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I recently reinstalled Yosemite to fix the notorious WiFi bug, and i have two hard drives, one SSD which i reserve for apps and boot, and the other HDD for data (including user data).

I started up my mac made a user account on the SSD (aside from my original one, this is a safety precaution in case the HDD goes down and i need to log in to an account on the SSD), then i copied my user folder to the HDD and went to the advanced settings for that account and pointed it to the new location on the HDD.

When i logged into my account that now has a home folder on the HDD a screen pops up saying OS X needs to repair your Library to run applications. Type your password to allow this

I type my password but it just pops up again in an infinite loop.

One strange thing to note is four ? symbols on the dock for keynote, pages, and other apps that i haven't had installed (And haven't even purchased).

Why would simply copying the fresh user folder from my SSD to my HDD (both were formatted during install) cause this error?

When i force restart and log into the admin account on the SSD i can point my user folder back to its original folder on my SSD (since i did not delete it) and then log into it and everything is normal (and there are no ? symbols for apps i don't own on my dock either.

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NOTE: I got this same error after upgrading from El Capitan (10.11) to Sierra (10.12), so hopefully this will work for your issue.

Steps I took to resolve this:

  1. Open Terminal and copy the following: "defaults write com.apple.Finder AppleShowAllFiles YES" (do not sudo) and hit return. Then type "killall Finder" and hit return.
  2. Using Finder, select Go > Computer > Macintosh HD > Users > User Folder > User Library. Right click and select Get Info > Permissions
  3. In info Library window, unlock to make changes and ensure there are no other users except User and Everyone. Toggle “Read & Write” to “Read” and back to “Read & Write”. Select the gear icon to apply to enclosed items.
  4. Close all credential prompt dialogs by hitting Cancel until the prompts stop. Reboot your system and the issue should be resolved.
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  • Confirmed this worked for me. The infinite popup I had to keep cancelling until my Mac actually restarted. Also for some reason doing the defaults write didn't show my Library folder but simply right clicking in the folder there is an option to Show Library folder.
    – aug
    Dec 5, 2017 at 7:48

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