Box vs Hightail (2026): which should you pick?
As of Nov 12, 2026, Box grades higher than Hightail: 2.8 against 2.2 out of 4.0.
Checked Oct 5, 2026 and Nov 12, 2026 · graded Oct 10, 2026 and Nov 12, 2026 by ToolGPA
Box grades higher on features, ease of use and platforms. Hightail grades higher on value for money. They get the same grade on the free plan.
Price, platforms and features side by side. The table says where each price was read and when.
Box
Business content storage with e-signatures, workflows and AI
Hightail
Large-file sharing with creative review and project tracking
Which one is for you
Pick Box if
- Fits if your company wants unlimited storage priced per user, from 3 users up
- Works for teams that send contracts for signature from where they're stored, or plug files into Microsoft 365, Salesforce or Slack
Look elsewhere if
- Skip it if you're one person wanting more space, as every paid plan priced here needs at least 3 users
- Pricey if you want the unlimited storage and the AI, which start at $15 a user against a $5 category middle
- Not for you if you're on Linux, since Box Drive is Mac and Windows only
- Tight if you stay free: 10 GB, no file over 250 MB, 1 version kept and 5 signature requests a month
- Watch out: uploads cap at 2 GB on Starter and 5 GB on Business, and Enterprise Plus is billed yearly only
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
How we grade them
| 2.8GPABoxGood | 2.2GPAHightailFair | |
|---|---|---|
| Value for money | DStorage in this category has a middle price of $5 a month, and the dearest tenth starts at $9.99. Box's entry plan is $5 a user but needs 3 users, so $15 a month minimum for 100 GB. The parts people actually come for, unlimited storage, Box AI and unlimited signing, start at $15 a user. | 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. |
| Free plan and trial | CFree for one person with 10 GB, which sounds fine until you read the caps: no file over 250 MB, 1 version kept of anything you edit, 5 signature requests a month. A phone video can breach that upload limit. | CLite is free with 2 GB, files up to 100 MB, 7-day links and limited previews. |
| Features | BStorage and sharing, plus Box Sign for e-signatures, workflow automation and Box AI, with Box Drive opening files on a Mac or PC without filling the disk. The listing's own upload ceilings, 250 MB free and 2 GB on Starter, keep it off an A. | CSending, review and project tracking are covered, but custom branding and Uplink are add-ons and sending is capped at 100 recipients a send. |
| Ease of use | A4.8 from about 191,000 App Store ratings. On a computer, Box Drive puts your Box files in Finder or Explorer, so there's nothing new to learn. | CNo store rating on record, and review and project features to learn. |
| Platforms and integrations | AWeb, Mac, Windows, iPhone and Android, and Box counts more than 1,500 connected apps, Microsoft 365, Salesforce and Slack among them, with API call allowances on the paid plans. No Linux app, mind. | BWeb and an iPhone app, with 7 integrations listed and no desktop app. |
| Best for | company files with signing and workflows built in | sending files and getting creative work reviewed |
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: Box and Hightail. How we grade
Price against what you get
Box starts at $5 a month for each person and scores 3.7 out of 4 on features, ease of use and platforms. Hightail starts at $12 a month and scores 2.3.
Box scores higher and starts $7 a month lower. Of the other file storage and sync services on the chart, none scores higher than Box for less, and 22 score higher than Hightail 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
- Box also covers workflow automation and file sync.
- Hightail also covers documents.
At a glance
| Box | Hightail | |
|---|---|---|
| Pricing | Free plan | Free plan |
| Starts at | $5 per user / month, billed annually (minimum 3 users) | $12 per month, billed annually ($15 billed monthly) |
| Free plan | Individual plan: one user, 10 GB of storage, a 250 MB file upload limit, 1 file version and 5 Box Sign requests per month. | Lite: 2 GB storage, files up to 100 MB, send links expire after 7 days, limited previews, and 30 recipients per send. |
| Free trial | Free trial offered on Business Starter, Business, Business Plus, Enterprise and Enterprise Plus | None listed |
| Web | ||
| macOS | ||
| Windows | ||
| iOS | ||
| Android | ||
| Made by | Box, Inc. | Open Text Corporation |
| Price read from | peony.ink (not the vendor's own page) | hightail.com |
| Checked | Oct 5, 2026 | Nov 12, 2026 |
Worth knowing
Box
- Business and Enterprise plans require a minimum of 3 users.
- File upload size is capped by plan: 250 MB on the free plan, 2 GB on Business Starter, 5 GB on Business and 15 GB on Business Plus.
- Enterprise Plus is sold on annual billing only, and Enterprise Advanced is priced through sales.
- The downloads page lists Box Drive for Mac and Windows only, with no Linux app.
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.
Key features
Box
- Box Drive
- A desktop app for Mac and Windows that opens Box files from the computer without taking up much local disk space.
- Box Sign
- E-signatures are built in: 5 signature requests a month on the free plan, 10 on Business Starter, and unlimited from the Business plan up.
- Box AI
- Box AI is included from the Business plan. Enterprise adds 1,000 AI Units a month and Box Hubs, and Enterprise Plus raises the allowance to 2,000.
- External collaboration
- The Business plan charges for each external collaborator, while Business Plus and the Enterprise plans allow an unlimited number.
- File version history
- The free Individual plan keeps 1 version of each file, Personal Pro keeps 10 and Business Starter keeps 25.
- Integrations and API
- Box lists more than 1,500 apps and AI agents that connect to it, and paid business plans include a monthly allowance of API calls.
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.
Plans
Box
Individual$0
Single user with 10 GB of storage, a 250 MB file upload limit and 5 Box Sign signature requests per month.
Business Starter$5
per user / month, billed annually ($7 billed monthly)
Minimum of 3 users: 100 GB of storage, 2 GB file uploads, 25 file versions and 10 Box Sign requests per month.
Business$15
per user / month, billed annually ($20 billed monthly)
Minimum of 3 users: unlimited storage, 5 GB file uploads, Box AI, unlimited e-signatures and 50,000 API calls per month.
Business Plus$25
per user / month, billed annually ($33 billed monthly)
Minimum of 3 users: unlimited storage, 15 GB file uploads and unlimited external collaborators.
Enterprise$35
per user / month, billed annually ($47 billed monthly)
Minimum of 3 users: 50 GB file uploads, 1,000 AI Units per month, Box Hubs and 100,000 API calls per month.
Enterprise Plus$50
per user / month, annual billing only
Minimum of 3 users: 150 GB file uploads, 2,000 AI Units per month and support with 24-hour coverage.
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.
Ways to pay less
Box
- Annual discount
About 25% lower with annual billing
Box's pricing page has a monthly or annual toggle that advertises a saving for paying annually. The listed prices put Business at $15 per user annually against $20 monthly.
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.
Common questions
Which is cheaper, Box or Hightail?
As of Nov 12, 2026, Box starts at $5 per user / month, billed annually (minimum 3 users), and Hightail starts at $12 per month, billed annually ($15 billed monthly). One is priced for each person and the other is not, so which costs less depends on how many of you use it.
Which has a free plan, Box or Hightail?
As of Nov 12, 2026, both Box and Hightail have a free plan.
Which platforms do Box and Hightail run on?
As of Nov 12, 2026, only Box lists macOS, Windows and Android apps. 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.