MacOS causing incompatibility issues with dropbox and google drive

I avoid iCloud for good reasons and back up my files with Dropbox instead. That is not an excuse for Apple or Dropbox to break basic backup functionality.


On macOS with the new File Provider framework, I discovered a serious problem. I’m on Dropbox Plus, with the desktop app installed on the latest macOS. I don’t use Smart Sync — all my files are set to be fully local. During a manual copy/paste backup to an external drive, I found that copying my Dropbox and Google Drive folders only created alias folders instead of real data, even though Finder marked them with green checkmarks as offline. This means a backup could look correct while being completely useless.


The worst part: once copied onto the external drive, Finder reports these alias folders as having the same size as the originals, so you think the data is there. Only Disk Utility revealed the discrepancy (the backup size did not match expectations). From a user’s perspective this is broken: if I copy a local folder to another drive, it should always copy the real contents, not a managed alias. I understand those folders are actually treated like aliases, so technically this is right, but it was not my decision to do so, when those cloud services were installed. If a power user like me can easily fail to notice this, imagine a non-savvy user.


To make it worse, Time Machine backups don’t include Dropbox data at all under File Provider. If all my files live in Dropbox, Time Machine becomes essentially useless as a safety net. A backup solution that ignores a user’s main file storage is not a backup system. This means I can rely on Time Machine only for a backup of my macOS configuration, including OS-wise settings and installed app, and that's it. This is a shame because the incremental backup feature would be very useful, and add an extra layer of security on top of Dropbox.


Dropbox and Apple need to fix this. If the user copies an alias folder, the system should prompt to copy the real contents. Otherwise, the File Provider migration creates a huge risk of accidental data loss. Don’t mess with user data. Also, don't make macOS a walled garden, where things are only going to work if you use Apple software. I value the fact that I can choose, and don't have to stick with software and solutions provided by Apple, which are, in the vast majority of cases, mediocre at most.

Mac mini (M4)

Posted on Jul 30, 2025 7:57 AM

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11 replies

Aug 5, 2025 12:02 PM in response to steve626

Thank you for the help Steve, much appreciated. I did get in touch with Dropbox and they say that most likely, the problem is that the installation of Dropbox on my machine is running without a system extension that enables to switch between online only and available offline (see screenshot from Matti). I had to check it in the settings on my Dropbox.com account, and now I have to uninstall and reinstall Dropbox, for this option to work as expected. Glad things are working fine on your side.

Jul 31, 2025 7:17 PM in response to lucben

lucben wrote:

I avoid iCloud for good reasons and back up my files with Dropbox instead. That is not an excuse for Apple or Dropbox to break basic backup functionality.

I’m on Dropbox Plus, with the desktop app installed on the latest macOS. I don’t use Smart Sync — all my files are set to be fully local. During a manual copy/paste backup to an external drive, I found that copying my Dropbox and Google Drive folders only created alias folders instead of real data, even though Finder marked them with green checkmarks as offline. This means a backup could look correct while being completely useless.

I use Dropbox and configure it so all files are stored locally AND in the Dropbox cloud storage online.


I have two kinds of backups: (1) Time Machine; and (2) SuperDuper, a clone type backup.


Both make complete and valid physical copies of all my Dropbox files. I just did a test restore of some Dropbox files from a Time Machine backup. I can see those files inside the Time Machine backup sets on the Time Machine drive, and can restore them either via the Time Machine interface, or by simply drag/drop.


SuperDuper also copies all the Dropbox files into its external backup drive. I have tested this carefully.


I can also manually copy the Dropbox files. I get true copies, not aliases.


So I cannot reproduce your problem. I also don't see any evidence of it in Dropbox forums.

To make it worse, Time Machine backups don’t include Dropbox data at all under File Provider. If all my files live in Dropbox, Time Machine becomes essentially useless as a safety net. A backup solution that ignores a user’s main file storage is not a backup system. This means I can rely on Time Machine only for a backup of my macOS configuration, including OS-wise settings and installed app, and that's it. This is a shame because the incremental backup feature would be very useful, and add an extra layer of security on top of Dropbox.

This is not correct. My Time Machine backups have all my Dropbox files.


You should investigate your Dropbox installation and configuration. Maybe with help from Dropbox support. What you are describing sounds a lot like the files are not physically stored on your local drive but are only in the cloud. For that setup, I believe that neither Time Machine nor clone type backup utilities will make true backups.

Aug 5, 2025 8:03 PM in response to lucben

lucben wrote:

Quite possibly, my Dropbox was installed prior to the switch to File Provider, not sure. This is a nightmare because it looks like if you need to update Dropbox, you have to uninstall it, then install it again, and wait 2 days for all contents to be downloaded again locally, because Dropbox doesn't have a system to match files stored locally with those stored online.

Everyone who was using Dropbox when they switched over to File Provider had it installed prior. From what I have read in the Dropbox forums, the vast majority of problems occurred when people had their Dropbox folder stored somewhere other than the boot drive, which doesn't work.


But glitches can happen, and it does sound like a damaged installation. So I would uninstall Dropbox completely and then reinstall it. I would not try to "trick" it by doing something odd that might speed up the downloads, I would let it proceed normally. I don't think one has to wait 2 days for the download; how much do you have in Dropbox? Even if you have 1 TB there, even at 100 Mbps that's 40 GB per hour, or about 1 TB in about 1 day. I actually get 450 Mbps download speed so for me it would be about 5 hours. But even if it does take you two days, just wait and it will complete. The good thing about Dropbox is that it picks up where it left off when it is interrupted. You originally posted about a week ago so it would have long been downloaded by now ...

Jul 30, 2025 8:28 AM in response to lucben

apple will not read your plea here


these forums are user helping other users like yourself, it's sort of going

to a physical apple store and asking other customers there advice


try reaching out to them using


Get Support (apple.com)

And or

Contact - Official Apple Support

And or

Contact - How to Contact Us - Apple

Or

Genius Bar Reservation and Apple Support Options - Apple



or dropbox

Dropbox - Contact Dropbox support

Aug 5, 2025 12:07 PM in response to Matti Haveri

Hi Matti, yes that location of my Dropbox is correct and I am not using an external drive, all is on my internal drive. Something must be wrong with my installation (see answer to Steve). Quite possibly, my Dropbox was installed prior to the switch to File Provider, not sure. This is a nightmare because it looks like if you need to update Dropbox, you have to uninstall it, then install it again, and wait 2 days for all contents to be downloaded again locally, because Dropbox doesn't have a system to match files stored locally with those stored online. I bet this would not be so much of a technical challenge, one could mark them with unique tokens, but who knows, I haven't looked into the technical details. Thank you anyway, I appreciate your help.

Aug 5, 2025 12:36 PM in response to lucben

> wait 2 days for all contents to be downloaded again locally


I have sometimes just by brute force copy-pasted an existing local copy of Dropbox contents to a new Dropbox install’s folder. Then Dropbox does not have to download them and it takes only a little time for it to figure out how to sync that to what is online.


…but when troubleshooting your issue I’d not use that hack.

Aug 5, 2025 3:18 PM in response to Matti Haveri

I have sometimes just by brute force copy-pasted an existing local copy of Dropbox contents to a new Dropbox install’s folder. Then Dropbox does not have to download them and it takes only a little time for it to figure out how to sync that to what is online.


That would be an amazing hack, but did you test it? How do you know that Dropbox is not going to get confused? And how does it know, in case it does detect al conflicts, whether the source of truth is the offline version, or the online version? Considering that a re-installation is going to interrupt sync, this is not a trivial issue

Aug 5, 2025 4:32 PM in response to lucben

lucben wrote:

I avoid iCloud for good reasons and back up my files with Dropbox instead. That is not an excuse for Apple or Dropbox to break basic backup functionality.


?


Never had an issue with iCloud and/or Dropbox— which works like it always has for me on macOS 15.6



if in doubt about your third party apps—if in doubt search the developers website or contact their: Support/Help/FAQ/Known issues/compatibility/updates…


Contact a third-party vendor - Apple Support

Contact a third-party vendor - Apple Support




Verify your software is up to date…

The current stable release of Sequoia including bug fixes, security updates is macOS 15.6

Keep your Mac up to date - Apple Support

Keep your Mac up to date - Apple Support












Aug 5, 2025 8:36 PM in response to lucben

> And how does it know, in case it does detect al conflicts


I have copy pasted the very recent copy of the online version so there are no conflicts. But as I said, I’d not use that method when troubleshooting. And besides, I don’t have any mission critical in Dropbox so I am more free to mess around with its contents…


One option to speed up the initial sync is to have another Dropbox Mac in the same local network — AFAIR Dropbox has a setting to then sync via the local home network which is usually faster than the network outside.

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MacOS causing incompatibility issues with dropbox and google drive

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