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Repeatedly requests to change permissions, not syncing in user folder located on second drive

A couple of weeks ago I upgraded my mid-2010 MacPro 5,1 to Mojave (installing a new video card along the way), and decided to move my user folder (including my 400GB Dropbox folder) off my SSD (where the OS resides) onto a different hard drive, following the procedure to target the app towards the new location. Although it seemed to work at the outset, I have since been hit with a window saying "Dropbox needs to change permissions" whenever Dropbox starts, and entering my system password does not stop it from asking again next time. Meanwhile the app is not syncing properly. Here's the step-by-step of my ground-up procedure:

After referencing this forum discussion (though this user apparently had no problems syncing, just indicator visibility), I took the precaution of removing the only other 3rd-party extension visible in Preferences>Extensions>All, as well as disabling the four Quick Actions visible in Preferences>Extensions>Finder.
Unlinked account
Uninstalled Dropbox app and restarted computer. Noted that the Dropbox folder's icon still bore the brand logo.
Reinstalled Dropbox app
Ensured the app was pointing at the correct location of my Dropbox folder
Ensured my user profile had read/write permissions on user folder and Dropbox folder
Noted that all my Dropbox content was wearing blue sync flags; app was busy "checking for changes". I gave it a 45-minute breather, but it didn't change state. I restarted the computer and was asked for permission to change permissions again.

Followed procedure at Dropbox Help for resolving permission errors, replacing original ~/Dropbox arguments with my new User folder path as follows:

sudo chflags -R nouchg /Volumes/Wasteland/Moved\ OSX\ Users/myUser/Dropbox ~/.dropbox ~/.dropbox-master

- Responded with ".../.dropbox-master: No such file or directory"

sudo chown "$USER" "$HOME"

sudo chmod -RN ~/.dropbox /Volumes/Wasteland/Moved\ OSX\ Users/myUser/Dropbox

chmod -R u+rw /Volumes/Wasteland/Moved\ OSX\ Users/myUser/Dropbox ~/.dropbox

Restarted Dropbox app; was asked for permission to change permissions again. Entered my password.
Noted that my app window now says "Syncing 5,193 files". Decided to disregard this for a moment to play it safe and reboot off of a USB installer to do quick First Aid scans on my OS and User drives to make sure there weren't any permission errors.
After rebooting normally noted that Dropbox was again "syncing 5,193 files" and that, after about 20 minutes, I had not yet been presented with another window begging permission to change permissions, I decided for funsies to alt-Account in the Dropbox preferences and "fix permissions". It asked for my system credentials, which I provided. It then returned a "success" message.
Closed and restarted Dropbox app to test if I would be once again asked permission to change permissions on loading. I was. I sighed heavily and provided my password. Dropbox began "checking for changes". After an hour, there has been no update to this status.

Cheering myself up at the knowledge that a 400GB block may take a bit of time to index, I'm going to leave the machine to its own devices for the night, in the hopes that maybe something cracks loose. But, since I doubt anything's really been fixed, I'm going to post this help request. Thanks for reading!

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xyzzy

So the problem apparently turned out to be "symbolic links" (symlinks) hidden in a few minor apps I had floating in Dropbox. Lusil's reccommended actions were as follows:

"Symbolic links, Junction Points, or "symlinks", occur when folders are added to Dropbox that reference directories outside of the Dropbox folder or inside of the Dropbox folder but in a different folder. Because these symlinks may reference locations where Dropbox may have limited accessibility, they can cause various issues, such as high CPU usage, poor syncing performance, and permissions issues.

The problem you described may be related to such symlinks in your Dropbox folder, so could you please run the following command to determine if there are any in your account?

1) Open your Terminal app (Located at /Applications/Utilities/Terminal). You can also search for "Terminal" using the magnifying glass at the top of your screen
2) Copy and paste the following line into the Terminal: find ~/Dropbox -type l -exec ls -lah {} \;

This should give you a list of symlinks in your Dropbox folder and shows you the full file path to every symlink in your account.

If you do find symlinks in your account, we recommend that you remove them. You can do that by following the file paths that are provided when you run the command, and remove the files in your Dropbox folder by dragging them elsewhere on your computer (if you don't want them deleted).

After you've removed all of the symlinks you can identify from the Terminal command, please quit Terminal, open it again, and run the command again to ensure that no symlinks remain in your Dropbox folder.

If the symlink pathway is part of a single file that is visible in your Dropbox folder on your computer, this symlink may be part of a container file. Container files look like regular files if you look at them on your computer, but they're actually wrappers that contain other file types inside of them. These may include files necessary for the application to run properly and load all the components that the file requires, with some examples of these types of files being iPhoto libraries, Aperture files or iWork files.

In these cases, you may want to remove the entire container file, rather than just the symlink itself, as removing just a component of the container file could damage the container file and therefore you may have problems when opening it.

In general, we recommend users move the actual folders into the Dropbox folder and then symlink back to the original locations. Please just keep in mind that we don't generally support the use of symlinks due to the issues that can arise when they are added to Dropbox.

After you remove the symlinks, it can take some time for syncing to get back to normal. I recommend restarting your computer and then checking on the status of Dropbox. Please give the application some time to re-index and begin the sync process again."

...And, it worked. I am now syncing successfully. The Terminal command revealed a number of these symlinks embedded in a few minor apps (a couple of retro games and some console emulators), which I was more than happy to move outside of Dropbox. After a computer restart, Dropbox began syncing normally. Thanks so much for your help, Lusil!

All comments

Lusil

Hey @xyzzy, awesome work on the troubleshooting!

One more step that you could try would be an advanced reinstall, it might just do the trick.

If you’re still having trouble with this though, let me know and I’d be more than happy to further investigate this with you via email due to account specific info that’ll be required.

Let me know how it goes!

xyzzy

Ah, Advanced Reinstall? Going for the deep cuts now. I followed the steps as documented, properly adjusting my User folder path. I noted that at no time did the Dropbox folder lose its special icon, and saw that when the new installation was in, it already had my proper User folder targeted; I don't know if that's relevant, but thought it worth mentioning. I also restarted the computer at the end of the process, and see Dropbox is now "checking for changes". (It also asked for permission to change permissions again.) I'll see what progress has been made when I get back from work and update the thread. Thank you for your help!

Lusil

No worries, @xyzzy , take your time!

xyzzy

Regrettably, Dropbox is still "checking for changes" after a good ten hours.

xyzzy

Hmm, after a little while it asked for permission to change permissions. I entered my password, then noticed that Dropbox is now "syncing 2,093 files", so I have that going for me, which is nice. We'll see if it makes any more progress.

Lusil

Syncing your files can take time if you have many files or large files, but please note that the time left that it reports is an "instant" estimate based on the current upload speed. This value can change if you check the value just a few seconds later.

If the sync time is large then you need to remember to stay logged into your computer and to keep that computer turned on and connected to the Internet. Dropbox syncs your files in the background.

Spoiler

Finally, I also wanted to mention that that Dropbox can only upload/download as fast as your ISP allows. Although, normally, Dropbox doesn't use all of your bandwidth, you can change that by manually setting the upload/download speed. But please bear in mind that setting your Upload to Don't Limit or higher than what your connection is capable of will likely cause all other Internet activity on your network to slow significantly.

Having said that, please give it some time, and if it doesn’t go down or the initial behavior reappears, just give me a shout and I’ll get back to you as soon as possible.

Thanks in advance, @xyzzy !

xyzzy

Nothing developed; I think I'm back to square one.

Lusil

Sorry to hear that, @xyzzy .

In order to have a more in-depth look into this and due to account-specific info that’ll be required, I’ve sent you an email to the email address associated with your Forum profile. Please check your inbox for my latest message and we’ll take it from there.

Looking forward to hearing back from you!

xyzzy

So the problem apparently turned out to be "symbolic links" (symlinks) hidden in a few minor apps I had floating in Dropbox. Lusil's reccommended actions were as follows: