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Some files are stuck on"waiting to upload" and never sync on macOS unless I double click them.

When adding files to my Dropbox folder on my Mac, I occasionally see some files which appear in the Finder with a dotted line cloud icon in the state "waiting to upload". These files will never sync to Dropbox or my other computers until I manually double click on the file to open it, and THEN the sync starts and shows up on my other computers running the Dropbox app.

In case it matters, these files are being created automatically in the Dropbox folder by my scanner software (ScanSnap). This does not happen with all files created by ScanSnap, it seems to happen occasionally to random files (90% of files seem to sync correctly).

I'm seeing this on macOS Sequoia 15.1.1 with Dropbox v212.4.5767

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Comments

Megan

Hey @cdwilson, let's jump right into this!

First of all, thanks for sharing the device's OS and Dropbox version, along with screenshots.

Do you recall approximately when this started happening? If you temporarily quit ScanSnap, do you notice the same behavior?

Let me know more, and we'll take it from there!

cdwilson

Hi Megan,

I only just signed up for the Dropbox Family plan a couple weeks ago, and I've noticed this behavior over the last week or two (maybe since I signed up, can't remember exactly when I first started seeing it). I can't reproduce this behavior if I create files in the folder manually (with or without the ScanSnap software running).

They way I have things set up now: I have a (headless) mac mini with the scanner attached via USB, and the ScanSnap software is set to scan the document into a file in my dropbox when I push the button on the scanner. Usually the file is created, added to the Dropbox folder, and is sync'd so that it's available on my other computers running Dropbox. But occasionally, one of the files created by ScanSnap ends up in the "waiting to upload" state, and then it never syncs to Dropbox until I log into the mac mini (via Remote Desktop) and double click on the file. After manually poking the file it successfully syncs and I can access it on my other Macs. It appears random to me which files end up having this issue (I use the same process and for most files everything works fine).

Thanks for the quick reply!

Megan

Hey @cdwilson, thanks for all the details!
Based on what you described, it sounds like it has to do with ScanSnap and the app's settings upon creating the files in your Dropbox folder.
Have you tried contacting them by any chance?
However, give me some time to check internally with our Team about this, and I'll let you know more.

cdwilson

Hi @Megan

As far as I can tell, ScanSnap is just creating normal files under the Dropbox "Family Room" directory.

The only difference I can see between files created by ScanSnap vs. file created manually by myself is the permissions group is set to "wheel" for files created by ScanSnap, while the group is set to "staff" for files I create manually.

On the mac mini, the logged in user is a "Standard" user (not an Administrator). As far as I know, this all shouldn't make any difference, but I figured I'd mention it in case it matters.

Since the whole process works most of the time, I'm wondering if maybe there is some kind of timing/race condition issue that is happening due to the fact that the files are being created (and possibly renamed) quickly by a program, rather than manually by a human.

Is there any kind of logging or debug I can enable in the Dropbox app that might help to see why this is happening?

cdwilson

Hi @Megan

In case you want to share with your internal team, here's the sequence of file system events when ScanSnap saves a scanned PDF document in the Dropbox folder:

<redacted>@<redacted> Downloads % ./fswatch -x /Users/<redacted>/Library/CloudStorage/Dropbox/Family\ Room/Scans
/Users/<redacted>/Library/CloudStorage/Dropbox/Family Room/Scans/CheckFolderValid0000000000 Created IsFile Removed
/Users/<redacted>/Library/CloudStorage/Dropbox/Family Room/Scans/1E50072C-065E-45B4-BD1A-C383B63EFD39/A Created IsDir Removed
/Users/<redacted>/Library/CloudStorage/Dropbox/Family Room/Scans/1E50072C-065E-45B4-BD1A-C383B63EFD39 Created IsDir Removed
/Users/<redacted>/Library/CloudStorage/Dropbox/Family Room/Scans/2024-12-04-16-11-18.pdf Created IsFile Link
/Users/<redacted>/Library/CloudStorage/Dropbox/Family Room/Scans/2024-12-04-16-11-18.pdf AttributeModified IsFile Link
/Users/<redacted>/Library/CloudStorage/Dropbox/Family Room/Scans/2024-12-04-16-11-18.pdf AttributeModified IsFile AttributeModified Link
/Users/<redacted>/Library/CloudStorage/Dropbox/Family Room/Scans/2024-12-04-16-11-18.pdf AttributeModified IsFile AttributeModified Link

Megan

Hey @cdwilson, if you quit/relaunch the app without clicking on the files first, do they still appear as "waiting to sync"?

Also, have you noticed this behavior specifically for files in the Dropbox Family Room, or does it happen regardless of the folder destination?