Tax Season Organizer

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.

Quick start

Determine which mode the user needs, ask them to upload or paste the relevant data, calculate or compile, and deliver a structured document the accountant can work from directly.

User: "what do I owe for estimated taxes this quarter?"
→ Ask the user to upload their YTD P&L export (e.g., a QuickBooks P&L exported as CSV) or paste the figures
→ Calculate estimated federal income tax + SE tax
→ Subtract payments already made this year
→ Show Q-specific amount due with due date and assumptions stated
→ Output: "Estimated Q2 payment due June 16: $X — see full breakdown below"

User: "I need to send out 1099s"
→ Ask the user to upload their contractor/vendor payment exports (QuickBooks, PayPal, Stripe) as CSV or paste the figures
→ Identify contractors paid ≥ $600 YTD
→ Flag records missing W-9 / EIN
→ Output: 1099-NEC candidate list + missing W-9 action list

Determine mode

Read the user's message and context to decide which path applies:

• Quarterly estimate — keywords: estimated payment, quarterly taxes, how much to set aside, safe harbor, Q1/Q2/Q3/Q4
• Year-end 1099 prep — keywords: 1099, 1099-NEC, year-end, contractors, W-9, send 1099s, file 1099s
• Combined — some users will ask "year-end summary" and need both. Run quarterly last; run 1099 prep first since it drives the most action items.

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?"

Path 1: Quarterly estimated tax

1. Gather YTD financials

Ask the user to upload their Profit & Loss export (e.g., a QuickBooks P&L exported as CSV) covering January 1 of the current year through the last day of the most recently completed quarter, or to paste the key figures. Capture:

• Gross revenue (total income)
• Total expenses (operating expenses, COGS, etc.)
• Net ordinary income = revenue − expenses

If the user hasn't provided the P&L yet, ask them to upload the CSV export or paste the key numbers before proceeding. For field names and what to look for, see reference/connector-queries.md.

2. Ask about prior estimated payments

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.

3. Calculate estimated liability

See reference/calculation-assumptions.md for the full math and the assumptions table you must include in output.

Short version:

1. SE tax = net profit × 0.9235 × 0.153 (then halve it — the deductible half offsets income)
2. Adjusted net = net profit − (SE tax / 2)
3. Federal income tax = apply the bracket rate appropriate to the user's business type and estimated annual income (default to 22% unless the user tells you their bracket; note this assumption explicitly)
4. Total annual liability = federal income tax + SE tax
5. Quarterly payment = (total annual liability − payments made) ÷ quarters remaining
6. Safe harbor check — note whether the user should verify against prior-year tax (100% of prior year, or 110% if AGI > $150k)

4. State assumptions and deliver output

Use this output structure:

Structure the output as a document with these sections in order:

1. Header — H2 with "Estimated tax summary" followed by the quarter and year. Subline: prepared date and "For review by your accountant."

2. 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).

3. Self-employment tax — Show the SE tax calculation: net profit times 92.35% times 15.3%, and the deductible SE half.

4. Federal income tax estimate — Adjusted net income, assumed bracket (default 22%, note to confirm with accountant), and the federal estimate.

5. Total estimated annual liability — SE tax plus federal income tax.

6. Quarterly payment — Total liability minus payments already made, divided by quarters remaining, with the specific dollar amount due and the due date.

7. Safe harbor note — Remind the owner to ensure total payments meet 100% of prior-year tax (or 110% if AGI exceeded $150k).

8. 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).

Path 2: Year-end 1099 prep

1. Gather contractor payments from all sources

You need all payments made to individuals or businesses for services in the tax year. Do not include payments for goods, refunds, or internal transfers. Ask the user to upload their payment exports (or paste the figures) from each source they use.

QuickBooks: Ask the user to export a payee-level report and upload the CSV:

"To build your 1099 list I need payee-level detail. 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."

Map columns: payee name, amount, date, payment method, EIN/SSN status. Then follow the aggregation and threshold logic below.

For field names and what to look for, see reference/connector-queries.md.

PayPal: Ask the user to export and upload 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: Ask the user to export and upload all transfers/payouts made to external parties. Same 1099-K caveat as PayPal applies.

Direct CSV: If the user uploads a CSV directly (without going through a QuickBooks export), map columns: payee name, amount, date, payment method, EIN/SSN status.

If the user hasn't provided the payment data yet, ask them to upload the relevant CSV exports or paste the numbers before proceeding.

2. Aggregate by payee

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).

3. Apply the $600 threshold

• Flag for 1099-NEC: any payee paid ≥ $600 for services (contractors, freelancers, consultants)
• Flag for 1099-MISC: any payee paid ≥ $600 for rent, attorney fees, prizes/awards
• Near-threshold alert: flag payees paid $400–$599 — close to the threshold, accountant may want to verify

Corporations (Inc., Corp., LLC taxed as C or S corp) generally do not need a 1099-NEC — note this but flag for accountant confirmation.

4. Check W-9 status

For each flagged payee, note whether a W-9 / EIN is on file per the uploaded data. Mark as:

• ✅ W-9 on file (EIN/SSN recorded in the export)
• ⚠️ Missing — W-9 not on file; must collect before filing
• ❓ Unknown — cannot determine from available data

5. Deliver the 1099 prep package

Use this structure:

Structure the 1099 prep output as a document with these sections:

1. Header — H2 with "1099 prep list" and the tax year. Subline: prepared date, "For review by your accountant," and "Not tax advice."

2. 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.

3. 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.

4. 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.

5. Near-threshold table — Payees paid $400-$599 flagged for accountant review, with a note to verify no additional payments were missed.

6. 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.

7. 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.

Guardrails

• Not tax advice. Open every deliverable with this: "Prepared for review by your accountant — not tax advice." Include it in the document header, not just in chat.
• State every assumption. If you assumed a 22% bracket, say so. If you excluded state taxes, say so. The accountant will adjust; give them the levers.
• Don't merge payees automatically. Flag likely duplicates for human review.
• Don't file anything. The output is prep material. Filing is out of scope.
• Corporation exemption is a judgment call. Note it; don't auto-exclude.

Reference files

• reference/calculation-assumptions.md — full tax math, bracket table, and SE tax walkthrough
• reference/connector-queries.md — what data to ask the user to export from QuickBooks, PayPal, and Stripe
• reference/gotchas.md — Good / Bad patterns for common failure modes
• reference/examples/quarterly-estimate.md — worked quarterly estimate example
• reference/examples/year-end-1099.md — worked year-end 1099 prep example