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Migrated to new MacBook Air results in 11 unsynced files and slow MS Word.

A few weeks ago I migrated from an old Intel MacBook Air (machine no longer available) to an M3 MacBook Air using Migration Assistant. I am currently running Sonoma 14.5 and Dropbox 203.4.4857. I am "eligible" for Dropbox for macOS on File Provider but have not gone through that process.

Issues:

1) The Dropbox menu item reports 11 files have not been synced and will take 45 minutes, but they never sync. When I look at them in the Finder, I see the blue sync circle next to the file name. Thousands of other files have appeared to sync properly with the checkmark icon. I believe most these are documents shared with other Dropbox users who have edit rights. Other shared documents seem to sync properly, just these 11.

2) When working with a Microsoft Word document from the Dropbox folder that DOES appear to be syncing properly (checkmark icon NOT blue sync circle), Microsoft Word will eventually slow to a crawl with spinning beach ball.

I have rebooted multiple times, which temporarily fixes the Word slowdown.

I have downloaded and reinstalled the latest Dropbox app several times without uninstalling Dropbox.

I have tried renaming the unsynced files to simple names with no punctuation.

Per a previous thread suggestion here, I looked for duplicate Dropbox apps in ~/Library/Application Support/Dropbox and did not find any. The only Dropbox app appears to be in the Applications folder. However, I DID find "~/Library/Application Support/Dropbox Electron" (created 5/12/22 604KB) in addition to "~/Library/Application Support/Dropbox" (Created 3/9/2017 with 3.3MB). Am I supposed to have both these folders?

My next step, would be to completely delete Dropbox from the new Mac (app, files/folders in library, synced files, etc), reinstall Dropbox and let it bring down all the files from the Dropbox server. That is about 250GB, so I'd rather not if there was a better solution.

Any suggestions to resolve the above issues?

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Megan

Hey @markelp, wishing you a happy Monday!

Let me apologize for the length of my post, I just want to make sure we've covered everything here.

What is the file type of these 11 files that the app has a hard time syncing? Also, when did this first start happening? Was it when you first downloaded the app on the new device?

Now, onto the Word issue. If you temporarily quit the app, and then try to open an example Word file from within the Dropbox folder what happens then?

One more thing I'd like for us to check is how many files you have inside your Dropbox folder at the moment? You can locate your Dropbox folder within Finder, and right click on it before selecting "Get info". If you have a screenshot, feel free to attach it here.

Keep me posted, and we'll take it from there!

markelp

Thank you for the prompt reply. My responses inline below:

What is the file type of these 11 files that the app has a hard time syncing? Also, when did this first start happening? Was it when you first downloaded the app on the new device?

--- They are a variety of files, mostly .DOCX, .PPTX and .XLSX. I also just noticed that there are 3 or 4 folders with the blue sync icon, but there appears to be no files under those folders with the blue sync icon (all files in those folders have the checkmark icon).

Now, onto the Word issue. If you temporarily quit the app, and then try to open an example Word file from within the Dropbox folder what happens then?
--- Please clarify "from within the Dropbox folder". Do you mean double-clicking the icon in the Finder within the Dropbox folder? Or using the "Open" command in Word. I have tried both with the same results, but will test which ever you would like.

One more thing I'd like for us to check is how many files you have inside your Dropbox folder at the moment? You can locate your Dropbox folder within Finder, and right click on it before selecting "Get info". If you have a screenshot, feel free to attach it here.

--- 49,627 items with 256GB on disk. See attached. This is a small portion of the 2TB subscription allocation.
--- I also included a screenshot of the message I see at the bottom of the Dropbox menubar icon showing the 11 items that never sync. Not sure if that helps.

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Megan

Hey @markelp, awesome, great job on the details!

Now as for the syncing files, let's try to sign out of the app and then back in to see if this changes things at all.

Also do you have any proxy, VPN, firewall, security software, or even ISP/router settings that could be restricting traffic to the following Dropbox domains?

The files that you have stored locally inside the Dropbox folder don't exceed the 300K soft limit that our app has, so that seems to be okay.

As for Word: you can quit the Dropbox app, and then locate your Dropbox folder inside your Finder and open your files by double clicking on them.

markelp

Signing out/in resolved most of the sync issues after about an hour. But the menu bar icon drop down reported were still three files not completed. When I looked through the Dropbox folder, there was one file and two folders with the blue sync icon (but no unsynced individual files in those folders). It appears the Excel file has some permissions issues as it has a lock on the icon. I will let it run overnight and see if anything else changes.

The firewall is not enabled on the Mac. I will check the router settings and VPN today. Along with the recommendation to quit Dropbox then open a local copy of the file in Word to see if there are changes.

Can you confirm if "~/Library/Application Support/Dropbox Electron" (created 5/12/22 604KB) and "~/Library/Application Support/Dropbox" (Created 3/9/2017 with 3.3MB) should be on my system?

Megan

Hey @markelp!

These entries are most likely from an older installation of Dropbox.

There's a chance that they might be outdated, but I wouldn't necessarily recommend that you remove them from your system, especially since they don't take up so much space.

markelp

Thank you, Megan. Please see below:

1) "Now as for the syncing files, let's try to sign out of the app and then back in to see if this changes things at all."

- After signing out and back in and letting the Dropbox app/services run for several day, it still reports three files not syncing. Looking at the Dropbox folder, there is one .xlsx file that still have the blue sync icon and two folders. Any additional recommendations to resolve these errors?

- Additionally, after this process I notice that Dropbox is asking for the macOS Admin password at each launch/reboot with the message: "Dropbox needs to change permissions for the Folder: /Users/xxxxx/Dropbox". Is this normal?

2) "As for Word: you can quit the Dropbox app, and then locate your Dropbox folder inside your Finder and open your files by double clicking on them."

- This seems to have solved the problem with Word slowing down when using a local .docx file that is synced with Dropbox. However, quitting and relaunching Dropbox each time I want to edit a Word document is frustrating. Is there a root cause/permanent solution that would allow me to edit in Word while Dropbox is still running?

3) "Also do you have any proxy, VPN, firewall, security software, or even ISP/router settings that could be restricting traffic to the following Dropbox domains?"

- As mentioned above, there is no firewall configured on this Mac. I do not see ISP/router settings that could be blocking Dropbox. In fact, other computers on this ISP/router/network use Dropbox without problems.

- This machine does have "GlobalProtect 5.2.7-37" installed for some specific workflows with a company. However, it is not enabled when the above Dropbox issues appear. If you have some additional troubleshooting steps to determine if it is conflicting with Dropbox, it would be appreciated.

- Regarding the Dropbox domains list you provided above, a spot check via a browser shows that some resolve to a Dropbox site but others do not. This is consistent on multiple machines. I also attempted a ping a few in terminal:

PING dropbox.com (162.125.248.18): 56 data bytes

64 bytes from 162.125.248.18: icmp_seq=0 ttl=54 time=5.898 ms

PING s3-us-west-1-w.amazonaws.com (52.219.220.121): 56 data bytes

64 bytes from 52.219.220.121: icmp_seq=0 ttl=242 time=79.131 ms

ping: cannot resolve dropboxexperiment.com: Unknown host

ping: cannot resolve addtodropbox.com: Unknown host

ping: cannot resolve dropboxapi.com: Unknown host

If the above is not as expected, can you provide additional advice/methods to test if my system/network/router is "restricting traffic"?

Depending on the answer to #1 and #2 above, I am still leaning towards completely deleting Dropbox from this Mac (including all synced files/folders and supporting files in ~/Library). Then reinstall and let it sync from the Dropbox servers. Is there a KB article to walk me through this process to ensure I delete everything related to Dropbox and successfully reinstall/resync?

Thank you.

Megan

Hey @markelp!

Would you mind clarifying your app's current syncing status, please? If you could send me a screenshot of that, I'd definitely appreciate the visual.

You also mentioned that the app asks for your password each time. Have you made sure that the app has been installed with admin rights?

As for the little test we tried with Word, I'm assuming you didn't have any issues while Dropbox wasn't running right? In this case, we might need to have a closer look into this to see what might be causing it. Does this happen with all of your Word documents?

Lastly, I could guide you as to how you can uninstall Dropbox from your device. Once the process is done, you can go ahead and delete your local Dropbox folder. Once that's done you will simply go ahead and re-install the app and allow for your content to sync to your device.

markelp

1) Would you mind clarifying your app's current syncing status, please? If you could send me a screenshot of that, I'd definitely appreciate the visual.

I have attached screenshots of the drop down from the menubar icon showing "Syncing 3 files" (which has remained this way since I logged out and back in per the instructions above - it used to be "Syncing 11 files") and the Sync Issues screen showing "No issues".

2) You also mentioned that the app asks for your password each time. Have you made sure that the app has been installed with admin rights?

I installed it as I do all apps without anything special/different. I entered the admin password as requested during install and subsequent requests. There is only one user on the Mac. I assume it is installed with Admin privileges.

I have attached the screenshot of the dialog that is presented each time the Dropbox app is launched after reboot or quit. Note, this also triggers a re-sync of all files which takes about 15 minutes to scan through the 49,000 files and ends with the "Syncing 3 files" mentioned above.

3) As for the little test we tried with Word, I'm assuming you didn't have any issues while Dropbox wasn't running right? In this case, we might need to have a closer look into this to see what might be causing it. Does this happen with all of your Word documents?

It happens when editing a Word document that is also synced with Dropbox. It the slowdown seems to occur more often when "Track Changes" is on in Word, but I haven't tested it extensively. The issue does NOT occur when I quit the Dropbox app prior to opening the Word document.

4) Lastly, I could guide you as to how you can uninstall Dropbox from your device. Once the process is done, you can go ahead and delete your local Dropbox folder. Once that's done you will simply go ahead and re-install the app and allow for your content to sync to your device.

I have not done this yet. I'd rather understand and resolve the issues in #1-3 above before I attempt a delete/reinstall.

Thank you.

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