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Outlook not indexing items

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Good morning. I have been dealing with a particularly rough issue for weeks now and I thought it might be time to reach out for additional input. The user is on Win8.1 and using Office 365. He is about a two hour drive from me so getting hands on the machine (Toshiba laptop, perhaps two years old I5, 4G Ram) is possible but more difficult.

The original issue was 100% HD usage. I won't go into great detail here but suffice it to say that after spending about a week on the issue I decided to "refresh" his OS.

This seems to have resolved the original issue. However, now he is having an indexing issue. I reinstalled Office 2013 and began to rebuild his local cache of emails. After a few days I got a call that searching is not working correctly. I look and there are over 60000 items waiting to be indexed. I have tried everything I could...


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