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Accounting, 280E, and QuickBooks: Where AI Helps (and Where It Can't)

280E means the cost of the product is about the only thing you can deduct, so which bucket each expense lands in is worth real money. AI can sort a month of transactions with a reason for each. It cannot be your accountant, and it does not sign anything.Under 280E only cost of goods survives, so every transaction needs a bucket every month. A model does the first sort into a 280E-aware chart of accounts with a reason and a confidence per line; your CPA reviews the allocations and signs. Plus the QuickBooks purchase-order-versus-bill ask, which is an automation, not AI.IRC §280E: only COGS survives. LLM classifies transactions into a COGS-aware chart of accounts with reason and confidence; low-confidence, SPLIT and UNSURE rows queue for the CPA monthly. The QBO PurchaseOrder-vs-Bill request is a deterministic sync with an idempotency marker, no model.

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what can a cannabis business actually deduct under 280E?what can a cannabis business actually deduct under 280E?what survives 280E?
280E is one sentence of federal law: no deduction or credit for a business trafficking in Schedule I or II substances. Cost of goods sold is not a deduction, it is subtracted before you reach income, so it survives. What counts as cost of goods for a retailer versus a grower, under which accounting method, is the argument your CPA is paid to have. None of this is tax advice.280E is one sentence of federal law: no deduction or credit for a business trafficking in Schedule I or II substances. Cost of goods sold is not a deduction, it is subtracted before you reach income, so it survives. What counts as cost of goods for a retailer versus a grower, under which accounting method, is the argument your CPA is paid to have. None of this is tax advice.IRC 280E disallows deductions and credits for trafficking in Schedule I or II substances; COGS is not a deduction but a reduction of gross receipts, so it survives. The scope of COGS by license type and inventory-costing method is a CPA determination, not a prompt's. Compliance-required spend is not automatically COGS.
can AI categorize my cannabis expenses for 280E?can AI categorize my cannabis expenses for 280E?where does an LLM fit in 280E bookkeeping?
It can do the first pass. Give it your own list of accounts and a month of transactions and it proposes a bucket per line, with a reason that quotes the transaction and a number for how sure it is. Sort by that number and the doubtful lines, plus anything marked split or unsure, become your CPA's review list. It does not decide what is deductible and it does not sign anything.It can do the first pass. Give it your own list of accounts and a month of transactions and it proposes a bucket per line, with a reason that quotes the transaction and a number for how sure it is. Sort by that number and the doubtful lines, plus anything marked split or unsure, become your CPA's review list. It does not decide what is deductible and it does not sign anything.First-pass classification into a COGS-aware chart of accounts, returning account code, reason and confidence per line, batched with the chart pasted every time and no memory across months. Low-confidence, SPLIT and UNSURE rows queue for CPA review, and bucket totals are verified in a spreadsheet, never read off the model's own summary. Observed failure: a whole payroll run assigned to COGS, because job titles are not in the ledger.
why do my purchases arrive in QuickBooks as bills instead of purchase orders?why do my purchases arrive in QuickBooks as bills instead of purchase orders?PurchaseOrder versus Bill on a QuickBooks sync
Because a Bill is what you owe and posts to what you have payable, while a Purchase Order is only an intention to buy and changes no balance. When a delivery lands and the purchase is recorded, the books need the Bill, which is why the sync creates it. Wanting the PO stage first is a small automation job, not an AI one.Because a Bill is what you owe and posts to what you have payable, while a Purchase Order is only an intention to buy and changes no balance. When a delivery lands and the purchase is recorded, the books need the Bill, which is why the sync creates it. Wanting the PO stage first is a small automation job, not an AI one.A QuickBooks PurchaseOrder is non-posting; a Bill posts to accounts payable, which is why a purchase sync creates the Bill. To get the PO stage, create the PO on each new purchase and write its id back as an idempotency marker, then let the Bill follow on receipt. Watch two failure modes: a vendor that does not exist in QuickBooks yet, which the job should map or create rather than invent, and a re-run without the marker, which doubles every PO.

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