Dropbox vs iCloud Drive on Mac: pick Dropbox, unless you are all Apple
Pick Dropbox if you want one cloud for ordinary files that works the same on Mac, Windows, Android and the web, with 30 days of version history even on the free plan. Pick iCloud Drive if every device you own is Apple and you want storage built in. Then use only the one you picked.
By Rick van den Broek- Updated
- Prices checked October 2026
- 3 min read
Dropbox
Dropbox for a file system you control. iCloud Drive only if you are all Apple and staying that way.
Pick Dropbox ifOur pick
- You use anything that isn't Apple: a Windows laptop at work, an Android phone, a Linux box.
- You want your files to be plain files, not part of a phone ecosystem.
- You want old versions back, not just deleted files.
Pick iCloud Drive if
- Every device in your life is a Mac, iPhone or iPad, and that won't change.
- You want to share one iCloud+ plan with up to five other family members.
- You don't want to install or sign in to anything else.
| Feature | Dropbox | iCloud Drive |
|---|---|---|
| Free storage | Dropbox2 GB (Basic, up to 3 devices) | iCloud Drive5 GB |
| 2 TB plan | Dropbox€9.99 a month billed yearly, €11.99 monthly (Plus) | iCloud Drive€9.99 a month (iCloud+) |
| Bigger plans | DropboxStandard and Advanced, priced per user | iCloud DriveiCloud+ 6 TB and 12 TB |
| Deleted files and old versions | Dropbox30 days on Basic and Plus | iCloud Drive30 days in Recently Deleted |
| Works on | DropboxMac, Windows, Linux, iPhone, Android, web | iCloud DriveMac, iPhone, iPad, Windows app, web |
| Share a plan with family | DropboxNot on Plus | iCloud DriveAny iCloud+ plan, you plus up to 5 others |
| On your Mac | DropboxAn app and a folder in Finder | iCloud DriveBuilt in, can take over Desktop and Documents |
Most “Dropbox vs iCloud” comparisons end with “it depends”. Here’s the part that doesn’t: whichever you pick, you only get to pick one.
The real question is one cloud, not the best cloud
Two clouds don’t give you twice the safety. They give you two places to look, and one of them is always slightly out of date.
The quiet way this happens on a Mac: Dropbox holds your work, and iCloud Drive holds your Desktop and Documents because macOS offered and you clicked Continue. Now a contract lives in one cloud and its signed copy in the other.
So read this page as “which one becomes the only one”. That’s a decision you make once.
Why the Setup Kit picks Dropbox
Dropbox is independent. It isn’t part of a phone ecosystem, an ad business or an office suite. File storage is the product, so file storage is what gets built.
Your files stay ordinary files. A PDF in Dropbox is a PDF in a folder, on a Mac, a Windows laptop, an Android phone, Linux or the web. If you ever leave, you take a folder with you, not an export project.
It keeps old versions, not just deleted files. Even the free plan keeps 30 days of earlier versions and deleted files, and the business plans keep them longer. Overwrite a spreadsheet by accident on Tuesday and you can still get Monday’s version back.
It has been boring for a long time. Rick has run his whole folder structure on Dropbox since 2013. That’s one person’s experience, not a guarantee, but boring is exactly what you want from the place your tax returns live.
Where iCloud Drive wins
iCloud Drive isn’t a bad choice. For the right person it’s the better one.
- It’s already there. No app to install, no extra account. It’s built into every Mac, iPhone and iPad you sign in to.
- It’s cheaper month to month at 2 TB, as of October 2026: €9.99 a month for iCloud+ against €11.99 for Dropbox Plus billed monthly. Billed yearly, Plus also comes to €9.99 a month.
- One plan covers the family. Any iCloud+ plan can be shared with up to five other people. The free 5 GB can’t.
- The free tier is bigger. 5 GB against Dropbox Basic’s 2 GB, which also caps you at three devices.
If every device in your house is Apple, and you’re sure it will stay that way, iCloud Drive can absolutely be your one cloud.
The setting that quietly gives you two clouds
When you set up a Mac, macOS may offer to keep your Desktop and Documents in iCloud Drive. It’s the most common way people end up with two filing systems without ever choosing one.
Check where you stand:
System Settings[your name]iCloudDriveDesktop & Documents FoldersIf iCloud Drive is your cloud, leave it on. If Dropbox is, this one setting decides whether your Desktop belongs to a second filing system. Moving existing files over safely is its own job, and the Setup Kit has a chapter for it.
Using Dropbox doesn’t mean leaving iCloud
This is the part most comparisons miss. Picking Dropbox for files doesn’t mean switching iCloud off.
| Job | Where it lives with the Setup Kit |
|---|---|
| Working files and documents | Dropbox |
| Photo library | iCloud Photos, or whatever you use today |
| iPhone backups | iCloud |
| Passwords | Apple’s Passwords app |
iCloud keeps doing what it’s good at. It just stops being a second place for files.
The verdict, once more
Pick Dropbox if anything in your life isn’t Apple, or might not be in five years, and you want version history on every plan.
Pick iCloud Drive if you’re all Apple, you want it built in, and you’ll share storage with your family.
Then set it up so the other one can’t quietly collect files. How to organize files on Mac is the next step either way.
One cloud. Pick it on purpose, and the rest of your system has somewhere to stand.
Keep going
See the whole system first
Why one cloud, one folder structure and one naming system make a Mac fast, and what the Setup Kit is and isn't.
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The Setup Kit installs the whole system: 27 chapters, practice tools and the folder wizard with ZIP export.
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