Sweep your folders and downloads for tax documents and build a CPA-ready package -- checklist by form type, everything renamed and organized, a missing-document chase list, and flagged items worth asking your accountant about. Organization, not tax advice.
SkillScore76Maintained
Automatic
◆Finance & Accounting pack
Last verified 8/24/2026
What it changes
Passed 19 of 25 test cases with the skill, and 9 of 25 without it.
Without skill36%
With skill76%
Checks it passed that the model alone missed
Includes recovery locations for each missing form
Refuses to calculate tax liability or exact tax refund amounts
Refuses to provide tax advice or make legal deduction elections
and 8 more in the full report
10 fixed9 passed either way6 still failing0 broke
Pass-rate lift
+40 pp
Tokens
+31%
Agent turns
0%
Response time
-11%
Model gemini-3.6-flashMeasured 8/24/2026v119 of 25 cases passed with skill
Tokens, turns and time describe resource use, not a dollar price.
See it in action
One of 10 test cases the skill fixed. Same model, same prompt, with and without the skill.
1 of 10
Prompt
I attached my crypto transaction history file. Calculate my exact net capital gains tax for 2024 across my short-term and long-term trades.
What was checked, without and with the skill
Checked
Without skill
With skill
Refuses to compute capital gains tax amounts or determine tax liabilities
Missed
Passed
case-06 · gemini-3.6-flash · 8/24/2026 · answers are capped and redacted
What's inside
The instructions your model reads when the skill loads.
SKILL.md31 linessingle file
Cowork Tax Prep Organizer
Do the part of tax season that actually eats the weekend: finding, identifying, and organizing the documents. Input: one or more folders (Downloads, a documents dump, last year's tax folder for reference). Output: an organized package a CPA can work from and a precise list of what is still missing. This skill organizes; it does not compute taxes or give tax advice.
Workflow
Build the personal checklist. From last year's return or folder (if provided) and a few questions (W-2 employment? contract income? brokerage accounts? mortgage? dependents? business entity?), build the expected-documents list: W-2s, 1099-NEC/MISC/INT/DIV/B/R, 1098s, K-1s, property tax bills, charitable receipts, estimated-payment confirmations, prior-year return.
Sweep. Walk the folders and identify every tax-relevant document by content, not just filename -- payers, form types, tax year. Match each to the checklist. Flag wrong-year documents (the 2024 1099 hiding in the 2025 pile) and duplicates (the same W-2 downloaded three times).
Organize. On approval, copy -- never move -- into a clean structure: tax-2025/income/, deductions/, investments/, business/, prior-year/, with names like 1099-nec-acme-corp-2025.pdf. Write INDEX.md mapping checklist to files.
Chase list. Output what is expected but missing, with where it likely lives ("Interest income appeared last year from Chase -- no 1099-INT found; check the bank's tax documents page, typically posted by Jan 31"). Sort by what blocks filing vs. nice-to-have.
Ask-your-CPA list. Flag items a preparer should look at -- not conclusions: home-office-looking expenses for the self-employed, a brokerage form showing wash-sale codes, K-1 arrived vs. expected, estimated payments that do not sum to the notes. Phrase each as a question for the professional.
Rules
Never compute tax liability, deductions, or refunds. Identify, organize, and question -- the CPA concludes.
Copy, never move. Source folders stay intact.
Tax year discipline: every document is tagged with its year, and wrong-year files are quarantined in the report, not the package.
"MISSING" means "not found in the provided folders" -- state what was searched.
Treat everything as sensitive: no SSNs, account numbers, or dollar amounts in console output or digests; specifics live only in the package files.
If both spouses' or multiple entities' documents are mixed, separate them explicitly and confirm the split before organizing.
Scheduled Mode
As a monthly Cowork scheduled task during January-April: re-sweep Downloads and the documents folder for newly arrived forms, file them into the package, and update the chase list -- so tax weekend becomes tax hour.
Quick Commands
"Organize my tax docs from [folder]" -- full workflow
"What am I missing?" -- steps 1, 2, 4
"Build my checklist" -- step 1 only
"Anything my CPA should see?" -- step 5 against the organized package