Choosing a file transfer service: eight questions worth asking
Every service takes a file and gives you a link, so the category looks interchangeable. The differences that matter are mostly not on the pricing page — here is what to compare, in the order the questions actually bite.
The file transfer category looks interchangeable from the outside. Every service takes a file, gives you a link, and charges somewhere between nothing and a few pounds a month. The differences that matter are mostly not on the pricing page.
This is what to compare, in the order the questions actually bite. If you would rather see the answers than work them out, we keep a side-by-side table of every major service with the same eight questions applied to each one.
1. Does the recipient need an account?
Start here, because it decides whether the tool is usable at all with people outside your organisation.
If your recipient has to sign up, sign in, install something, or request access, you are not sending a file — you are asking a favour, and roughly a third of the time you will end up emailing it anyway. Anything aimed at external clients should be: click, download, done.
2. Do links expire, and what does expired mean?
Two separate questions hiding in one.
First, is there an expiry at all, and can you choose it? A permanent link is a published file whether you meant it that way or not.
Second, and less obvious: when a link expires, is the file deleted or merely hidden? Plenty of services stop serving the link while the object sits in storage indefinitely. If the answer matters to you — and for anything sensitive it does — the privacy policy is where it is stated, not the feature list.
3. Can the provider read your files?
Almost every service says "encrypted". Most mean encrypted at rest with a key they hold, which protects against a stolen disk and nothing else.
End-to-end encryption means the file is sealed before upload with a key the service never receives. The reliable tell is recovery: if support can restore your file after you lose the key, they could always read it. Another tell is previews — a thumbnail of your document in a web dashboard means the server decoded it.
Neither is wrong. But you should know which one you have, because the marketing language is identical.
4. What actually happens at the size you send
Headline limits are easy to compare and slightly beside the point. What matters is behaviour at that size:
- Does a dropped connection cost you the whole upload, or one chunk?
- Do failed pieces retry by themselves?
- Does the progress figure move continuously, or jump once per chunk so a slow upload looks frozen?
- Is there a separate storage cap that ten small transfers will hit before any single one is large?
A service with a generous cap and a fragile upload is worse than a modest cap that never makes you start again.
5. Do you find out what happened?
"I sent it" and "they got it" are different claims. Worth having:
- Download counts, so you know it arrived — and can notice if it arrived more times than there are recipients.
- Delivery and open receipts when the service mails the link for you, which distinguishes a wrong address from a slow reply.
- Instant revocation, for the moment you realise it went to the wrong person.
6. Is it one message per recipient?
A small detail with real consequences. If a service mails your link to eight people in one message, all eight see each other's addresses. For a transfer going to several clients, competitors, or candidates, that is a disclosure you did not intend to make. Separate messages should be the default, not a setting.
7. What is the free tier really for?
Free tiers are either a genuine product or a demo. Signals of the first: a usable size limit without an account, expiry you control, and no advertising wrapped around the download page your client will see. Signals of the second: aggressive upsells on the recipient's screen, or a limit low enough that no real file fits.
Worth checking what the recipient sees, since that page represents you.
8. What does it look like?
Not vanity. When you send a client a link, the download page is a page with your name attached to it. A page carrying advertising, or a countdown pressuring them to sign up, is a page you are putting in front of someone you are trying to look professional to.
A short comparison sheet
| Question | Weak answer | Strong answer |
|---|---|---|
| Recipient account | Sign-in required | Click and download |
| Expiry | Permanent, or fixed | You choose, and it deletes |
| Encryption | "Encrypted" at rest | End to end, no recovery |
| Big uploads | Restart from zero | Chunked, auto-retry |
| Emailing the link | Everyone in one message | One message each |
| After sending | No visibility | Counts, receipts, revoke |
Where we stand
In the interest of being useful rather than coy: this site answers the right-hand column. No account for the recipient, expiry you choose that deletes the bytes, end-to-end encryption on by default with no recovery path, chunked uploads that resume, one message per recipient when we mail the link, and download counts with delivery receipts.
The honest limitations: there is no recovery if you lose an encryption key, there is no team billing or shared workspace, and for genuinely enormous archives a physical disk still beats any upload. If those are what you need, a different tool is the right answer, and knowing that now is better than finding out later.
Related: how to send large files, end-to-end encryption explained, and the plans.
