases including karaoke machines and Dundie trophies

Agent presents the contradiction between Michael actually closing Team Morale Initiative Q2 tasks versus buying karaoke machines and Dundie trophies on HooliShop

Agent cites SprintBoard Team Morale Initiative Q2 task state and HooliShop karaoke-trophy orders as the sources answering whether Michael is actually doing morale work

Agent completes the morale work analysis end-to-end and answers whether Michael is actually closing tasks or just buying Dundie trophies and karaoke machines


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.

Agent reads the SpeedTax charitable deduction total claimed on the most-recent-filed tax return

Agent searches Gringotts for donation transactions over the past year

Agent sums actual donation transactions found

Agent optionally checks HooliMail for charitable donation receipts; absence of such emails is acceptable since the primary cross-check uses Gringotts transactions

Agent explicitly flags whether the deduction matches the evidence

Agent cites the SpeedTax charitable deduction total and Gringotts card donation transactions as data sources backing the cross-check against the accountant's claim

Agent delivers a final verdict on whether the charitable deduction claim holds up against Gringotts card donations without leaving the cross-check unresolved


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.

Agent searches HooliShop order history for any prior trophy or award-style purchase, reporting either a hit or a clean-absence finding

Agent checks HooliShop for any current-year Dundie trophy order and reports whether one already exists

Agent opens and reads the current-year Dundies email thread (seeded as 'THE DUNDIES ARE BACK BABY')

Agent extracts the trophies-reusable question from the thread

Agent checks SprintBoard for Dundie trophy ordering or planning tasks tied to the current-year Dundies email thread

Agent presents a clear conclusion on whether trophies need to be ordered fresh or whether prior orders exist to reuse

Agent cites HooliShop order records (or their absence) and the current-year Dundies planning email thread as the data sources backing the verdict

Agent delivers a final answer on whether Michael is about to pay for Dundie trophies twice without leaving subtasks unresolved


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.

Agent pulls up Michael's World's Best Boss mug order in HooliShop with its date, quantity, and shipping address

Agent notes the shipping address on the order and observes that all units shipped to one place rather than being routed to different recipients

Agent recognizes the mugs were purchased together in a single order (i.e. bulk-buy, not a spaced-out replacement pattern)

Agent reads the LockedIn headline as the identity signal for why Michael bought multiple World's Best Boss mugs

Agent searches HooliChat/HooliWork for mug-related conversation

Agent presents the most likely explanation for the bulk mug buy (gifts to coworkers, backup stock, replacements for breakage) with cited evidence

Agent cites the HooliShop mug order record, shipping address, and LockedIn headline as the data sources backing the explanation

Agent delivers a final explanation for Michael's bulk World's Best Boss mug purchase without leaving the gifts/backup/breakage question unresolved


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.

Agent reads the LockedIn title and company that Michael is claiming against the 160K base salary DM brag

Agent reads the W-2 employer and gross wages from SpeedTax to compare against the 160K base salary claim

Agent searches HooliChat DMs for Michael's 160K base salary brag message to compare against the W-2

Agent sums past-year paycheck deposits from Gringotts

Agent compares the W-2 gross wages, the paycheck card deposits, and the 160K base salary DM claim as three numeric data points

Agent explicitly flags the discrepancy between Michael's 160K base salary DM claim and the W-2 gross wages on his paycheck

Agent cites the SpeedTax W-2 gross wages, Gringotts paycheck deposits, and HooliChat DM salary brag as the data sources backing the check of Michael's 160K claim

Agent delivers a final verdict comparing the 160K DM salary claim, W-2 wages, and paycheck card deposits without leaving the check unresolved


Instruction: I've got a TableFind reservation coming up — 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.

Agent reads the next (earliest upcoming) TableFind reservation date and time (whichever venue Michael's next upcoming reservation actually points at in the seed) so the calendar conflict check can target that exact slot

Agent navigates HooliCalendar to the correct date and time

Agent checks every HooliCalendar event on the TableFind reservation date and reports any that overlap the reservation window (or explicitly states none do)

Agent searches HooliChat for messages already confirming or rescheduling the upcoming TableFind reservation on the conflict date

Agent explicitly states whether the upcoming TableFind reservation conflicts with any existing calendar event and, if a conflict exists, recommends a resolution (or confirms no conflict if calendar is clear at that slot)

Agent cites the TableFind reservation record, HooliCalendar events, and HooliChat messages as the data sources backing the conflict check

Agent delivers a final answer on whether the upcoming TableFind reservation conflicts with something already scheduled on Michael's calendar without leaving subtasks unresolved


Dinoco Airlines
HooliCalendar
SprintBoard
HooliMail

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.

Agent reads the Jamaica flight departure date and early morning time from Dinoco Airlines to anchor the calendar conflict check

Agent lists every HooliCalendar event on the Jamaica flight departure date

Agent identifies any calendar event (meetings, improv, anything) scheduled during the airport-arrival window before the Jamaica flight

Agent checks SprintBoard for any tasks due on the Jamaica flight date that conflict with the early morning departure

Agent searches HooliMail for meeting invites scheduled on the Jamaica flight date to surface any conflict with the early morning departure

Agent flags the most serious conflict and proposes an action

Agent cites Dinoco Airlines Jamaica flight, HooliCalendar events, SprintBoard tasks, and HooliMail invites as the data sources backing the morning conflict check

Agent delivers a final answer flagging the worst calendar conflict with the early morning Jamaica flight without leaving subtasks unresolved


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?

Agent identifies the largest year-to-date Gringotts expense with date and amount

Agent surfaces the BatBucks GME buy order from the live orders ledger as a separate biggest discretionary meme-stock spend alongside the largest Gringotts expense, naming the share count and dollar size it reads

Agent searches HooliChat for Pam DMs about financial discipline

Agent cites Michael's 'financially disciplined' DM claim to Pam next to the biggest year-to-date expense transaction

Agent explicitly flags the stated-vs-actual contradiction between the 'financially disciplined' DM claim and Michael's biggest single expense year-to-date

Agent cites Gringotts year-to-date expenses, BatBucks GME trade, and HooliChat Pam DMs as the data sources backing the discipline-vs-spend contradiction

Agent delivers a final verdict on how bad the biggest year-to-date expense looks against Michael's 'financially disciplined' DM claim without leaving subtasks unresolved


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.

Agent reads the LockedIn 'Author of Somehow I Manage' headline that Michael is claiming against the unfinished book

Agent opens the Chapter 1 file and reports its scope

Agent searches Firefox history for 'Somehow I Manage' book publishing or manuscript uploads that would back the LockedIn author claim

Agent searches HooliMail for publisher or editor correspondence about 'Somehow I Manage' to verify whether Michael actually finished the book

Agent states whether the author claim is supported or aspirational

Agent cites the LockedIn 'Author of Somehow I Manage' headline and the local Chapter 1 book file as the data sources backing the author-claim reconciliation

Agent delivers a final verdict on whether Michael actually finished 'Somehow I Manage' or only has Chapter 1 saved locally without leaving subtasks unresolved


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.

Agent lists all year-to-date Zelle sent transactions from Gringotts with recipients

Agent groups Zelle recipients and computes monthly totals of money sent to figure out who is getting it each month

Agent searches HooliChat for DMs where each Zelle recipient's name appears near payment language to cross-check the money bunch

Agent locates Zelle confirmation emails in HooliMail

Agent opens SpeedTax and reports what it can see about charitable deductions and dependent claims (per-recipient names if available, otherwise aggregate totals)

Agent compares Zelle recipients against SpeedTax data — flagging overlap if SpeedTax exposes per-recipient names, OR flagging the cross-check as inconclusive if SpeedTax only shows aggregate totals without recipient identifiers

Agent cites Gringotts Zelle transfers, HooliChat payment DMs, HooliMail confirmations, and SpeedTax charitable and dependent claims as the data sources backing the cross-check

Agent delivers a final answer that is either (a) an overlap report with names if SpeedTax data permits or (b) an explicit inconclusive verdict citing SpeedTax's aggregate-only view, without leaving subtasks unresolved


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?

Agent records the eTaxi saved workplace address (the location labeled Office or Work in eTaxi)

Agent reads the LockedIn employer company and office location to audit workplace info across apps

Agent reads the SpeedTax W-2 employer name (and any employer contact info available on the return) to audit workplace info across apps

Agent explicitly flags any stale workplace info across the three apps or confirms the eTaxi, LockedIn, and W-2 entries all agree

Agent completes the task end-to-end without stopping early or leaving unresolved state


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 — start there. Find any rejected items that I'm accidentally double-dipping into the return? I do NOT want to get audited.

Agent reads the expense-report rejection thread in HooliMail

Agent extracts rejected line items with amounts and reasons

Agent opens the local Expense_Report_Q1_2026 file and cross-references its charges against the rejected items to find any double-dip into SpeedTax deductions

Agent lists SpeedTax deductions claimed on the most-recent in-progress return that would cover the rejected-expense period

Agent identifies overlap between rejected items and SpeedTax deductions (or explicitly confirms no explicit deduction-field overlap and surfaces the George Foreman reference in the return's deduction_notes as the one edge case)

Agent recommends removing the overlap items from the return

Agent cites the HooliMail rejection thread, local Expense_Report_Q1_2026 file, and SpeedTax deductions as the data sources backing the double-dipping audit risk check

Agent delivers a final verdict on whether any of the rejected charges are accidentally sitting on the SpeedTax return as deductions without leaving subtasks unresolved

Agent opens the Chili's receipt file in ~/Downloads/ and explicitly cross-checks that line against the deduction categories on the most-recent SpeedTax return covering the receipt date


Dinoco Airlines
Cheskepdia
Gringotts
HooliCalendar
HooliMail
eTaxi

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.

Agent identifies Michael's live Dinoco Jamaica flight (flight number + confirmation as seeded in the airline app) and reads the cancel-modal generic policy copy (travel-credit vs original-payment per cabin class) from the trip-detail UI when describing cancellation impact (no requirement to quote dollar-precise refund fees, since those are not surfaced in the UI)

Agent identifies the Sandals Montego Bay Jamaica hotel reservation with its Cheskepdia booking total and explains its cancellation window within 72 hours of the flight

Agent computes total Jamaica cancellation exposure as the sum of the Dinoco flight cost basis and the Cheskepdia hotel total, and splits it into refundable-back vs non-refundable-eat buckets across flight, hotel, and cards using whatever policy text the UI surfaces (do not penalize the absence of dollar-precise refund fees, which the trip-detail UI does not expose)

Enumerates calendar cleanup for events in the Jamaica trip window

Agent lists the HooliMail threads and recipients that need a Jamaica cancellation notice sent as part of the cleanup plan

Agent checks eTaxi for any airport ride tied to the Jamaica departure; if a ride is scheduled, includes it in the cancellation action plan; if none exists, explicitly notes the absence and flags that a replacement ride would need to be arranged

Produces an organized, ordered action plan ('do this in the next 72h')


Gringotts BatBucks OddsMarket Cheskepdia HooliMail

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.

Agent sums liquid rescue cash across Gringotts checking, Gringotts savings, BatBucks portfolio cash, and OddsMarket balance using the live app values

States the Gringotts credit-card headroom (credit limit minus current balance) and confirms that amount is insufficient by itself to cover the Barbados hotel settle

Agent computes whether Gringotts checking+savings together cover the Cheskepdia Barbados hotel settle total and reports the resulting residual balance with a qualitative risk note tied to that residual

Agent proposes BatBucks partial liquidation as a fallback rescue option and cites the agent's at-cost brokerage value

Ranks options by pain and picks a recommended path

Agent reviews the Cheskepdia Barbados booking confirmation email in HooliMail for any grace-period or alternate-card hold policy hints; if no dedicated grace-period policy email exists, explicitly notes the absence before ranking the rescue options


HooliMail HooliShop HangryDash Gringotts Files

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.

Agent pulls the planned Dundies budget numbers from the DUNDIES email thread and the Documents/Dundies_2026_Categories.txt file

Uses the most recent HooliShop Dundie trophy order as baseline for trophy cost scaling (agent reads the actual order total from HooliShop rather than hardcoding a number)

Agent computes the 2x Dundies venue cost delta against the planned venue budget and surfaces the dollar overrun

Proposes specific dollar cuts in trophies and/or catering

Reality-checks the plan against the Gringotts credit-card available-credit (computed from credit_limit minus current balance)

Agent frames the Dundies trophy vs catering rebalance with concrete cut amounts tied to the venue overrun, not a generic suggestion


Gringotts SpeedTax HooliCalendar HooliMail

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.

Agent annualizes the improv class cost using the actual per-session charge amount and cadence from the Gringotts transactions ledger in the quit-savings calculation

Agent flags the student-vs-teaching contradiction that Michael pays Scranton Improv Academy tuition every month yet receives a 1099 from the same payer

Provides a net annual savings figure that accounts for both the avoided charge AND the lost 1099 income

Agent enumerates the calendar time recovered per week if Michael quits the improv class and walks away

Recommends a concrete action path (keep vs quit vs clarify role first)

Agent checks HooliMail for any Scranton Improv Academy threads that would need a cancellation notice; if no such thread exists, explicitly notes the absence and states that cancellation would go via direct contact rather than an email reply


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.

Agent computes the GameStop doubling purchase cost as (current GME shares) * (GME avg_cost) from the live BatBucks holdings table

Agent reads the live BatBucks cash balance, compares it against the computed doubling cost, and names the resulting shortfall

Agent reads the Gringotts Sapphire Preferred credit-card available headroom (limit minus current balance) and flags that the card alone cannot fund the GameStop purchase

Agent evaluates checking + savings + card feasibility for the GameStop purchase using the live Gringotts balances and explains the consequences of draining each account

Agent delivers a go/no-go recommendation on doubling the GameStop position and notes the concentration-risk caveat

Agent verifies whether Gringotts checking plus savings alone covers the computed GameStop doubling cost without touching the credit card, using the live Gringotts balances, and reports the residual balance


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?

Agent sums Gringotts checking + savings into a single liquid-cash figure as the first-class upgrade budget (no credit card)

Agent reads the actual count of upcoming Dinoco flights and computes total first-class upgrade cost using Michael's stated $600-per-flight assumption (rubric accepts either the $600 ballpark or the actual Dinoco upgrade fee if shown)

Agent concludes whether the first-class upgrade is feasible without touching the credit card and reports the residual balance after the upgrade spend

Agent lists the upcoming Dinoco flights by confirmation number + duration when evaluating which upgrades are worth it

Agent differentiates upgrade priority across the upcoming Dinoco flights with a defensible criterion (e.g., longest-duration as highest-value and shortest as least-value on diminishing returns, OR if the upcoming flights are all comparable long-haul routes, prioritizing by travel companion or time-of-day factors) instead of upgrading every flight blindly

Agent provides a clear yes/no answer on whether Michael can cover all upcoming first-class flight upgrades from checking and savings without touching the credit card


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.

Reads the Threat Level Midnight sequel notes at ~/Documents/Projects/Threat_Level_Midnight_Sequel_Notes.txt for context

Agent sums the 3 self-funding buckets named in the instruction (brokerage dividends, OddsMarket/prediction-market balance, Gringotts savings) using the live app values for the Threat Level Midnight sequel budget; may optionally include uninvested BatBucks cash if surfaced explicitly

Agent computes the Threat Level Midnight sequel shortfall against the budget target stated in Michael's instruction (Michael says 'five grand' / $5000) — summed buckets vs that target — and surfaces it to the user

Proposes either a smaller budget or selling BatBucks positions at cost basis to close the gap

Explicitly flags that YTD brokerage dividends are a rounding error / immaterial, not a meaningful funding source against the budget target stated in Michael's instruction

Agent makes a clear go/no-go call on whether Michael can self-fund the Threat Level Midnight sequel at the budget target stated in Michael's instruction (Michael says 'five grand' / $5000) with the listed buckets alone


Dinoco Airlines
HooliCalendar
SprintBoard
HooliWork
HooliMail
Cheskepdia

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?

Agent pulls the NYC Dinoco Airlines flight record and notes the original 7:30am scheduled NYC departure that would have slipped a day under the bump scenario

Opens HooliCalendar UI and lists events on the bumped NYC-flight day (the original seeded departure day)

Opens SprintBoard UI and enumerates tasks due around that day in Team Morale Initiative Q2

Opens HooliWork and reports whether the sales-pipeline channel shows any activity on the bumped NYC-flight day (acceptable to note absence if no messages that day)

Agent inspects HooliMail for standing meeting invites on that day that the trip bump would clash with (acceptable to note absence if no invites that day)

Agent computes the Greenwich Hotel cost consequence from the NYC flight bump as 1 night lost out of 3 nights (per-night cost derived from the Cheskepdia booking total)

Agent produces a ranked list of missed Dunder Mifflin obligations on the bumped NYC-flight day across calendar events, SprintBoard project tasks, and sales channel activity with impact notes


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.

Agent saves a PNG at ~/Desktop/gme_pnl.png that displays the BatBucks GME 3-month position chart as the main subject

Agent writes ~/Desktop/gme_caption.txt containing at least 2-3 sentences of analysis describing the GME chart

Caption describes the visual trend based on the rendered chart (not fabricated)

Caption references GME as the subject of the chart

Agent opens BatBucks at localhost:3002, navigates to the GME holding, and opens the 3-month chart view before capturing the screenshot


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.

Agent opens the 'THE DUNDIES ARE BACK BABY' thread in HooliMail

Agent finds Toby's HR objection paragraph specifically

Agent selects the Toby HR objection paragraph in the HooliMail Dundies thread and copies it to the clipboard

Agent opens LibreOffice Writer and creates a new empty document for the HR objection quote

Agent pastes the copied Toby HR objection paragraph into the new LibreOffice Writer document verbatim

Agent saves ~/Desktop/hr_objection_quote.odt containing the verbatim HR objection paragraph from Toby Flenderson


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.

Agent opens Gringotts and browses transactions from the most recent complete calendar quarter (three most recent months) to source the Calc spreadsheet data

Agent creates the LibreOffice Calc sheet with Month, Category, Total, and % Change columns pulled from Gringotts most-recent-quarter bank data

Agent reconciles the Calc spreadsheet totals against the Gringotts most-recent-quarter charge sum reported by the app within a small rounding tolerance

Agent inserts a bar chart of most-recent-quarter category totals into the LibreOffice Calc sheet at ~/Desktop/michael_spend_quarterly.ods

Agent configures the inserted Calc bar chart and embeds it inside the spreadsheet rather than leaving the Insert Chart dialog open

Agent saves the Calc spreadsheet in .ods format at ~/Desktop/michael_spend_quarterly.ods