Receipts, filed as they arrive instead of every April
Nobody files receipts in March. The work is always done in a single miserable session, months later, from an inbox that has moved on.
How do you organise receipts from email before tax season?
Stop treating it as a March job. Write one rule describing the receipts you get — travel, software, supplies — and they get filed the week they arrive, named by merchant and date. By the time your accountant asks, the folder is already complete instead of needing a weekend of archaeology.
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File them the week they arrive, not in March
A receipt is easiest to identify the day it lands, while you still remember the trip or the purchase. Months later you are reconstructing context from a filename someone else chose.
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Let the merchant and date come from the receipt
Names are rebuilt from the document's contents, so the folder sorts by merchant and date on its own. That is what makes a year's receipts reviewable instead of just present.
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Watch the 3 KB floor on tiny images
Attachments under 3 KB are skipped before classification, which throws away signature graphics and tracking pixels. A genuinely tiny receipt image can be dropped too — if one never appears in History, check its size first.
Why this category rots quietly
Receipts do not feel urgent when they arrive. Each one is a small confirmation of something already paid, so it stays in the inbox, and the pile grows quietly for eleven months without ever demanding attention.
They are also the messiest category technically. A receipt mail often carries three or four attachments where only one is the receipt — the rest are logos, signature images and social icons — and the receipt itself may be a 40 KB image rather than a tidy PDF.
What the April session actually costs
The annual catch-up is the most expensive way to do this, and not because of the hours. It is done under deadline, from memory, against an inbox where search terms have stopped being obvious — and the receipts that cannot be found within a few minutes simply stop being claimed.
That is the real number: not the afternoon, but the deductions quietly abandoned because reconstructing the paperwork cost more than the deduction was worth.
Sorting by what you will do with it in April
Receipts are worth splitting by their eventual use rather than by vendor, because in April the question is never “who sold me this” — it is “can I claim it”.
“Receipts”
Every business on earth calls its confirmation email a receipt, so this collects parking, software renewals and client dinners into one undifferentiated folder.
“Receipts for travel and client meals that I will claim as expenses. Not personal shopping, not subscription renewals.”
Splits by what you will do with the document at tax time, which is the only distinction that matters when the folder is finally opened.
What a filed receipt looks like
Vendor and date are read off the receipt, whether it arrived as a PDF or as a photo:
Receipt_Renfe_2026-05-19.pdf
It goes to Expenses Travel 2026. Twelve months of that produces a folder sorted by date without anyone having sorted anything, which is the state you want it in when the deadline arrives.
Attachments under 3 KB are skipped before anything is classified. That threshold exists to throw away signature graphics and tracking pixels, and it works — but it also means a genuinely tiny receipt image can be discarded silently. If a receipt you expected never shows up in History, its size is the first thing to check.
Questions about receipts and expenses
Will it catch receipts already sitting in my inbox?
No. The connection works forward from the day you set it up, so this year's backlog stays a manual job. Connecting in January rather than April is most of the value.
What about receipts that are just HTML in the message body?
Those cannot be filed — there is no attachment. Many services have a setting to attach a PDF copy instead, and switching it on is worth the two minutes per vendor.
Can I keep personal and business receipts apart?
Yes, by pointing a rule at one specific mailbox. A rule restricted to your work address will not see anything that arrives in your personal one, even though both are connected.
Related questions
Every invoice filed, without opening the mail
The category with the most senders, the least consistent subject lines, and the highest cost when one goes missing. Read it →
Save Gmail attachments to Google Drive, automatically
Gmail routes envelopes. It has never been able to route what is inside the attachment — which is the part you actually want filed. Read it →
Move Outlook attachments into OneDrive without a flow
Microsoft already ships an automation tool for this. It is worth being precise about where it stops being the cheaper option. Read it →
The cheapest month to start is this one.
Nothing is retroactive, so every month you wait is a month you will do by hand later.