Obsidian iCloud Sync in 2026, Including the Windows Problem

I sync Obsidian to two MacBook Pros, a Windows desktop, an iPad, and an Android phone, and I pay nothing for it. iCloud is not how I do it. I wrote up every method I know of in my full guide to syncing an Obsidian vault across devices, and iCloud got a short section in that post with a warning attached, because the moment an Android phone enters the picture iCloud is done.

But that pillar post never had room to explain the part people actually get burned by. So this is the long version. How to set iCloud sync up properly, what the Apple-only happy path looks like, and the specific ways iCloud Drive on Windows starts leaving random markdown files around your vault.

• Who Obsidian iCloud Sync Is Actually For
• How to Create a New Obsidian Vault in iCloud
• How to Move an Existing Obsidian Vault to iCloud
• The Mac, iPhone, and iPad Happy Path
• The Setting That Quietly Destroys Your Vault
• The Windows Problem
  • The Workaround That Actually Respects the Problem
  • When To Just Not Do It
• Obsidian Sync vs iCloud
• Is Obsidian iCloud Sync Encrypted?
• Cleaning Up the Duplicates You Already Have
• Frequently Asked Questions
• The Verdict

Who Obsidian iCloud Sync Is Actually For

iCloud is the best free option in exactly one situation: every device you touch has an Apple logo on it.

Mac plus iPhone plus iPad is close to zero configuration. Obsidian on iOS has a first-class iCloud option built into the vault creation screen, which is more than you can say for Dropbox or Google Drive on that platform.

Everywhere else it gets worse. Windows is possible but unreliable, covered in detail below. Linux has no official iCloud Drive client at all. And Android is not possible in any way I would recommend to a human being, because there is no iCloud Drive client for Android that syncs a folder to local storage, and Obsidian on Android needs a real local folder. That is why my own vault lives in Dropbox with Remotely Save handling Android. My phone is the constraint that decided the whole architecture.

If your phone is an iPhone and your desktop is a Mac, stop reading comparison posts and just use iCloud. It is free, it is already on, and it works.

How to Create a New Obsidian Vault in iCloud

Two completely different procedures get searched for here, and people mix them up constantly. Creating a fresh vault in iCloud is the easy one. Do this first if you are starting clean.

On iPhone or iPad:

1. Open Obsidian and tap Create new vault.
2. Give it a name. Make it something you will recognize in Files.
3. Turn on Store in iCloud.
4. Tap Create.

On Mac:

1. Open Obsidian and choose Create new vault.
2. For the location, browse to iCloud Drive and pick or make a folder there.
3. Create the vault.

On disk, the Mac path is ~/Library/Mobile Documents/iCloud~md~obsidian/Documents/, which shows up in the Files app as iCloud Drive > Obsidian. That is where the iOS app puts vaults, and it is worth knowing because it is the folder you will be pointing other tools at later. Obsidian’s own docs are direct about this: vaults should live inside the Obsidian folder in iCloud Drive. A vault you drop somewhere else in iCloud Drive will sync between Macs fine and then fail to show up in the iOS app’s vault list, which is a confusing hour of your life you can skip.

How to Move an Existing Obsidian Vault to iCloud

This is the one that goes wrong. The instinct is to drag your vault folder into iCloud Drive and open it. Do not start there.

1. Back the vault up first. Copy the entire folder somewhere outside any sync service. A zip on your desktop is fine, and it is the only thing standing between you and a bad afternoon.
2. Close Obsidian on every device. Not backgrounded on your phone. Closed. Two clients writing into a folder during an initial upload is how you generate conflicts on day one.
3. Create a new empty vault in iCloud using the steps above, with the same name as your existing vault.
4. Move the contents of your old vault into that new iCloud folder. Include the hidden .obsidian folder if you want your settings, themes, hotkeys, and plugins to come along. On Mac, Cmd + Shift + . toggles hidden files in Finder.
5. Wait for the upload to finish completely before opening Obsidian anywhere. Watch the iCloud status in Finder’s sidebar. Rushing this is the whole problem.
6. Open it on your Mac first, let plugins load, then open it on iOS.

On a big vault, leave the attachments out of the first pass. Sync the markdown, confirm it works, then move the images. Markdown files are tiny. Attachments are what blow up the initial sync window and give conflicts room to happen.

The Mac, iPhone, and iPad Happy Path

Once the vault is in place, the Apple-only setup genuinely is the low-maintenance option. Edits show up on the other device in a few seconds when both are awake and online. Obsidian’s own settings sync along with the vault because .obsidian is just another folder, so if you have gone deep on installing Obsidian plugins you do not have to set them up again per device.

Two habits keep it that way. Let one device finish syncing before you start editing on another, because sync services do not have opinions about which version of a paragraph you meant. And never run a second sync system on the same vault. Not Obsidian Sync on top of iCloud, not Dropbox pointed at the same folder, not a Git plugin committing every two minutes. Two sync engines fighting over one folder is the most reliable way to lose notes, and it is self-inflicted every time.

The Setting That Quietly Destroys Your Vault

Turn off Optimize Mac Storage for iCloud Drive, or at least understand what it does before you leave it on.

When macOS decides you are low on space, it evicts the local copies of files it thinks you are not using and leaves a placeholder with a little cloud icon. For photos, fine. For an Obsidian vault, not fine. Search, graph view, and backlinks all depend on files actually being present on disk. An evicted note is not a note. Searches come back short, links look broken, and nothing warns you that half your vault is currently a stub.

The setting is in System Settings > [your name] > iCloud > iCloud Drive. If you need it on for storage reasons, open iCloud Drive in Finder, control-click the vault folder, and choose Keep Downloaded to exempt it. Windows has the same concept with a different name, and it is worse there, which is a good segue.

The Windows Problem

Obsidian’s own documentation says flatly that iCloud Drive on Windows may lead to file duplication or corruption. When the people who make the app warn you off a sync method, that is worth more than any blog post, including this one.

iCloud for Windows exists. You install it from the Microsoft Store, sign in, and get an iCloud Drive folder in File Explorer. You can point Obsidian at a vault inside it. It will appear to work. Then, over days and weeks, these things start happening.

Placeholder files instead of real files. iCloud for Windows does on-demand downloads the same way OneDrive does. A file with a cloud icon next to it is not on your disk. Obsidian tries to read it, and depending on timing you get an empty note, a failed read, or a plugin that throws. Vault-wide operations like search and Dataview queries are the worst hit because they touch everything at once. You can fight this by right-clicking the vault folder and choosing Always keep on this device, which pins it locally. Do that before anything else if you are going to attempt this at all.

Duplicate files with numbers appended. This is the classic symptom and the reason people search for this problem. You end up with Meeting Notes.md and Meeting Notes 2.md, sometimes several generations deep. It happens when the Windows client and another device both write a file before either has seen the other’s version. iCloud does not merge and it does not prompt. It keeps both and renames one.

The .obsidian folder taking damage. Your config folder is a pile of small JSON files that get rewritten constantly as you use the app. That write pattern is exactly what a lazy sync client handles worst. Corrupted workspace.json, plugin settings reverting, hotkeys resetting, community plugins disabling themselves. If your Windows machine keeps forgetting your setup, this is why.

Sync that just stops. The client parks in a pending state and stays there. No error, no notification, just a folder that stopped updating while you kept typing into it.

Timing that encourages all of the above. iCloud on Windows is slower to propagate changes than it is between Apple devices. A longer window between “I saved” and “the other machine knows” is a bigger window for conflicts.

The Workaround That Actually Respects the Problem

The fix that works is to stop letting Obsidian and iCloud touch the same folder.

Keep your working vault in a plain local folder on the Windows machine, somewhere iCloud cannot see. Then run a separate process that syncs that local folder to the iCloud copy, with real conflict handling. Obsidian only ever talks to fast local disk, and the sync layer deals with iCloud’s nonsense on its own schedule.

gursimar/obsidian-icloud-windows-sync does exactly this. It is a Python three-way sync engine that tracks the local vault, the iCloud copy, and a history snapshot so it can tell the difference between “this file changed here” and “this file changed on the other side.” When both changed, it keeps the newer one by modification time and saves the loser as a _CONFLICT_<timestamp> file rather than silently picking a winner. It uses atomic writes and a stabilization delay so it is not reacting to Obsidian’s autosave mid-keystroke. The README is explicit that it must run natively on Windows and not under WSL, because iCloud placeholder files behave incorrectly when accessed through WSL.

That is a real answer, but be honest with yourself about what it is. It is a Python script you have to configure with a YAML file, keep running, and troubleshoot when it stops. If that sounds like a project rather than a solution, it probably is one for you.

When To Just Not Do It

If your setup is Windows plus iPhone, iCloud is the wrong tool. You are picking the option that is worst on your primary computer for the sake of convenience on your phone.

Dropbox with Remotely Save covers Windows and iOS without any of this. So does Syncthing if you want nothing in the cloud at all. Obsidian Sync costs money and handles it. Any of those is a better use of your evening than fighting a sync client that is not designed for the write pattern of a notes app.

I keep a Windows desktop in my rotation. I have never once been tempted to put my vault in iCloud on it.

Obsidian Sync vs iCloud

The honest comparison, since “obsidian sync vs icloud” is what a lot of people are really asking.

Four dollars a month is the price of not reading this article. If you use Obsidian daily and your devices are not all Apple, that is a rounding error against the time any free method will cost you. I do not pay it, but I also enjoy this kind of problem, which is not a normal thing to enjoy.

The version history row is the one people undervalue. iCloud can restore some files some of the time. Obsidian Sync keeps per-note history that understands what a vault is. The first time you need it, that gap is enormous.

Is Obsidian iCloud Sync Encrypted?

Yes, but probably not in the way you are assuming.

iCloud Drive is encrypted in transit and encrypted on Apple’s servers by default, and Apple holds the keys. That means Apple can access the contents and can be compelled to hand them over. Standard data protection is the default on every account.

Turning on Advanced Data Protection moves iCloud Drive to end-to-end encryption, so only your devices hold the keys. It is in System Settings > [your name] > iCloud > Advanced Data Protection on a Mac, and the same path under Settings on iOS. The tradeoff is real. Apple makes you set up at least one alternative recovery method first, either a recovery contact or a recovery key, because once it is on Apple does not have the keys to help you. Lose your recovery methods and the data is gone. That is the entire point of it.

Obsidian Sync is end-to-end encrypted by default with no configuration. If your vault holds anything you would call sensitive, that difference matters more than the price difference does.

Cleaning Up the Duplicates You Already Have

If you got here after the fact, the vault is already littered with numbered copies. Work in this order.

Close Obsidian everywhere, let iCloud finish syncing, and copy the whole vault out to somewhere iCloud does not control. Then find the offenders. On Mac, from the vault root:

find . -name "* 2.md" -o -name "* 3.md" -o -name "*conflicted copy*"

On Windows, in PowerShell:

Get-ChildItem -Recurse -Filter "* 2.md"

Diff before you delete. Most numbered copies are identical to the original and safe to remove. Some contain the only copy of a paragraph you wrote:

diff "Meeting Notes.md" "Meeting Notes 2.md"

Merge what matters, delete the rest, fix any internal links that pointed at the duplicate, then fix the cause or you will do this again next month. Fixing the cause means taking the Windows machine out of the iCloud path, or moving the vault to a method that handles conflicts properly.

You can also automate the finding part. Obsidian Cleaner, one of the plugins I had Kiro build for me on free monthly credits, surfaces conflicted copies, numbered duplicates, and zero-byte markdown files as a checklist you can review before deleting. I built it because I kept hitting this, which tells you how common the problem is across every sync method, not just iCloud.

Frequently Asked Questions

How do I sync Obsidian with iCloud? On iOS, enable Store in iCloud when you create the vault. On Mac, put the vault in ~/Library/Mobile Documents/iCloud~md~obsidian/Documents/.

How do I connect Obsidian to iCloud on a vault I already have? Close Obsidian everywhere, create an empty iCloud vault with the same name, and move your files plus the hidden .obsidian folder into it. The order matters more than the steps do.

How do I move my Obsidian vault to iCloud without losing anything? Back up first, and wait for the initial upload to finish before you open the vault on a second device. On a large vault, sync the markdown first and the attachments second.

Does Obsidian iCloud sync work on Windows? It runs, but it is unreliable. If you must do it, keep the working vault in a plain local folder and mirror it to iCloud with a tool like gursimar/obsidian-icloud-windows-sync rather than letting Obsidian edit inside the iCloud folder.

Is Obsidian iCloud sync encrypted? Encrypted in transit and at rest, but Apple holds the keys unless Advanced Data Protection is on. Obsidian Sync is end-to-end encrypted by default.

Can I sync Obsidian to Android with iCloud? No. Use Dropbox with Remotely Save, Syncthing, or Obsidian Sync instead.

The Verdict

iCloud sync for Obsidian is genuinely good and genuinely free, right up to the edge of Apple’s ecosystem, where it falls off a cliff with no railing.

All Apple, all the time: use it, it is the right answer and you can stop researching. Windows in the mix: it is a maintenance project, and you should either run a real sync layer on top of it or pick a different method entirely. Android anywhere in your life: it is not a choice you have.

I landed on Dropbox and Remotely Save because of an Android phone, and I have no regrets about it, though I did spend a weekend getting there. The methods are not ranked by quality. They are ranked by which devices you happen to own, and the honest advice is to pick based on your worst device rather than your best one.