Dropbox vs Send Anywhere (2026): which should you pick?
As of Nov 12, 2026, Dropbox and Send Anywhere share a 2.8 GPA, both have a free plan, and Send Anywhere starts cheaper, at $5.99 a month against $9.99 a month.
Checked Oct 5, 2026 and Nov 12, 2026 · graded Oct 10, 2026 and Nov 12, 2026 by ToolGPA
Dropbox grades higher on features and ease of use. Send Anywhere grades higher on value for money and the free plan. They get the same grade on platforms.
Price, platforms and features side by side. The table says where each price was read and when.
Dropbox
Cloud storage and file sync with transfer and signing tools
Send Anywhere
Send files by 6-digit key or link, with no sign-in on the free plan
Which one is for you
Pick Dropbox if
- Fits if you want 2 TB that syncs across Windows, Mac and Linux
- Works for people who send big files to clients, with transfers of up to 50 GB on Plus
Look elsewhere if
- Tight if you're staying free, because Basic stops at 2 GB
- Pricey if you only need a few hundred GB, as the smallest paid plan is 2 TB at $9.99 a month, the dear end of this category
- Skip it if you want end-to-end encryption for yourself, since it's on Advanced, which needs 3 people
- Watch out: monthly billing costs more, $11.99 for Plus and $18 a user for Standard
- Watch out: there's no trial of Plus, and reviewers say reaching a real person in support is hard
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
| 2.8GPADropboxGood | 2.8GPASend AnywhereGood | |
|---|---|---|
| Value for money | DPlus is $9.99 a month billed yearly, and $9.99 is exactly where the dearest tenth of this category begins, against a middle of $5. You do get 2 TB for it, but there's no smaller paid plan, so a person who wants 200 GB pays for 2 TB or stays on 2 GB. | 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 | CBasic is free for good and it's 2 GB, which one phone's camera roll will fill. There's no free trial of Plus either; the 30-day trial is on the Standard and Advanced team plans only. | BFree: no sign-in, 1:1 live transfers up to 50 GB and links up to 10 GB that expire after 48 hours. |
| Features | BSync across unlimited devices, old versions and deleted files back for 30 days on Plus and a year on Advanced, 50 GB transfers, PDF editing and signing, team folders and an admin console. It misses an A because end-to-end encryption is an Advanced feature needing 3 users. | 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 | A4.8 from about 913,000 App Store ratings, and the thing is a folder: drop a file in, it turns up on your other machines. Reviewers do say reaching a real person in support is hard when something goes wrong. | BNo store rating on record, but there is nothing to set up: pick a file and get a key. |
| Platforms and integrations | AEverywhere: web, Mac, Windows, Linux, iPhone and Android, which is more than most of this category manages. It plugs into Google Workspace, Adobe, Canva and HubSpot, connects to ChatGPT, Claude and Gemini, and has a public API. | AWeb, Windows, Mac, Linux, iPhone, Android and browser extension, with 2 integrations. |
| Best for | one folder that's the same on every computer | 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: Dropbox and Send Anywhere. How we grade
Price against what you get
Dropbox starts at $9.99 a month and scores 3.7 out of 4 on features, ease of use and platforms. Send Anywhere starts at $5.99 a month and scores 3.0.
Dropbox scores higher, and starts $4 a month higher: the question is whether the extra is worth that to you. Of the other file storage and sync services on the chart, none scores higher than Dropbox 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
- Dropbox also covers file sync.
At a glance
| Dropbox | Send Anywhere | |
|---|---|---|
| Pricing | Free plan | Free plan |
| Starts at | $9.99 per month, billed yearly | $5.99 per month, monthly billing |
| Free plan | Basic plan: 2 GB to store and share files. | Free: 1:1 real-time transfers up to 50 GB and links up to 10 GB; links expire after 48 hours. |
| Free trial | 30-day free trial on the Standard and Advanced team plans | None listed |
| Web | ||
| macOS | ||
| Windows | ||
| Linux | ||
| iOS | ||
| Android | ||
| Browser extension | ||
| Made by | Dropbox | Rakuten Symphony Korea, Inc. |
| Price read from | dropbox.com | send-anywhere.com |
| Checked | Oct 5, 2026 | Nov 12, 2026 |
Worth knowing
Dropbox
- The free Basic plan includes only 2 GB of storage.
- The cheapest paid plan is Plus at 2 TB for one person; the plans page lists no smaller paid tier.
- End-to-end encryption, single sign-on and audit logs are limited to Advanced, which requires at least 3 users.
- Monthly billing costs more: $11.99 for Plus and $18 per user for Standard, against $9.99 and $15 on yearly billing.
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
Dropbox
- Sync across devices
- Files stay in sync between the desktop apps, the mobile apps and the web, and every paid plan allows an unlimited number of connected devices.
- File recovery and version history
- Deleted files and earlier versions can be restored for 30 days on Plus, 180 days on Standard and 1 year on Advanced.
- Large file transfers
- Send a copy of files by link: up to 50 GB per transfer on Plus and up to 100 GB on Standard and Advanced, where transfers can also be password protected.
- PDF editing and signatures
- Edit, annotate and sign PDFs inside Dropbox. The paid plans list unlimited self-signing and 3 signature requests per month.
- Team folders and admin console
- Standard adds team-owned folders, groups and an admin console. Advanced adds tiered admin roles, audit logs with file event tracking and single sign-on.
- Connections to AI tools
- Dropbox content can be connected to AI tools such as ChatGPT, Claude and Gemini to find and summarize files and save work back to Dropbox.
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
Dropbox
Basic$0
2 GB to store and share files.
Plus$9.99
per month, billed yearly ($11.99 billed monthly)
For 1 person: 2 TB of storage, 30 days to restore deleted files and transfers of up to 50 GB.
Standard$15
per user / month, billed yearly ($18 billed monthly)
For 1 person or more: storage starts at 3 TB for the team, 180-day restore, 100 GB transfers, team folders and admin controls.
Advanced$24
per user / month, billed yearly ($30 billed monthly)
For 3 people or more: storage starts at 15 TB, 1-year restore, end-to-end encryption, single sign-on and tiered admin roles.
EnterpriseCustom
Custom pricing with integrations for third-party security tools and live support from dedicated staff.
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
Dropbox
- Annual discount
About 17% to 20% lower with yearly billing
Billed yearly, Plus is $9.99 a month instead of $11.99, Standard is $15 per user instead of $18, and Advanced is $24 per user instead of $30.
Send Anywhere
No public discounts listed.
Common questions
Which is cheaper, Dropbox or Send Anywhere?
As of Nov 12, 2026, Send Anywhere is cheaper to start with: $5.99 a month, against $9.99 a month for Dropbox. Dropbox starts at $9.99 per month, billed yearly, and Send Anywhere starts at $5.99 per month, monthly billing.
Which has a free plan, Dropbox or Send Anywhere?
As of Nov 12, 2026, both Dropbox and Send Anywhere have a free plan.
Which platforms do Dropbox and Send Anywhere run on?
As of Nov 12, 2026, only Send Anywhere lists a browser extension. Both list a web app and macOS, Windows, Linux, iOS and Android apps. 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.