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I am looking for a way to accomplish the following on Monterey (12.6):

In the past I would symlink some Mac OS system folders (Documents, Downloads and Desktop) to folders already synced to a Synology NAS and have the "links" act like the "original Mac OS folders. What I want is to have these files exist on the NAS and not on the local storage: Two Macs, same (synced) files in the the local folders.

For clarification - my question is not about how to sync stuff with the Syno NAS, it's how to have already synced folders act like the original user folders „Documents“, „Downloads“ and „Desktop“

Actual setup: The „SynologyDriveFolder“ is the permanently synced (remote) folder from the Syno NAS sitting somewhere under ~user/ which is holding the remote folders „Documents“, „Downloads“ and „Desktop“ (via the up and running SynologyDrive service). They should act as the „real“ system folders on each Mac to choose from, especially in the „Save as…“ dialogue and I want to place them in the Finder’s sidebar as „the only“ „Documents“, „Downloads“ and „Desktop“ folders (no issue with saying goodbye to the original Mac OS folder icons for the specific folders)

Under Mojave it was super straightforward: Made Symlink of „remote“ folder (in my case ~user/me/SynologyDriveFolder/Documents/), placed Symlink in Macintosh HD/user/me/ and renamed original „Documents“ to something different. Done.

From what I learned (and tried but failed on a test install of Monterey), due to (security) changes made in Catalina or so, nowadays it is not as easy as it was. I did some research but did not find a reliable explanation how to set symlinks (resp. firmlinks I stumbled across) on Monterey.

Can I substitute a folder on the NAS for a local folder in the user's home folder on macOS Monterey?

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  • To my knowledge the changes in Catalina targetted only certain near-root folders required for essential system operation. User data (everything under /Users and indeed most of the visible volume) shouldn’t have been impacted. I’m not able to test locally at this time, but have you ensured iCloud Drive is disabled or is set not to sync Desktop and Documents? In previous macOS installs I recall doing similar shenanigans to my home directory, but that may have been pre-Catalina (it’s been a while).
    – Nebula
    Nov 18, 2022 at 17:15
  • Negative Nebula, iCloud is not active for Files/Folders (as it wasn't on Mojave)
    – nail
    Nov 18, 2022 at 17:18
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    Sudo access may be enough if it’s just the Finder UI preventing you from renaming, have you tried similar command-line steps as discussed here? discussions.apple.com/thread/252363209
    – Nebula
    Nov 18, 2022 at 17:20
  • Why not host the entire user home folder on the NAS? Do you really want two copies and sync or one copy so the system writes to the NAS?
    – bmike
    Nov 18, 2022 at 19:55
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    Documents, Desktop and Library in the user home folder should not be messed with. Create symlinks if you like but don't replace Documents or Desktop. Symlinks of key folders to an external drive risk locking you out of your account if the NAS is not connected.
    – Gilby
    Nov 18, 2022 at 22:45

4 Answers 4

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I use Resilio Sync to sync my Documents folder between my Mac Mini and MacBook Pro.

I also have a Synology NAS, and there is a Resilio Sync app for it.

However, there are other loads of other syncing apps out there.

I think syncing between the three things (whether by Resilio, or rsync, or Chronosync, etc) is probably safer than trying to modify the Documents (et al) folders and making the network drive a 'host' -- particularly if you want to take the MacBook for a walk.

(Technically, Desktop, Documents and Downloads are User folders, not System folders.)

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I personally wouldn't mess with the home folder. A couple apps allow you to locate their "storage" outside the home folder like Photos and Music - so I would move my entire home folder to the external drive / NAS if you can't live with just a couple items outside the local /Users folder which on macOS Monterey (and newer) is at /System/Volumes/Data/Users

Trying other things is more hassle, more debugging, more points of failure than any benefit I've seen or experienced. A few people have pulled it off, but they all had very detailed and long experience in why / how / managing things on both the UNIX and macOS end to succeed.

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    > "I would move my entire home folder to the external drive" Don't try this unless you want to be locked out of your account. I foolishly bought a Mac Studio with a 512GB drive, expecting to symlink in my nice fast Samsung SSD, like I did on my 5k iMac. OSX let me change my user account settings to point to the new folder, but then wouldn't let me log in to that account again. Symlink farms seemed like the best way forward, but 12.6.2 is ignoring some of them. Jan 18, 2023 at 20:25
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My solution: After having made a trade-off between "heavy" tinkering (much more as it was needed under Mojave) to point only some User folders to my NAS versus treating them as "Favorites", I skipped the Symlink part and made them accessible in the Finder like back in the Mojave days: I colored the synced Documents and Download User folders and added them to the Finder sidebar on the iMac ("* Drive" and color is indicating the remote ones). Same on the MacBook. 2 Macs, identical data.

I can quickly choose them in the "Save" dialogues (see screenshot, Safari example), drag stuff around in the Finder and it's still pretty close to the setup I had in the past. Thanks to all!

enter image description here

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My Solution

Line up the two commands in Terminal - you need to be quick to do this as there is a small gap between when you delete the Downloads folder and the Mac creates a new one automatically. If you can just 'up arrow' + return in terminal you can be fast: first do the symlink command: ln -s /path-to-new-downloads-folder-onsecond-HD /path-to-originl-in-user-folder

hit return (nothing will happen)

now give sudo -rm -rf ~/Downloads and do password (fast now!)

up arrow to the ln -s .... line + hit return

If you're fast enough and MacOS didn't beat you to it you have a symlinked Downloads folder that works (Monterey!)

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  • Why not put both commands into one line and separate them by ;?
    – nohillside
    Dec 13, 2023 at 7:16

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