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Setting folders to Online-Only has left countless orphaned files on Mac OS

I have a folder in Dropbox called "~ ~ 0 DropBox Only." For ease of reference, I'm just going to call it "Dropbox Only." It contains many many folders that I intended to make online-only, having started with all Dropbox folders being synced normally. I had assumed that the local hard-drive based files would disappear.

What I did not realize is that the folder structures and file names were not removed. It took me quite some time to realize this.

As a result, I saved a number of files into folders in the Dropbox Only folder.

In Finder, what I see is that files in the Dropbox Only folder (which could be several layers down in the folder structure) have either a cloud with a down arrow, a cloud with an exclamation point, or just a cloud.

If a file in Dropbox Only is "orphaned," has a cloud with down arrow, and I try to open it, I get "Couldn't communicate with a helper application. Try your operation again. If that fails, quit and relaunch the application and try again." If it has a cloud with an exclamation, then I get "The document "xxxx" could not be opened. Try your operation again. If that fails, quit and relaunch the application and try again."

If I try to open the "orphaned" file from within an application, the application often hangs or has other issues.

Files and Folders added since the shift to online only-behave normally.

I likely have thousands of "orphaned" files. I would happily just delete the folders, but at this point, I have many important files that have been added to some of these folders which I cannot afford to lose.

If I could visually identify the "orphaned" files by their cloud status, that would help, but an "orphaned" file and a regular file that is not currently synced both show a cloud with a downward arrow.

I'm tempted to change the status of the Dropbox Only folder to normal syncing, but (1) I don't know what will happen to files added since the syncing change and (2) I doubt I have enough disk space to hold the full contents of Dropbox Only.

I am just looking for general guidance that allows me to either remove large numbers of "orphaned" files or restore them to normal syncing.

Also, if I do successfully restore a sub-folder to normal syncing and then want to move it back to online-only, do I need to go through and delete all the affected file and folder entries on my hard drive? Presumably, the hard-drive versions are all "orphaned" at this point?

With certain critical folders, I have renamed folder xxxx to xxxx_B on the hard drive. I then download the Dropbox version of xxxx. I find that xxxx and xxxx-B do not have all the same file and sub-folder names, so I have to painfully go through and check them against each other. This solution will not scale up to cover the thousands of files and folders. For now, I just use the xxxx folder, and if I am missing something, I look for it in the xxxx_B folder and move it to the xxxx folder.

This is all a horrible mess, and I am just trying to find a way forward. Any help or thoughts are appreciated.

macOS Sequoia 15.3.2

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Comments

Jay

Hi @xmarc999, thanks for bringing this to our attention.

It sounds like you were looking for something similar to selective sync, which would prevent the entire folder and all files within from appearing on your local machine.

Could you clarify what you mean by orphaned files exactly?

A screenshot showing this would be appreciated.

xmarc999

In looking to make good screenshots, I found that the problem is scattered across various folders within Dropbox. All of the folders impacted have been turned on and off for selective syncing over time.

By "orphaned," I mean that everything about the folders and files look normal when viewed using Finder on the Mac. But when I try to open them, either directly from Finder or from the "Open" dialog within an application, I get some sort of error, or nothing happens.

In this first composite screenshot, I try to open a PDF and get the error shown:

In the first frame, we see two files in a folder. The first has a cloud icon with an exclamation, and the second has a cloud with a downward arrow. Both get the same error when I try to open them.

xmarc999

Second example and the more common occurrence:

Here we see a pdf (p502 copy.pdf) in a folder. From the Finder window, all looks normal, although the cloud icon has an exclamation. The second frame shows the error "Couldn't communicate with a helper application." On an "orphan" file, I get this error regardless of what the cloud icon shows.

In all cases, if I log into Dropbox and navigate to the corresponding DB file, it works normally.

Within a given folder, files within some subfolders work just fine, while other files get these errors.

I'm very cautious about these files. I was tempted to just delete them and then download the corresponding DB file, but I get the message: "Delete [filename]
from your Dropbox account and all devices?"

For reading an orphaned file, I just download the DB file into a scratch folder and get the information I want. Updating an orphaned file usually requires creating a new folder and keeping the new copy in that.

Megan

Hey @xmarc999 let me jump in here!

I wonder if you get the same error if you manually try to change the files from online-only to available offline.

You should be able to right click on a file/folder, and change its status that way.

xmarc999

Megan, thanks for the thought.

Unfortunately, that just results in the "Couldn't communicate with a helper application.
Try your operation again. If that fails, quit and relaunch the application and try again" error message.

If I try to move the file to the Trash, I get

"Delete [filename] from your Dropbox account and all devices?
If you just want to save hard drive space on this computer, cancel and make it
online-only."

Now I'm curious. I tried each of the right-click options.

Copy Dropbox link - nothing

Share... - nothing

Transfer a copy... – opens the Transfer dialog. I can type in an email address. When I click “Send,” I get “Couldn’t complete your transfer.”

Make available offline – “Couldn’t communicate with a helper application.”

View on Dropbox.com - nothing

Sync next – Opens the Transfer dialog. ?!?!?!?! Try it again. Nothing.

Version history - Opens the Transfer dialog. ?!?!?!?! Try it again. Nothing.

Get signatures – nothing

Sign yourself - nothing

Manage file access - nothing