Files isn’t trying to replace your cloud storage — it puts your documents in context, right beside the transactions and budgets they explain. Read the launch post »
Browse, upload, preview, rename, describe and download your documents — all from a single place.
Organize files with labels and drill down from the sidebar, just like Finder or Explorer.
Flag the documents you’ll rely on for years — insurance policies, mortgage papers, legal documents.
A temporary nudge for things in flight. Waiting on a refund or a claim? Star it, deal with it, clear it.
Attachments used to belong to a single transaction. Now one file can be attached to multiple transactions, multiple budgets, or both.
Upload an insurance policy once and link it to every premium payment and the budget it covers.
Removing a file from a transaction or budget only removes the link. The file stays in your library until you delete it.
Search by date, label and file type to pull up any invoice — along with the transaction it’s attached to.
Each file shows everywhere it’s attached, so the paperwork and the payments always agree.
Financial lives generate more than paperwork. A video walkthrough for insurance is just as welcome as a coffee receipt.
Attaching a receipt to a transaction isn't unheard of. A true document library that lives alongside your money is.
| App | How it handles files | Central library? |
|---|---|---|
| Monarch Money | Files stay tied to a single transaction; max 3 images, PDFs on web only. | No library |
| Quicken Simplifi | Attachments live and die with their transaction. | No library |
| Quicken LifeHub | A document vault — but a separate add-on, disconnected from your transactions. | Not linked |
| YNAB | Photos only, tied to a single transaction; no PDFs or documents. | No library |
| Copilot / Rocket Money | No native receipt or document attachment. | No library |
| PocketSmith | First-class Files page: email in, upload anything, label, star, mark important — one file linked to many transactions and budgets. | Linked library |
If you’re the person who runs the household’s finances, Files means the knowledge stops living entirely inside one person’s head.
Label deductible receipts and statements tax-2026 through the year, then pull them all up in one search when it’s time to file.
The receipt and warranty live on the appliance’s actual transaction — proof of purchase is one click away when it fails in year three.
Upload photos or a video walkthrough of your contents and mark them important — exactly what insurers ask for after a fire or burglary.
Prescriptions, invoices and rebate letters attached to their payments make reimbursement painless.
Waiting on a refund before you finalize a return? Star the document, then clear it once the money moves.
Insurance, mortgage and legal documents marked important mean a partner can find what matters, even when you’re not there.
A storage indicator shows exactly how much space you’re using — and Files is included on every plan. Compare plans & pricing
250MB — Get started
3GB — Everyday paperwork
15GB — The whole household
50GB — Everything, forever
Files is a document library built into PocketSmith. It stores your bills, receipts, invoices, insurance policies and other financial documents alongside your money, so each file can be linked to the transactions and budgets it belongs to.
Documents, spreadsheets, images, PDFs and video — including DOCX, OpenDocument, Markdown, CSV, XLSX, ODS, PNG, JPEG, GIF, HEIC, MOV, MP4 and more. See the full list of supported file types.
It grew up! The Attachment Inbox is now the Files Inbox — better than ever, and connected to your full document library.
Read the Files launch post for the full story, or head to the Learn Center for the Files overview and a guide to attaching files to transactions.
Yes — a single file can be attached to multiple transactions, multiple budgets, or both. And removing a file from a transaction only removes the link; the file stays safely in your library until you deliberately delete it.
Yes. 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 an email filter to forward attachments automatically.
Storage scales with your plan: 250MB on Free, 3GB on Foundation, 15GB on Flourish, and 50GB on Fortune.
Take control of your finances today.
Start free, or check out Plans & Pricing »
Getting started is easy! Use our Express Migration tool to easily bring over all your accounts, transactions and categories.
Invite another PocketSmith user - be it an advisor, friend or family member - to access and manage your account.
Secure your account by requiring a code from your mobile phone along with your username and password.
Set up your dashboards and finances in the way that makes sense, and get email summaries of your financial activity sent at a schedule you choose
