The worst feeling for a geek:
This has happened to me twice now: upgrading Mac OS X from one release to another and after the dust settles, the search function in Outlook 2011 totally breaks and always returns "no results". As we all know, email sucks and being able to deftly search through that mound of crap in your mail client is the only thing that makes it somewhat bearable.
When I upgraded from 10.8 to 10.9, I was the guy in the cartoon above. I had to resort to uninstalling and reinstalling all of Office to get this repaired. Urgh.
Well, I just upgraded from 10.9 to 10.10 and lo, the same problem with Outlook search. However this time my karma must be right topped off because I found the solution buried in a message board after an hour or so of searching.
The post is from the macrumors.com forum and exactly described the issue and how to fix it on my machine. As stated, the permissions on my Microsoft Office 2011 directory allowed only my account to open the directory:
jknight@mac:~% ls -ld /Applications/Microsoft\ Office\ 2011 drwx------ 11 jknight wheel 374 12 Feb 12:06 Microsoft Office 2011/
The fix (with the typo in the chmod command corrected from the original post):
sudo chown root:wheel "/Applications/Microsoft Office 2011" sudo chmod 755 "/Applications/Microsoft Office 2011"
And then, as the posting says, have Spotlight reindex the drive:
sudo mdutil -a -i off sudo rm -rf /.Spotlight-V100 sudo mdutil -a -i on
After letting Spotlight rebuild its index, searching in Outlook was back to normal.
Now whenever I go to 10.11 I can hopefully save myself an hour of searching to get this fixed.