Obsidian Sync - Locally encrypted files

Things I have tried

I have experimented with the iCloud sync function. I have not experimented with Obsidian Sync because I don’t want to pay just to test things out.

What I’m trying to do

I am trying to use Obsidian across a few devices (iPhone, iPad, personal desktop, work laptop). For my work laptop (which I use most often), I am keeping the vault on an external drive because I don’t want my files on the laptop hard drive. However, we use Symantec Endpoint Encryption, which automatically encrypts any file created or transferred onto an external drive from the machine .

This is normally a nice feature, and in fact, I’m happy to have the vault encrypted “at rest” when it’s on the drive. What I am struggling with is how to sync the files across devices. Using iCloud, the files are sync’d in their encrypted state, so when they are opened in Obsidian on another device, they appear as gibberish. (Symantec has its own file explorer to decrypt and open/copy the files.)

My question is how Obsidian Sync operates: does it sync files to Obsidian’s servers while they are open in the program (and therefore not locally encrypted), or does it sync saved files from the vault folder similar to iCloud? I am hoping it’s the former.

I think there is a big confusion in this post.
I can tell you this.
Files open in the program = Files in the vault folder.

Obsidian to work needs access to an unencrypted folder with full filesystem primitives support.

How is the encrypted folder stored? How is the decrypted folder deduced from the encrypted folder?
It is possible that the encryption solution your company uses stores files encrypted and then creates (mounts) virtual unencrypted files for you to work on. I don’t know.

There are too many variables here. Depending on how things really work in your company
Obsidian can work perfectly
Obsidian can work but malfunction
Obsidian can’t work.

This is beyond what we can offer support.
You can buy a single month of sync and try.

Note: there is also the side discussion that if it does work and you do it, you might violate your company policies.

Thanks for the reply. Unfortunately, I can only speculate on whether it’s mounting a virtual file, but I can tell you that I have no issue opening the vault and editing files in Obsidian while using the laptop. Somehow Symantec is automatically decrypting files while they’re open. I didn’t realize there was a monthly option–I’ll buy a month and report back.

Okay, here are the results of my $5.00 experiment:

Take it for what it’s worth; this is specific to Symantec Endpoint Encryption, and I’ll note again (as I did above) that Symantec automatically decrypts working files on the machine that has the software installed. Decrypting files on other machines requires using a file explorer called RemovableMediaAccessUtility.exe.

I created a vault on the iPad and set it up with Obsidian Sync. I then created an empty vault on the laptop external drive (which is being automatically encrypted by Symantec) with the same name and set it up with Obsidian Sync also.

  • Creating new files on the iPad and then opening them on the laptop - works. This was expected.
  • Creating new files on the laptop (which are being automatically encrypted when saved) and then opening the sync’d files on the iPad - works. So whatever Symantec is doing to encrypt/decrypt, Obsidian is sync’ing the decrypted version while the program is open.
  • Copying a folder of encrypted notes from another vault into the sync’ing vault, then opening those files on the iPad - works, regardless of whether I had first opened or edited the file on the laptop.
  • Copying other file types (I tried .pdf, .jpeg, .csv, .xlsx) into the laptop vault folder–those files are then automatically encrypted–and opening them on the iPad - works, again whether or not they are first opened or edited in Obsidian on the laptop.
  • Closing Obsidian on the laptop, copying encrypted .md files from another vault folder, editing some of them in Notepad, then opening back up Obsidian, letting them sync, and then opening them on the iPad - works.
  • I ran into one issue with a couple of .md files that I had created earlier on that I was unable to decrypt on the iPad or the laptop. If I recall, they were files that were created by Obsidian when I created a [[wikilnk]] and clicked on it, but I had never added content to them. This doesn’t seem like a sync issue. Luckily, no content was lost (cause it didn’t exist), and when I replaced the encrypted data with text, the new text sync’d without issue.

That’s about all I was able to come up with in terms of tinkering. I’d say this is exactly how I hoped this would function. It’s kind of the best of both: locally encrypted files on a portal hard drive, and E2E-encrypted sync to other devices.

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