Can ChatGPT or Gemini Do My Taxes From Bank Statements?

It's a fair question, and the honest answer is: for some things, yes — and for preparing your actual tax report, you probably shouldn't. Here's the difference, plainly.

What a chatbot is genuinely good at

We'd be lying if we said AI assistants weren't useful for tax questions. They are. A chatbot is a good place to:

• Ask what a T2125 or Schedule C line means
• Understand whether a type of expense is generally deductible
• Get a quick read on a single confusing transaction
• Learn how home office or vehicle deductions work before you tackle them

If that's what you need, use one. Heightly's own reports assume you'll check things against CRA and IRS guidance, and an assistant is a reasonable way to do that.

Where it goes wrong: doing the whole year

Preparing a tax report from your statements isn't a question — it's a few hundred small decisions plus arithmetic that has to hold together. That's where the chatbot approach breaks down, for reasons that don't show up until you've already trusted the output.

1. Your bank statements are the most sensitive documents you have

A year of statements shows where you live, where you sleep, who pays you, what you owe, and everything in between. Before pasting that into a consumer chatbot, it's worth actually reading its data retention and training policy — most people never do. Some assistants use uploaded content to train future models unless you find and change a setting; some retain it in ways you can't audit or delete.

Heightly is built around the opposite assumption: statements are radioactive. Uploaded files are deleted 90 days after your report is delivered, reports are deleted after 12 months, you can delete everything earlier yourself, and nothing you upload is used to train anything. That's in our privacy policy in plain terms — and it's the kind of policy you should demand from anyone you hand a year of statements to, including us.

2. A year of transactions doesn't fit

A real year of sole-proprietor banking is several hundred to a couple of thousand transactions across many statements. Chatbots process what fits in their working memory, and when your data exceeds it they don't stop — they quietly work with what fits. Rows get dropped, months get summarized, and the output still looks complete. Nothing warns you that March is missing.

Heightly parses every file, counts every transaction, and shows you the count — up to 2,000 transactions across 26 files, checked against your statements, with duplicates across files detected and excluded. If something can't be read, you're told, not skipped.

3. The totals have to foot — and nobody checks a chatbot's math

A tax report's numbers must reconcile: categories sum to totals, GST/HST ties across sections, the same figure matches everywhere it appears. Language models are famously unreliable at exactly this — long columns of arithmetic — and the failure is silent. The total looks plausible. Nobody adds up 300 rows to check.

Heightly's arithmetic is computed, not generated. Category totals cross-foot to the summary, the GST/HST section reconciles to the expense table, and that reconciliation is enforced by automated tests on every change we ship. When we find drift beyond rounding, that's a bug we fix — not a "language models do that sometimes."

4. Ask twice, get two answers

Here's something we learned building Heightly's own AI categorization: a model asked to categorize the same transaction in two different batches can give two different answers. We found identical government tax payments categorized two different ways in one report — and we had to build dedup machinery so every identical transaction is decided exactly once and the answer applied consistently.

A chat conversation has none of that. Paste your statements in two sessions — or even ask again in the same one — and categories shift. Which answer goes on your return?

5. You get a paste-back, not a report

What comes out of a chat is text in a window. What your accountant — or your tax software — wants is an organized report: income and expenses by tax line, capital assets listed separately, vehicle and home office worksheets, the transaction detail behind every number, and notes on anything that needs a decision. Heightly produces that as a PDF and an Excel file that are yours to keep, from a repeatable process that produces the same answer tomorrow.

The honest summary

	A chatbot	Heightly
Explaining a tax concept	Great	Not what it's for
One confusing transaction	Good	Works, but overkill
A full year, hundreds of transactions	Silently incomplete	Counted and checked
Arithmetic	Plausible-looking	Reconciled and tested
Same input, same answer	Not guaranteed	By construction
Your statements afterwards	Depends on a policy you haven't read	Deleted on a schedule you can see
Output	Text in a chat window	PDF + Excel your accountant accepts

Frequently asked questions

Can I upload my bank statements to ChatGPT to do my taxes?

You can, but a full year of transactions typically exceeds what a chatbot reliably processes — rows can be silently dropped, arithmetic is generated rather than computed, and the same transaction can get different categories on different runs. Chatbots are useful for individual tax questions; a full-year report needs counted, reconciled output.

Is it safe to put bank statements into an AI chatbot?

Read the retention and training policy first. Some assistants retain uploads or use them for training unless a setting is changed. Bank statements reveal nearly everything about your life, so any tool you give them to should publish a deletion schedule you can verify.

Where Heightly draws its own line

Fair is fair: Heightly is software, not a bookkeeping service, an accounting firm or a tax preparer. It doesn't file your return and it doesn't give tax advice — your report is a draft organizer to review yourself or with your accountant before filing. It's built for unincorporated sole proprietors in Canada (excluding Quebec) and the United States, and it isn't the right tool for corporations or for very high transaction volumes.

And the free preview needs no payment details: upload a single statement and watch it categorize your own transactions before deciding anything.

Try the free preview →