We’re proud to introduce Files, a feature that lets us fully organise the paperwork that our financial lives keep generating.
Whether you’ve been attaching receipts with Attachment Inbox, or you’re just looking for somewhere sensible to keep the household’s important documents, Files is now ready for you.
The monthly power bill in your inbox. The receipt for the dishwasher that the warranty requires. The plumber’s invoice. The car insurance policy. The photo of a receipt you snapped in a car park before it faded to nothing. That vet bill.
You’ve been keeping these documents because you suspect you’ll need them at some point, and yet none of them live anywhere near your money. They’re stranded in iCloud, Google Photos, Drive, and Dropbox. You have ample storage, but retrieval is a pain.
And if you’re the Household CFO, well you’re probably the only one who knows where anything is — so nothing can be found when you’re not around.
This is the problem we’re solving with Files.
Files isn’t trying to replace cloud storage, but what it does do is put your files in context. Paired with PocketSmith’s ability to attach files to transactions and budgets, here’s a quick summary of what’s new:
Your financial records, all in one place.
This is one of the biggest changes under the hood.
Previously, an attachment could only belong to a single transaction. Now, a file can be attached to multiple transactions, multiple budgets, or both.
Upload an insurance policy once and attach it to the premium payments and the budgets it relates to. Mark it as “Important” and add a “Premiums” label to it to find it in the Files area. We’ve made it as easy as possible to locate important documents.
And importantly, removing a file from a transaction or budget no longer deletes it. You’re simply removing the link. The file remains safely stored in your library until you deliberately delete it.
Financial lives generate more than PDFs, so Files accepts a much broader range of formats.
Documents, spreadsheets, images, PDFs, and even videos are all supported. That includes DOCX, OpenDocument, Markdown, CSV, XLSX, ODS, PNG, JPEG, GIF, HEIC, MOV, MP4, and more.
A short video clip for insurance purposes is just as welcome as a coffee receipt.
A storage indicator shows exactly how much space you’re using, with room to grow as your needs do:
Back in 2020, we leaned into a tool we all use: email. We called this the Attachment Inbox, and thanks to Files, it’s now better than ever.
Today, the Files Inbox gives every account a private, secure email address. Forward a utility bill, email yourself a photo of a receipt, or set up a Gmail filter to automatically forward attachments, and the document will land inside PocketSmith ready to be assigned.
Keep documents organised with previews, custom names, descriptions and labels, plus a complete view of where they’re attached.
Attaching a receipt to a transaction isn’t unheard of in personal finance software, but a true document library that lives alongside your money is unique.
| App | How it handles files | Central library? |
|---|---|---|
| Monarch Money | Attach files and scan receipts, but each stays tied to its transaction (max 3 images; PDFs on web only). | No |
| Quicken Simplifi | Attach photos, scans, or PDFs to a transaction, kept as long as the transaction exists. | No |
| Quicken LifeHub | A dedicated document vault — but a separate product/add-on, disconnected from your transactions. | Standalone, not linked |
| YNAB | No native attachments; users rely on third-party add-ons and cloud-storage workarounds. | No |
| Copilot / Rocket Money | No native receipt or document attachment to transactions. | No |
| PocketSmith | First-class Files page: email in, upload anything, label, star, mark important, one file linked to many transactions and budgets. | Yes — and linked to your money |
PocketSmith is the only product that gives you a proper library and a living link between each document and the money it represents. Payments and paperwork finally live together.
If you’re the person who runs your household’s finances, Files can be one of the most useful things we’ve shipped.
Now you can make the household more resilient. With Files, the knowledge stops living entirely inside one person’s head. Let’s get started.
Jason is the CEO and co-founder here at PocketSmith. He is fascinated by our unique relationships with our money, and is passionate about making peoples’ lives better through the technologies we craft. He’s been a sneakerhead since the 80’s, and loves gardening on sunny days while listening to Planet Money.
