Alternatives · File Storage
Hightail alternatives
As of Nov 12, 2026, the highest-graded Hightail alternative is Dropbox (2.8 GPA). It's also the best free one. The catch, in its listing's words: "Basic plan: 2 GB to store and share files."
Hightail compared with 7 alternatives: WeTransfer, Dropbox, Box, ShareFile, Smash and 2 more.
Hightail has a free plan. Paid plans start at $12 per month, billed annually ($15 billed monthly). 6 of the 7 alternatives are free or have a free plan. One more offers a free trial.
Listings checked up to Nov 12, 2026 · Where the facts come from
Black Friday: is there a Hightail sale?
At a glance
| Tool | Price | Free plan | Runs on |
|---|---|---|---|
| HightailThis tool | Free plan · from $12/mo | Yes | Web, iOS |
| WeTransfer | Free plan · from $8/mo | Yes | Web, macOS, iOS, Android |
| Dropbox | Free plan · from $9.99/mo | Yes | Web, macOS, Windows, Linux, iOS, Android |
| Box | Free plan · from $5/mo | Yes | Web, macOS, Windows, iOS, Android |
| ShareFile | Free trial · from $16.50/mo | Trial only | Web |
| Smash | Free plan · from $6/mo | Yes | Web, macOS, iOS, Android |
| Filemail | Free plan · from $6/mo | Yes | Web, macOS, Windows, Linux, iOS, Android |
| Send Anywhere | Free plan · from $5.99/mo | Yes | Web, macOS, Windows, Linux, iOS, Android, Browser extension |
Price against what you get
Hightail starts at $12 a month and scores 2.3 out of 4 on features, ease of use and platforms. 6 of the 7 alternatives on this chart score higher and start lower: WeTransfer, Dropbox, Box, Smash, Filemail and Send Anywhere.
Features, ease of use and platforms, averaged
What paid plans start at, a month (each step along is roughly double) →
- The best score at each price
- Has a free plan
- No free plan
How each one differs from Hightail
WeTransfer
Send large files by email or link without recipient sign-up
- WeTransfer starts at $8 per month, billed monthly.
- WeTransfer also lists macOS and Android apps.
- WeTransfer also covers menu bar app.
Suits: Sending large files to clients who should not need an account
Dropbox
Cloud storage and file sync with transfer and signing tools
- Dropbox starts at $9.99 per month, billed yearly.
- Dropbox also lists macOS, Windows, Linux and Android apps.
- Dropbox also covers file sync.
Suits: Individuals who want 2 TB synced across Windows, Mac and Linux
Box
Business content storage with e-signatures, workflows and AI
- Box starts at $5 per user / month, billed annually (minimum 3 users).
- Box also lists macOS, Windows and Android apps.
- Box also covers workflow automation and file sync.
- Box does not cover documents, which Hightail does.
Suits: Companies that need unlimited storage priced per user
ShareFile
Secure file sharing and client portals for business teams
- ShareFile starts at $16.50 per user / month, billed annually ($18.15 billed monthly).
- ShareFile has no free plan, only a free trial, unlike Hightail.
- ShareFile lists no iOS app, which Hightail has.
- ShareFile also covers workflow automation and forms.
- ShareFile does not cover documents, which Hightail does.
Suits: Firms that exchange sensitive documents with clients
Smash
Browser-based file transfer with no sign-up and no paid size cap
- Smash starts at $6 per month, billed annually ($10 billed monthly).
- Smash also lists macOS and Android apps.
- Smash does not cover documents, which Hightail does.
Suits: One-off transfers where the recipient and sender skip accounts
Filemail
Large file transfer by email or link, free up to 5 GB
- Filemail starts at $6 per month, billed monthly.
- Filemail also lists Windows, macOS, Linux and Android apps.
- Filemail is end-to-end encrypted, according to its own site.
- Filemail does not cover documents, which Hightail does.
Suits: Sending files in the 5 GB to 250 GB range without a size cap worry
Send Anywhere
Send files by 6-digit key or link, with no sign-in on the free plan
- Send Anywhere starts at $5.99 per month, monthly billing.
- Send Anywhere also lists Windows, macOS, Linux and Android apps and a browser extension.
Suits: Moving files between your own phone and computer quickly
Limits worth knowing in Hightail
- The free Lite plan caps files at 100 MB and expires sends after 7 days.
- Online purchases are limited to 200 file-send recipients a day, and 100 per send on paid plans.
- Custom branding and Uplink are add-ons on Pro, Teams and Business rather than included.
- Teams covers 1 to 30 users and Business starts at 3 users; larger groups go through sales.
Common questions
What are the alternatives to Hightail?
The alternatives to Hightail in this directory are WeTransfer, Dropbox, Box, ShareFile, Smash, Filemail and Send Anywhere. Each one has a side-by-side comparison with Hightail.
Is there a free alternative to Hightail?
Yes. WeTransfer, Dropbox, Box, Smash, Filemail and Send Anywhere have a free plan alongside paid ones.
Which Hightail alternatives work on Windows?
The Hightail listing does not include a Windows app. Dropbox, Box, Filemail and Send Anywhere list one.
Which Hightail alternatives work on macOS?
The Hightail listing does not include a macOS app. WeTransfer, Dropbox, Box, Smash, Filemail and Send Anywhere list one.
When were these prices checked?
Each listing shows its own date. On this page they run from Oct 5, 2026 to Nov 12, 2026. Vendors change prices without notice, so confirm on their site before you buy.