Can't save to certain folders in iCloud Drive

Hey Everyone,

I’m having trouble saving files in Safari (and other browsers) to specific folders in iCloud Drive on macOS Big Sur. In the screenshots below, I’m trying to save a generic file to the Obsidian folder in iCloud Drive but it’s grayed out. I can access it from the finder and Obsidian still works. I’ve granted Full Disk Access to Safari as a precaution and restarted the computer to see if this was a blip but still no luck.

Does anyone have any ideas? Here are a couple of screenshots illustrating the problem.

Thanks for anyone/everyone’s help

Wow, that’s what I love about MPU. Even people who have been using Macs for decades can learn things here. I have never heard of this problem before.

It’s not Obsidian, you can’t drop an .html file into the iCloud Pages or Numbers folders with the Finder either. I was able to move an .html page into the Numbers folder using the mv command in Terminal, and it did sync, so it doesn’t seem to be a permissions problem.

My guess is Apple won’t let the Finder do this for some reason that is beyond me, or it’s a bug. But I have no idea how to work around this restriction. Sorry.

Odd coincidence – I was manually rearranging folders in an Obsidian vault today using Finder. Sometimes drag and drop works, sometimes it doesn’t. Cut (⌘X) does not work but copy (⌘C) and paste (⌘V) from one location to the other does work.

I agree, it is not an Obsidian issue. Search Google for “cannot drag drop icloud drive” turns up a lot of reports on this going back years.

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The HTML example I posted above was an example but I discovered the problem with PDF as well which was my original intent. I haven’t tried other file types.

Interestingly, if I have a shortcut to a nested folder in the sidebar, it lets me navigate but then the save button disappears

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I did some further testing using the Numbers and Pages iCloud folders (I don’t use Obsidian). I could not drag a PDF into either folder but I could drag a .TXT file. But when I changed the extension of the TXT file to .MD I could no longer place it into either folder. Copy & paste as @anon41602260 suggested worked with some files but not others.

Finder did allow me to place Excel (.xlsx) files into the Numbers folder but not the Pages folder. However when I changed the extension on the excel file from .xlsx to .txt Finder would move the file into the Pages folder. And it allowed me to change the extension back to .xlsx while in the Pages folder and open the file in Excel. The problem apparently is not the file type, but rather the file extension.

If you really need to move files into these problem folders you could probably cook up a Hazel rule to, for example, rename a .pdf file to .txt, place it in the desired folder, then replace the .txt extension with .pdf.

Problem solved, at least with Obsidian. Here’s a thread on their forum which documented the issue (thanks @WayneG and @anon41602260 for pointing out the drag and drop aspect of this issue).

In short, the app needs to declare what file types it supports and that has an impact on what files can be dragged into the folder. Obsidian had a bug and didn’t allow any files but they’ve since fixed it. It required re-installing the app but the issue is solved.

So it looks like the problem @WayneG is seeing with the Pages/Numbers folders may actually be by design, perhaps for security purposes, although it seems pretty flawed.

Thanks everyone for the help!

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Thank you for tracking that down, @motopascyyy. Following the suggestion in the Obsidian forum thread you linked to, I quit and deleted Obsidian, also deleting some settings files for Obsidian that Hazel suggested could also be deleted. Then downloaded Obsidian and installed it from the DMG. When you delete and reinstall Obsidian you’ll need to tell Obsidian again which folders are vaults, which is no big deal. Vaults store their settings, lists of plugins and their settings, etc., within the vault folder, so reinstalling the app doesn’t affect the data or internal workings of a vault.

I can now work with the vault folders and files from within Finder without getting the weird white “banned” sign popping up when I try to drag files into folders.