Box vs Kiteworks (2026): which should you pick?
As of Nov 13, 2026, Box grades higher than Kiteworks: 2.8 against 2.0 out of 4.0.
Checked Oct 5, 2026 and Nov 13, 2026 · graded Oct 10, 2026 and Nov 13, 2026 by ToolGPA
Box grades higher on the free plan, features, ease of use and platforms. Kiteworks grades higher on value for money.
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
Kiteworks
Compliance-focused secure file sharing, email and file transfer
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 Kiteworks if
- Fits if you must show auditors how sensitive files leave your company
- Works for teams that need data kept on-premises or in a private cloud
Look elsewhere if
- Not for you if you want to see a price before talking to anyone, as none is published
- Too light for large files on Business, which stops at 2 GB a file against 16 TB on Enterprise
- Skip it if you are a DoD supplier chasing CMMC 2.0 Level 2, where the vendor itself does not recommend Business
- Watch out: bring-your-own-keys, forms and the enterprise integrations are Enterprise only, and Business is 5 to 500 users
How we grade them
| 2.8GPABoxGood | 2.0GPAKiteworksFair | |
|---|---|---|
| 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. | CNo prices are published: Enterprise is call-for-pricing and Business shows only a Buy Now button. Nothing on record to set against the category's $7 middle. |
| 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. | DThe site offers a free trial, but its terms are not stated, so we cannot say it is card-free or longer than a week. There is no free plan. |
| 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. | CIt covers sharing, secure email, SFTP transfer, policy engine and audit log. The listing shows gaps: Business caps files at 2 GB, and bring-your-own-keys and forms are Enterprise only. |
| 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. | CA compliance platform that takes setting up, with policies and integrations to configure. No store rating is on record. |
| 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, with integrations for Outlook, Office, Google Workspace, Salesforce, iManage and Splunk. No desktop or phone apps are listed. |
| Best for | company files with signing and workflows built in | regulated companies sharing sensitive files with outsiders |
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 Kiteworks. How we grade
Where they differ
- Box also covers workflow automation and file sync.
- Kiteworks also covers reports.
At a glance
| Box | Kiteworks | |
|---|---|---|
| Pricing | Free plan | Free trial |
| Starts at | $5 per user / month, billed annually (minimum 3 users) | Not published |
| 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. | None |
| Free trial | Free trial offered on Business Starter, Business, Business Plus, Enterprise and Enterprise Plus | Free trial offered on the vendor's site; terms not stated |
| Web | ||
| macOS | ||
| Windows | ||
| iOS | ||
| Android | ||
| Made by | Box, Inc. | Kiteworks |
| Price read from | peony.ink (not the vendor's own page) | Not confirmed |
| Checked | Oct 5, 2026 | Nov 13, 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.
Kiteworks
- No prices are published: the Enterprise edition is call-for-pricing and the Business edition shows only a Buy Now button.
- Business covers 5 to 500 users with a 2 GB file limit; Enterprise is unlimited with 16 TB files.
- Bring-your-own-keys, forms and the enterprise integrations are Enterprise only.
- Business is not recommended by the vendor for DoD suppliers seeking CMMC 2.0 Level 2.
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.
Kiteworks
- Secure file sharing
- Folders, version control, desktop sync and external collaboration with retention and expiration policies.
- Secure email and forms
- Email protection with DLP scanning, encryption enforcement, link expiration and content withdrawal, plus secure web forms.
- Managed file transfer and SFTP
- Scheduled workflows, an SFTP server for outside parties and air-gapped configurations are described on the site.
- Policy engine and audit log
- One attribute-based policy engine covers every channel, with a single audit log that can feed a SIEM.
- Encryption and compliance claims
- The vendor says it uses TLS 1.3 and AES-256 with FIPS 140-3 validated modules, and states FedRAMP certification.
- MCP server for AI agents
- A Model Context Protocol server lets AI agents reach governed data under the same access rules as employees.
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.
Kiteworks
Pricing could not be confirmed. See kiteworks.com.
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.
Kiteworks
No public discounts listed.
Common questions
Which is cheaper, Box or Kiteworks?
As of Nov 13, 2026, Box starts at $5 per user / month, billed annually (minimum 3 users), and Kiteworks has no price we could confirm.
Which has a free plan, Box or Kiteworks?
As of Nov 13, 2026, only Box has a free plan. Kiteworks does not, though it has a free trial.
Which platforms do Box and Kiteworks run on?
As of Nov 13, 2026, only Box lists macOS, Windows, iOS and Android apps. Both list a web 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.