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, pull 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?" → Pull YTD P&L from QuickBooks → 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: USD X — see full breakdown below"

User: "I need to send out 1099s" → Pull all contractor/vendor payments from QuickBooks + PayPal + Stripe → Identify contractors paid ≥ USD 600 YTD → Flag records missing W-9 / EIN → Output: 1099-NEC candidate list + missing W-9 action list ```

## Step 0 — Check the country first

Both paths below are **US federal tax**: self-employment tax, the federal bracket table, 1099-NEC and W-9. Before choosing a mode, read `Country` from the `## Business context` block (rule: `../../shared/currency-and-locale.md`). If it is absent, ask.

- **US** → continue to Determine mode. - **Anything else** → say so in one line and stop the US math: *"The quarterly-estimate and 1099 paths here are built for US federal tax. Your books are in the UK, so I'll get your closed-books packet ready for your accountant instead of a US estimate."* Then offer `/close-month` for the periods in scope. Do not run a US calculation on a non-US business, and do not relabel one as a generic estimate.

Every amount in the output is in the business's currency code; the USD 600 line is US law and is named as such.

## 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?"

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## Path 1: Quarterly estimated tax

### 1. Pull YTD financials

Use the connected ledger (MYOB, NetSuite, QuickBooks, Xero, or Zoho Books — peers, per `../../shared/connector-neutrality.md`) to pull a Profit & Loss report from January 1 of the current year through the last day of the most recently completed quarter. Capture: - **Gross revenue** (total income) - **Total expenses** (operating expenses, COGS, etc.) - **Net ordinary income** = revenue − expenses

If no ledger is connected, ask the user to upload a P&L as CSV or paste the key numbers. For field names and query approach per ledger, see [reference/connector-queries.md](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](reference/calculation-assumptions.md) for the full math and the assumptions table you must include in output.

**First, annualize.** The math runs on projected full-year net profit, not YTD: `annualized net = YTD net ÷ months elapsed × 12`. Show both, labeled. Seasonal business: ask rather than straight-lining.

Short version, all six steps running on **annualized** net profit: 1. **SE tax** = annualized net profit × 0.9235 × 0.153 (then halve it — the deductible half offsets income) 2. **Adjusted net** = annualized 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 still ahead 6. **Safe harbor check** — note whether the user should verify against prior-year tax (100% of prior year, or 110% if AGI > USD 150k)

**If a due date has already passed unpaid**, name it and show the catch-up on its own line, separate from the next payment. Penalty and interest go to the accountant — flag that they apply, never estimate them. With no quarters left, it is due with the return.

### 4. State assumptions and deliver output

The full section-by-section document structure is in [reference/output-formats.md](reference/output-formats.md).

Two things that are not negotiable: the **tax year appears in the header**, and the **Assumptions s