Calendar Search by Category not showing expected results

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JLH

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Outlook version
Outlook 2010 32 bit
Email Account
Exchange Server
I have a user who has all of her calendar items categorized by her clients. When she tries to search for all items by Category, the results are next to nothing, even though we can see there are 5 items just in this week's calendar. We have gone through the troubleshooter to make sure Search and indexing is working, but that did not make a difference in the search results (it did, however, make the Categorized button not greyed out). We recently upgraded from Outlook 2007 to 2010 and she had categories set up in the old version. What can I look at next to get her search function to work properly?
 
No, in fact, the Search feature did not find the newly categorized item. In fact, at that point, Outlook just sat there 'Searching' for minutes until we closed the search box.
 
In Outlook, I have categories set for my calendar items. When I try to Search my calendar using the "Search all Calendar Items" box and then try to click Categorized, that button is greyed out on the ribbon. Why isn't this availble to me, but it is for others in my office?

Are newly categorized items found in the category search?
 
This is in an Exchange mailbox, correct? Categories are goofy in IMAP and Outlook.com/Hotmail accounts, but it should work in Exchange.

Based on your other problems, it sounds like either search or categories are messed up. You can try rebuilding the search index and resetting the view.

I'll see if I can find other causes of categories button being disabled.
 
Restarting outlook with the cleancategories switch then using Upgrade to color categories might also work, but you'll need to fix the colors. Outlook will assign random colors.
 
How do I restart Outlook with the cleancategories switch? How do I Upgrade to color categories?
 
Close Outlook.

In Start menu search field (Win7) or in the Run command (Windows key + R), type or paste

outlook.exe /cleancategories

and press Enter to start outlook.

Upgrade to color categories: right click on the name of your data file, which is usually your email address.

Choose Properties then click the button to upgrade color categories.

How to Upgrade to Color Categories - Slipstick Systems
 
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