The parts you reach for once it is running. For what it does and what it needs before you start, see How it works.
When collection is done, Clerk.AI drafts the email and stages the files — but you stay in control of what actually goes out, and the close isn't finished until your accountant is happy.
Clerk.AI writes the email in your accountant's language, with a summary and a chronological list of every attachment. Open Review email draft to read it. Want a change? Type or speak your feedback right there and the app revises the draft — nothing is sent behind your back.
Clerk.AI never sends on its own. You choose how it goes out:
The review panel lists every prepared attachment — click any one to open it and check it first. Then hit Show attachments in Finder: the folder opens with all the files already selected, so you drag them straight onto your email.
After you send, mark it sent — the close then waits on your accountant instead of showing as finished. When they reply, paste their response back into Clerk.AI. If they need more, ask Clerk to fetch it (a missing receipt, a reclassified line) and it revises the packet. Only when you're satisfied do you mark the books closed. Past closes track each state — ready to review, sent, closed — so you always know where a period stands.
The simplest way to capture a paper receipt is to photograph it — or AirDrop a receipt image to your Mac. Clerk.AI reads your photo library and runs Apple Vision OCR locally to pull the text out of each receipt, so the amounts, dates and vendors become searchable and available to match against your statements.
Because OCR runs on your Mac, receipt images are not uploaded to index them. This is how Clerk.AI finds receipts across a whole library without sending your photos anywhere.
Bookkeeping prep always has judgement calls — "is this lunch a client expense?", "is this subscription business or personal?". When Clerk.AI hits one, it shows a question card and you answer out loud.
Voice isn't only for question cards. Anywhere you talk to Clerk.AI — adding a note to a running close, or asking it to revise the email draft — you can hold to speak instead of typing.
From €5/month you also get the iPhone companion app, so you can answer these questions wherever you are — no need to be at the Mac.
Each of these has its own link, so the app can send you straight to the one you are in rather than to the top of this list.
Why: the session expired, or the bank wants a fresh strong-authentication step. This is the most common reason Clerk.AI stops, and it is not a fault: proving you are you is the one thing it cannot do on your behalf.
What to do: the browser window is already on the right page. Complete the sign-in and the 2FA prompt as you normally would, in that window, and the run picks up from where it stopped. It is your own login, running locally.
The same applies to any portal behind bank identification, not only banks. Brokers, exchanges and some supplier sites hit the same wall.
Why: the receipt was not in your mail or your photos, or its amount and date did not line up with the charge closely enough to be sure.
What to do: photograph or AirDrop the receipt so on-device OCR can index it, then let the close pick it up. You can also just say which one it is: a note like "the receipt for the Acme charge is the photo I took this morning" is enough for it to find and attach the right file.
A charge with nothing behind it is not dropped quietly. It is named in the letter to your accountant, so the worst case is that they see it flagged rather than missing.
Why: Photos access was refused, and macOS remembers a refusal indefinitely.
What to do: System Settings → Privacy & Security → Photos, and enable Clerk.AI. Worth checking even if you do not remember refusing: the prompt can arrive while you are looking at something else, and once dismissed it does not come back on its own. A large library then takes a while on its first pass, which is on-device OCR working rather than the app hanging.
Why: the microphone was not authorised.
What to do: System Settings → Privacy & Security → Microphone, and enable Clerk.AI. The app asks for this the first time you reach for the mic rather than during setup, so if you have only ever typed your answers, you will meet it the first time you try to speak one. Typing works everywhere speaking does.
Why: there is no AI connected. The agentic part needs Claude Code and your own Anthropic subscription or API key, which Clerk.AI drives on your behalf but does not pay for.
What to do: connect your Anthropic account in Settings. On-device OCR and transcription keep working regardless, so receipts carry on being indexed while you sort it out.
If a run was working and then stopped, this is probably not your problem — see the next one.
Why: your Anthropic account hit its usage limit mid-run.
What to do, in most cases, is nothing. Clerk.AI resumes by itself when the limit resets, and picks up where it stopped. Nothing is lost.
This is worth knowing about because it is the one stop with no question attached, so from the outside it looks exactly like working. If you want it moving sooner, that is a matter of your Anthropic plan rather than anything to change here.
Write to us. A person reads it, and if the answer belongs on this page it ends up here.