The basic searching of sent emails in Outlook 2010 is hopeless. There is an advanced search feature, but I couldn't seem to quickly make it do what I wanted.
What I wanted was to search for a phrase in the subject and body of all emails sent to a particular recipient. The problem was I couldn't filter all emails to the recipient, then search within those results.
Ordering the sent emails doesn't work either. If I order by "To" I get different formats of their email address. For example if I've sent to "John Smith firstname.lastname@example.org", these variations appear in the sent list
- John Smith (If I've replied to an email he's sent) - SomeoneElse@test.com; email@example.com (if I'd sent to someone else as well, putting someone else first - the first three variations could appear after the semi-colon)
So what I did was build an MS Access database which connects to my Outlook and imports all sent emails (EntryID, Recipient Emails, Subject, Body and DateTime sent).
The recipient email list for each email is key - it has their email address, not their display name.
I then built a searching interface where I can enter part of the email address - this covers all the scenarios above. In addition to this I've added other search fields for subject and body, so I can search for "smithj" in the To field and "sample text" in the body.
I can also put lists in each search field, so can search for multiple phrases/email addresses.
The importing takes a few seconds, but search is pretty much instant. Double clicking a result opens the Outlook email.