I have been reasonably pleased with Obsidian as my note-taking app so far. The interface is minimal and gets the job done, even if the UI doesn’t look at all native whether on Mac or PC.
I’ve been using it primarily on my Windows 11 PC, as that’s my main machine, but have also used it on the iPad (no issues) and Mac (no issues, but with a big fat asterisk, as I will explain right after this parenthetical).
Where I have run into problems is with the sync when using iCloud Drive.
My main vault (folder) for Obsidian is on iCloud Drive, and it works fine on the PC, saving and updating seamlessly. If I open the vault on the Mac, it also works fine there (as expected, since iCloud Drive is an Apple service).
The problem arises after a few specific steps when using Obsidian:
- Access files in vault on PC
- Access files in same vault on Mac
- Access files in same vault again on PC
When Step 3 happens, Obsidian will pop up a message saying it is downloading files or indexing files. The latter is a one-time operation, per the pop-up.
Downloading files happens each time when a file is presumably changed in Obsidian on another machine. Note that I tend to close Obsidian on one platform before accessing its vault on another, though this is not strictly speaking necessary. The issue happens when I do not have the vault in question open before Step 3. I haven’t tested with the vault still open on the Mac before opening it back up on PC.
After downloading, the vault on the PC will now show the original file, along with one or more duplicates, with (1), (2) etc. added to the filenames. These files will not open and clicking on them will pop up the Automatic file downloads dialog again, like the circle of life except in this circle nothing actually happens and everyone probably starves. It’s a mess. Here’s a shot of how the file appears in the vault list:
If I open the Obsidian folder in iCloud Drive where this vault lives, Windows 11 will indicate that it has a sync pending. The contents, as expected, reflect what Obsidian is reporting:
Double-clicking one of these files will try to open it in iA Writer, which is set as my default Markdown editor in windows. This dialog appears:
If I return to the vault on the Mac, the two files are gone. They don’t show in Obsidian, and they are gone from the related vault folder in iCloud Drive. Something is clearly happening when the vault is accessed on the PC after being accessed on the Mac where the sync is failing. Maybe it’s a limitation of iCloud Drive. I’m not sure.
I tried a few experiments with new vaults, and found I could replicate the buggy results easily.
My current solution has been to create a folder on the PC and share it over the local network with the Mac. This seems to be working so far and has the added security of keeping things off the internet. This means I won’t be able to access the vault from the iPad, but that’s an acceptable loss.
I want to blame Apple for this, but I’m not sure who the real culprit is. It does make me hesitant to use iCloud Drive for anything other than basic file storage, though–certainly not for file-sharing. Part of me wants to dig deeper into this to determine the cause, but working on the file shared locally through my own network is probably a better solution, anyway. If this also blows up, I’ll update this post.
In conclusion, technology has a ways to go. I’m pretty sure Steve Jobs would be yelling at someone right now if he were still alive.
UPDATE, May 26, 2022: Since I have forsaken using Obsidian on the iPad, I decided to move the main vault to OneDrive, where in the subsequent months it has worked without issue on both Mac and PC. So now I am a bit more willing to give Apple the stink eye.
