Obsidian, iCloud and general files stuff

I’ve got a ‘problem’ that I’ve been trying to solve for some time, and would appreciate some advice on - even if that advice is it ain’t really a problem, move on!

Background - I use Obsidian for all sorts of things (notes, project management tracking, articles, resources etc.), nothing too taxing. I should add that although I like the app, I am always keen to find a native Mac/Apple solution, and keep dipping into stuff like Noteplan, Agenda, Notebooks, just in case they work for me, but have found some pinch points with each so far…

I use iCloud to store the Obsidian vault, and the vault (i.e. folders in iCloud) is structured around the PARA method. Everything goes in there - notes and all files (even if they’re not directly referred to within Obsidian, say via a note, link etc.) It’s my primary storage area and works well in it’s own right, available everywhere to all my devices.

This means my iCloud folder structure/Obsidian vault is quite large (it’s all related to work). That isn’t necessarily a problem until I come to use Obsidian on both the iPad and iPhone (fine with my MacBook Air). Because of the various files within the vault, Obsidian struggles when trying to index the iCloud folder, even crashing at times. If I manually wade through the various levels of folders within the Files app and try to ensure everything is downloaded, then eventually Obsidian will crank up and work.

While I know the ‘solution’ is to separate the bulk of ‘files’ from my vault into a separate set, it is very useful having everything together within the a folder-based PARA system.

I’ve also dabbled with using DevonThink as both an overall solution or an adjunct to Obsidian (using Ryan’s excellent plugin) - the issue Ive found with that is DT’s slight unreliability with indexing cloud-based stuff (something I think I’m right in saying they generally advise against).

I could use DT with a folder outside iCloud, but then Obsidian mobile won’t work. I could use Obsidian sync, but then I don’t have the cloud-based folder structure available to all devices/apps - it’s ‘exclusive’ to Obsidian.

Any thoughts or ideas welcome :slight_smile:

It sounds like you’re storing files in your vault that don’t “need” to be there. Why not store them in a separate iCloud folder as to not add overhead to Obsidian? What you’re doing sounds more like a Devonthink or Evernote solution, which Obsidian is not…

I am nor 100% sure but I suspect this is related to how iCloud behaves. Especially on the iPad, the OS decides what you need to keep on the iPad and what should be downloaded on demand from iCloud. The theory is good but in practice it does not work for me.

I have numerous posts on this forum on how unreliable iCloud is , the latest thread is here. In order for Obsidian to work for me on my Macs and Ipads, I have to pay for Obsidian sync. That is the only way I can make it work.

Not sure this helps you

I also pay for Obsidian sync and have come up with a system that I wrote about on the Obsidian forum.

Lots of reported issues with iCloud sync and Obsidian. I’d find a way to ditch that, Obsidian Sync seems like it would work sicne you are already committed to having things out in the cloud somewhere.

Hmmm, I’ve not noticed any issues syncing Obsidian via iCloud. What kinds of problems are people having?

Are you on a VPN? I had similar issues while using a VPN, turning it off temporarily to allow syncing was my quick fix.

How many files are in your vault and what is the total file size? I’m curious.

Try “remotely save” plug-in with obsidian. It will copy and sync your obsidian iCloud to Dropbox/OneDrive etc. Then you can have your obsidian iCloud sync as just the md files, but have it save to Dropbox in whatever folder you want. Then you can use your para system in Dropbox and use Dropbox search.

I am doing something similar but actually syncing the obsidian iCloud to my synology NAS as I like to search obsidian and my pdf (all of which are OCR), and work from windows pc often.


Thanks for the reply. Yes I understand your point, but it is useful to have links within notes to files that are relevant, and liking ‘outside’ the vault can be problematic.

However, given this comment and others, I am trialling having what is essentially a separate iCloud folder for files as you suggest, and utilise DevonThink and indexing, using its linking system to allow notes in the the one folder to have links to files (in the other folder) that work across devices.

My only concern as mentioned briefly in my original post, is the reliability of DT to accurately sync cloud-based files and folders…

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Thanks :slight_smile: TBH, I have found iCloud to be generally very reliable - it’s just that on iOS and iPadOS, ‘it’ decides what is available on those devices (at least initially and for good reason i.e. storage), and this conflicts with what mobile Obsidian needs…

Thanks - useful post!

Hi - thanks for the reply. Not using a VPN…

Well, in terms of raw size, it (was) over 13gb…