Hightail vs Send Anywhere (2026): which should you pick?
As of Nov 12, 2026, Send Anywhere grades higher than Hightail: 2.8 against 2.2 out of 4.0.
Checked Nov 12, 2026 · graded Nov 12, 2026 by ToolGPA
Send Anywhere grades higher on the free plan, ease of use and platforms. They get the same grade on value for money and features.
Price, platforms and features side by side. The table says where each price was read and when.
Hightail
Large-file sharing with creative review and project tracking
Send Anywhere
Send files by 6-digit key or link, with no sign-in on the free plan
Which one is for you
Pick Hightail if
- Fits if you send big creative files and want comments on them
- Works for freelancers who can live with 2 GB free
Look elsewhere if
- Tight if you send big files free: Lite stops at 100 MB a file and links expire in 7 days
- Pricey if you pay monthly: Pro is $15 against $144 for the year
- Watch out: custom branding and Uplink are add-ons, not included on Pro, Teams or Business
- Watch out: Teams covers 1 to 30 users and Business starts at 3, so larger groups go to sales
Pick Send Anywhere if
- Fits if you send files between your own devices and want no sign-up
- Works for someone sending one-off files over 10 GB
Look elsewhere if
- Tight if you share links for days: free links expire after 48 hours
- Skip it if you want storage, as it only transfers
- Watch out: paid plans are sold as an Email add-on and cap transfers at 20 GB or 30 GB
- Watch out: the plan table doesn't say which plans include encryption or passwords
How we grade them
| 2.2GPAHightailFair | 2.8GPASend AnywhereGood | |
|---|---|---|
| Value for money | CPro at $12 a month billed annually ($15 monthly) sits in the dearer quarter of the category but under its $16.50 dearest-tenth line. | CThe Email add-on is $5.99 a month for Lite, between the category's $3.99 and $6.95 marks. |
| Free plan and trial | CLite is free with 2 GB, files up to 100 MB, 7-day links and limited previews. | BFree: no sign-in, 1:1 live transfers up to 50 GB and links up to 10 GB that expire after 48 hours. |
| Features | CSending, review and project tracking are covered, but custom branding and Uplink are add-ons and sending is capped at 100 recipients a send. | CSending by key or link works, but it is transfer only, not storage, and paid plans cap size at 20 GB or 30 GB. |
| Ease of use | CNo store rating on record, and review and project features to learn. | BNo store rating on record, but there is nothing to set up: pick a file and get a key. |
| Platforms and integrations | BWeb and an iPhone app, with 7 integrations listed and no desktop app. | AWeb, Windows, Mac, Linux, iPhone, Android and browser extension, with 2 integrations. |
| Best for | sending files and getting creative work reviewed | sending a file with a 6-digit key |
The GPA is the average of the five grades: an A is 4 points, an F is none. The full reasons are on each tool's page: Hightail and Send Anywhere. How we grade
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. Send Anywhere starts at $5.99 a month and scores 3.0.
Send Anywhere scores higher and starts $6.01 a month lower. Of the other file storage and sync services on the chart, 22 score higher than Hightail for less, and 6 score higher than Send Anywhere for less.
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
Where they differ
At a glance
| Hightail | Send Anywhere | |
|---|---|---|
| Pricing | Free plan | Free plan |
| Starts at | $12 per month, billed annually ($15 billed monthly) | $5.99 per month, monthly billing |
| Free plan | Lite: 2 GB storage, files up to 100 MB, send links expire after 7 days, limited previews, and 30 recipients per send. | Free: 1:1 real-time transfers up to 50 GB and links up to 10 GB; links expire after 48 hours. |
| Free trial | None listed | None listed |
| Web | ||
| macOS | ||
| Windows | ||
| Linux | ||
| iOS | ||
| Android | ||
| Browser extension | ||
| Made by | Open Text Corporation | Rakuten Symphony Korea, Inc. |
| Price read from | hightail.com | send-anywhere.com |
| Checked | Nov 12, 2026 | Nov 12, 2026 |
Worth knowing
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.
Send Anywhere
- Free links stop at 10 GB and expire after 48 hours.
- The pricing page was read on its monthly toggle; yearly billing prices were not shown.
- Paid plans are sold as an Email add-on, and cap transfer size at 20 GB (Lite) or 30 GB (Standard).
- The plan table does not say which plans include data encryption or password setting.
Key features
Hightail
- Large file sending
- Send limits are 100 MB on Lite, 25 GB on Pro, 50 GB on Teams and 500 GB on Business, with send tracking and delivery notifications on paid plans.
- Expiry and passwords
- Lite sends expire after 7 days. Paid plans can set an expiration date or keep files indefinitely, and add password protection.
- Precise comments
- Reviewers can comment on a specific point in a file. Teams and Business add version control and side-by-side version comparison.
- Project management
- Teams and Business include to-dos, advanced approval routing and personal and team dashboards for creative projects.
- Adobe and cloud integrations
- Photoshop and Illustrator plugins are listed on every plan, along with syncing from Dropbox, Google Drive and OneDrive.
Send Anywhere
- Six-digit key transfers
- A key is generated after you pick files; entering it on the receiving device starts a direct transfer without an account.
- Share links
- Links can be shared with several people. Free links expire after 48 hours; paid plans can set custom or unlimited expiry.
- Cross-platform apps
- Android, iOS, Windows, macOS and Linux apps are listed, plus Chrome and Whale browser extensions.
- Email add-on
- Paid plans send large files from Gmail in Chrome and from Outlook through extensions, with link management.
- Download page customization
- Lite lets you set the wallpaper on the download page, and Standard also lets you place your own link on it.
- Password and download controls
- The plan table lists password setting, custom download counts, download notification emails and data encryption.
Plans
Hightail
Lite$0
2 GB storage, 100 MB files, 7-day expiry, limited previews and precise comments.
Pro$12
per month, billed annually ($15 billed monthly)
Unlimited storage, 25 GB files, configurable expiry, password protection and 5 nested folders.
Teams$24
per user / month, billed annually ($30 billed monthly)
1 to 30 users, 50 GB files, version control, approval routing, dashboards and phone support.
Business$36
per user / month, billed annually ($45 billed monthly)
For 3+ users: 500 GB files, 30 nested folders, enterprise-grade security and a dedicated support team.
Send Anywhere
Free$0
1:1 real-time transfers up to 50 GB, links up to 10 GB, 48-hour link expiry.
Email Add-on Lite$5.99
per month, monthly billing
Downloads up to 200 GB, 20 GB transfer limit, faster servers and 2 GB of unlimited-link storage.
Email Add-on Standard$9.99
per month, monthly billing
Downloads up to 500 GB, 30 GB transfer limit, faster servers and 5 GB of unlimited-link storage.
Ways to pay less
Hightail
- Annual discount
Roughly 20% off with annual billing
The pricing FAQ gives Pro at $144 a year, Teams at $288 per user and Business at $432 per user, and says annual billing saves about 20% a month.
Send Anywhere
No public discounts listed.
Common questions
Which is cheaper, Hightail or Send Anywhere?
As of Nov 12, 2026, Send Anywhere is cheaper to start with: $5.99 a month, against $12 a month for Hightail. Hightail starts at $12 per month, billed annually ($15 billed monthly), and Send Anywhere starts at $5.99 per month, monthly billing.
Which has a free plan, Hightail or Send Anywhere?
As of Nov 12, 2026, both Hightail and Send Anywhere have a free plan.
Which platforms do Hightail and Send Anywhere run on?
As of Nov 12, 2026, only Send Anywhere lists macOS, Windows, Linux and Android apps and a browser extension. Both list a web app and an iOS app. A platform missing from a listing is one its maker's pages did not mention.
More comparisons
How this page was made
- The verdict at the top follows a fixed rule. When both tools are in the same category and either is in our top three for it, the verdict follows that ranking: the higher-placed tool is our pick. The top three weigh who each tool suits as well as its grades, so a pick can go against the GPA. Otherwise the page does not pick one and says which grades higher: the higher GPA first; on a tie, the one with a free plan, then the one that starts cheaper in dollars a month, counted the same way for both; if they are still level, what the choice depends on.
- The grades are our own, from each tool’s review or report card. The GPA is their average.
- Prices, plans and platforms come from each tool’s listing. The table above says where each price was read and when.
- The differences and the answers to the questions are worked out from those listings.