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npx skills add anthropics/knowledge-work-plugins --skill tax-season-organizer
Prepares tax-season materials for small business owners — framed as deliverables for their accountant, not tax advice. Two modes: (1) quarterly estimated tax calculation — pulls YTD net income from QuickBooks and calculates the federal income tax + self-employment tax liability and quarterly payment due; (2) year-end 1099 prep — scans QuickBooks, PayPal, and Stripe for contractors paid over $600, builds a 1099-NEC candidate list with missing W-9 flags, and produces a plain-English summary a CPA can work from directly.
npx skills add anthropics/knowledge-work-plugins --skill tax-season-organizer
Framing: This skill produces prep material for a CPA, not tax advice. Say so early and state every assumption explicitly so the accountant can adjust.
Determine which mode the user needs, pull the relevant data, calculate or compile, and deliver a structured document the accountant can work from directly.
Read the user's message and context to decide which path applies:
If the intent is ambiguous, ask: "Are you looking at your estimated tax payment for this quarter, or are you preparing 1099s for your contractors — or both?"
Use QuickBooks to pull a Profit & Loss report from January 1 of the current year through the last day of the most recently completed quarter. Capture:
If QuickBooks is not connected, ask the user to upload a P&L as CSV or paste the key numbers. For field names and query approach, see reference/connector-queries.md.
Before calculating, ask: "How much have you already paid in estimated taxes so far this year?" If the user doesn't know, note that you'll calculate total liability — they can subtract payments themselves or check with their accountant.
See reference/calculation-assumptions.md for the full math and the assumptions table you must include in output.
Short version:
Use this output structure:
Structure the output as a document with these sections in order:
Header — H2 with "Estimated tax summary" followed by the quarter and year. Subline: prepared date and "For review by your accountant."
YTD snapshot — Bold lines showing YTD net profit with date range, estimated annual net profit (annualized from YTD), and assumed business type (sole proprietor, S-corp, etc. — flag as assumed, not confirmed).
Self-employment tax — Show the SE tax calculation: net profit times 92.35% times 15.3%, and the deductible SE half.
Federal income tax estimate — Adjusted net income, assumed bracket (default 22%, note to confirm with accountant), and the federal estimate.
Total estimated annual liability — SE tax plus federal income tax.
Quarterly payment — Total liability minus payments already made, divided by quarters remaining, with the specific dollar amount due and the due date.
Safe harbor note — Remind the owner to ensure total payments meet 100% of prior-year tax (or 110% if AGI exceeded $150k).
Assumptions — Bullet list of every assumption: bracket rate, business structure, state taxes excluded, deductible SE half included, and deductions not applied (home office, QBI, depreciation).
Query each connected source for all payments made to individuals or businesses for services in the tax year. Do not include payments for goods, refunds, or internal transfers.
QuickBooks — try live connector first, fall back to CSV if needed:
Try live connector. Attempt to pull vendor-level payment records via the QuickBooks MCP. If the connector returns individual payee records with name, amount, and account category, use them directly and skip the CSV step.
Detect aggregate-only response. If the MCP returns only category-level totals (e.g. "Contract labor: $7,500" with no payee breakdown), the connector does not yet support vendor-level queries. In this case, prompt the user:
"QuickBooks returned summary data only — I need payee-level detail to build your 1099 list. Please export a Transaction List by Vendor report (QuickBooks → Reports → Expenses → Transaction List by Vendor, filtered to this tax year) and upload the CSV here. I'll process it automatically."
Process CSV via Desktop connector. Map columns: payee name, amount, date, payment method, EIN/SSN status. Follow the same aggregation and threshold logic below regardless of whether data came from the live connector or CSV.
Note for future connector versions: If the QuickBooks MCP is upgraded to expose vendor payment records directly, step 1 will succeed and the CSV fallback will be skipped automatically. No changes to this skill are needed — the try-first logic handles it.
For field names and query approach, see reference/connector-queries.md.
PayPal: Pull all "Goods & Services" payments sent. Note: PayPal issues its own 1099-K to contractors above the threshold — flag these separately in output so the accountant can determine whether a 1099-NEC is also needed.
Stripe: Pull all transfers/payouts made to external parties. Same 1099-K caveat as PayPal applies.
Desktop/CSV: If the user uploads a CSV directly (without going through QuickBooks export), map columns: payee name, amount, date, payment method, EIN/SSN status.
Combine across sources and sum payments by individual or business entity. Deduplicate by name (watch for "John Smith" vs "John A. Smith" — flag likely duplicates for human review rather than auto-merging).
Corporations (Inc., Corp., LLC taxed as C or S corp) generally do not need a 1099-NEC — note this but flag for accountant confirmation.
For each flagged payee, note whether a W-9 / EIN is on file in QuickBooks. Mark as:
Use this structure:
Structure the 1099 prep output as a document with these sections:
Header — H2 with "1099 prep list" and the tax year. Subline: prepared date, "For review by your accountant," and "Not tax advice."
Summary — Bullet counts: total contractors paid, number requiring 1099-NEC (at or above $600 for services), number missing W-9 (with filing deadline note for Jan 31), and number near-threshold flagged for review.
1099-NEC candidates table — Columns: payee name, total paid, data sources, W-9 status (on file / missing / unknown), and notes. Flag any payee paid via PayPal or Stripe with a note that the platform may issue its own 1099-K.
Missing W-9 action list — Numbered list of contractors who need to provide a W-9 before filing, with amounts paid and a reminder to request the form.
Near-threshold table — Payees paid $400-$599 flagged for accountant review, with a note to verify no additional payments were missed.
Payment processor note — Explain that PayPal and Stripe issue their own 1099-K forms and the accountant should confirm whether a 1099-NEC is also needed for contractors paid exclusively through those platforms.
Next steps checklist — Action items for the accountant: collect missing W-9s, confirm unknowns, review near-threshold payees, verify corporation exemptions, confirm 1099-K overlap handling, file by January 31.