Search Issues in Outlook
Check Indexing Status by searching something and then click Search Tools and find Indexing Status.
Make sure it says 0 or wait for it to get down to 0 until you search again. This is indexing all your emails.
If you still don’t see what you are looking for then go to File and then find Options. Outlook Options Opens like below and make sure you have what is below in the screen shot.
Outlook 2013 caches only 12 months of data by default – Article 100663
- Navigate to File | Info | Account Settings | Account Settings…
- Click on your account and select Change.
- Move the “Mail to Keep offline” slider to your preference. You can select caching for 1 month, 3 months, 6 months, 1 year, 2 years, and “all”.
For more information, please see: http://support.microsoft.com/kb/2733062