Moving the Home folder to external drive..... Catalina nightmares...

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I have 2012 MacBook Air. Since I have quite a bit of music, video, and documents in those folders I really needed the additional space, so I used a symbolic link to point to my home folder on my external drive. After the catalina upgrade I started noticing the Documents folder in the sidebar stopped pointing to my external drive folders. Which I eventually figured out it had to do with the automatic iCloud storage for desktop and documents folders.

I disabled iCloud got the files located back on the Macintosh HD. I re-did the symbolic link to point to my home folder to the external drive, restarted, and tried to log back in, but I got "You are unable to log in to the user account "xxxx" at this time. Logging in to the account failed because an error occured." So I used my Troubleshoot admin account I had previously created to log back.

BTW, the Troubleshoot account is a vanilla admin account residing on the internal Mac HD. Over the past 15 hours, I've re-install the operating system, created an alias home folder on the external drive, change the home folder location via Users & Groups advance options, and retried the symblolic links, I done several iterations of those various methods with no luck. Don't know what changed, but I finally have it quasi-working via location change method using the Users & Groups advance options.

However, I'm only able to log into my account after I log into and out of my "troubleshoot" account. If I try to log into my USER account after a shutdown and/or restart I still get the "...unable to log in..." message. So after each restart/shutdown I must log in and logout of the troubleshooting account first. Any ideas on how to fix so i dont have to log into my internal HD account (troubleshoot) before logging into my USER account.
 
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Any special reason for relocating your whole "Home" folder and not your music/videos.
I've used symbolic links quite a lot but I always leave my home folder on the boot drive and link to the other stuff. Typically, my Music, Documents and other large files. I've done this from Yosemite to Mojave with no issues.
 
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Here's a little tool that might help you.
 
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I also just keep the media files on an external drive. I link those files to the Music, Podcasts, and TV apps.
 

Slydude

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First, kudos for setting up a separate "troubleshooting" account kept clean and only used in emergencies. I wish more users followed that advice.

I first read about users doing this in the early days of OS X. I'm going to mention a few things you might have already checked. Based upon what I read at the time, here are a few things that could be causing problems:

1. Is the external drive on at the time you are trying to log into your account? I'm wondering if the external drive has fully spun up when the OS needs to access it.

2. Since you can log in to one account but not the other one, I wonder if something is putting the drive to sleep in one account but not the other one.

3. I assume you've checked the external drive with Disk First Aid.
 

Raz0rEdge

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I'll third that you should only move your Music/Videos/Pictures folder to the external drive. In my case, I didn't even bother moving the Music folder that's in my home folder, rather I created a totally new iTunes/Music library that points to the external (in my case NAS folder) that contains all of my music.

With that in place, I just mount the NAS drive to /Volumes/Music and the library accesses it without any issues.
 
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Any special reason for relocating your whole "Home" folder and not your music/videos.
I've used symbolic links quite a lot but I always leave my home folder on the boot drive and link to the other stuff. Typically, my Music, Documents and other large files. I've done this from Yosemite to Mojave with no issues.
Well the main reason, I only have to create 1 symbolic link versus several.... I will definitely look into this solution to see if it will work... Thanks!
 
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I also just keep the media files on an external drive. I link those files to the Music, Podcasts, and TV apps.
Yep, I will try this solution, link to the various subfolders, ie. Music, documents, podcasts, etc., instead of just the home folder... Thanks
 

Slydude

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With that in place, I just mount the NAS drive to /Volumes/Music, and the library accesses it without any issues.

It never occurred to me to do things that way. I'll have to look into exactly how to do that.

I currently have my music on an external drive that sits in an enclosure that's always on. For a while, I had the music on an external drive attached to a Time Capsule. The problem was I kept forgetting to mount the drive before launching iTunes. I solved the problem by creating something in Automator that mounted the drive and then launched iTunes when I double-clicked the icon.
 
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Thanks everyone for your help, I got it to work, by creating symbolic links for the individual sub-folders, i.e. documents, movies, music, downloads.... Thanks again!!!
 
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It never occurred to me to do things that way. I'll have to look into exactly how to do that.

I currently have my music on an external drive that sits in an enclosure that's always on. For a while, I had the music on an external drive attached to a Time Capsule. The problem was I kept forgetting to mount the drive before launching iTunes. I solved the problem by creating something in Automator that mounted the drive and then launched iTunes when I double-clicked the icon.
Sly, the easiest way I found to do that mount automatically is to first mount it manually, then drag it to the "Login items" in System Preferences/Users & Groups/<<my account>>. That way, it mounts when I log in and is just *there* when I want it.
 
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BTW, when I say "Music" I am not only referring only to iTunes. As mentioned previously by others there are several apps that allow you to re-locate your files. iTunes and iPhotos come immediately to mind. However there are others, such as Logic Pro and many "music" apps that don't. Using the app is preferable, but there are many cases were you can't.
 

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