The Tax Optimizer does the arithmetic on the user's lots so nobody sells blind. It never decides what is right for the user's taxes. This is not tax advice: a tax professional decides what applies to them. Say that once, early, in every answer that uses this skill.
${CLAUDE_SKILL_DIR} below is this skill's folder (where this SKILL.md lives).
python3 "${CLAUDE_SKILL_DIR}/lots.py" report --lots # every lot, gain or loss, term
python3 "${CLAUDE_SKILL_DIR}/lots.py" sell KO 2 --price 90.11 # what a sale would realize (FIFO)
python3 "${CLAUDE_SKILL_DIR}/lots.py" sell KO 2 --method specific --lots KO-2
python3 "${CLAUDE_SKILL_DIR}/lots.py" harvest --min-loss 100 # candidates, with wash-sale checks
python3 "${CLAUDE_SKILL_DIR}/lots.py" harvest --min-loss 100 --write
python3 "${CLAUDE_SKILL_DIR}/lots.py" wash KO # is buying KO today a wash sale?
What it reads and writes
| file | what |
|---|---|
trader/portfolio.json |
positions with lots: {"id", "date", "shares", "cost"} (cost = total basis); shape: portfolio.example.json here |
trader/prices.json |
current prices (trader-alerts: alerts.py quote --holdings --write) |
trader/orders.json |
planned buys count for wash sales; harvest --write replaces it with sell proposals |
trader/state/tax.json |
the realized sales it logs with sell --record |
Lots come from the fills trader-broker records (ticket.py fill), or from the
user's broker statement. If a position has shares but no lots, ask for the
purchase dates and costs. Never invent a cost basis.
The rules it applies (US federal, arithmetic only)
- Term: long term if sold more than one year after the purchase date,
otherwise short term.
report --lotsshows the date each lot turns long term. - Lot methods:
fifo(oldest first, what most brokers do by default),hifo(highest cost first) andspecific(named lots). The order sent to the broker does not carry lot ids: to sell specific lots the user must choose them in the broker's own tax-lot setting, or the broker uses its default method. - Wash sale: a loss is disallowed to the extent the same or a
substantially identical stock is bought within 30 days before or after the
sale. The tool checks the other lots still held, planned buys in
trader/orders.jsonand the loss sales it has logged. It cannot see an IRA, a spouse's account or another broker, and those count too. Say so.
Steps
- Refresh prices, then
lots.py report --lots. Show gains and losses by stock, and which lots are short or long term. - Before any sell (rebalance, a stop, a change of mind), run
lots.py sellwith the planned shares and method and show what it would realize. - For harvesting:
lots.py harvest --min-loss 100(and--min-pctif the user wants a percent threshold). For each candidate show the estimated loss, short and long term split, any wash-sale conflict, and the first day they could buy it back. Candidates with a conflict are not proposed. - Only if the user wants proposals:
harvest --write, then/trader-risk, then/trader-broker, one yes per order. - After a sale fills,
lots.py sell ... --recordupdates the lots and logs the realized result for the year.
Example: the reel's portfolio
The copy portfolio bought on 2026-10-13 (AAPL $1,250, AXP $1,119, GOOGL $823,
KO $708, BAC $600) has one lot per stock, all short term until 2027-10-14.
If BAC later trades below its $600 basis, harvest --min-loss 25 lists the
BAC-1 lot with its loss and "do not buy BAC again before" a date 31 days
after the sale. If the user also has a BAC buy planned in trader/orders.json,
it flags a wash sale instead of proposing the sell.
What it never does
It never files anything, never gives a tax rate or a tax bill, never tells the user what they owe, never places an order, and never proposes a harvest that it can see would be a wash sale.
Safety
- Not tax advice, and education and tooling, not financial advice. Check with a tax professional.
- Paper trading by default (
"paper": true). Going live is the user's own decision, in their own config. - Nothing in this pack places an order except trader-broker, and only when all three hold: trader-risk passed that exact order today, the user typed an explicit yes for that one order in the chat, and the user clicked Allow once on Claude's own card because the order tool is set to "Needs approval" (Customize > Connectors > tool permissions). Never set an order tool to "Always allow".
- No options, margin, short selling or leverage unless the config allows it and the user confirms.
- Broker keys live in environment variables or the Claude Desktop config, never in the chat.