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It’s really not that difficult, depending on how many Sent emails you have anyways.  But here I go jumping into the solution without an explanation:

A client of mine wanted to use Gmail to access her company emails, so we set up her account through POP3 in her existing Gmail account.  Easy.

But, she also wanted to be able to see all of her old Sent emails, it would just make searching for things much easier.  Yes from now on her new Sent emails will show up in the Sent folder in Gmail, but her old ones don’t get automatically imported when POP3 is initially set up.  What to do?

Here’s what:

  1. Create a new folder in Gmail, something like Old Sent for example
  2. Go back to whatever email program you were using previously, the place where all your old sent emails are, and move them all into the Inbox.
  3. Poof!  All of those emails will now get sucked over to Gmail, but of course they’ll be sitting in the Inbox so we’ve still got one more step left…
  4. Search for all those emails that were sent from you, then move them into your Old Sent folder.

Ta da!

A bit of a hassle, but really not that big of a deal.  You have to keep in mind that Gmail can only transfer 250 emails at a time so it might take some time, but if you don’t have too many it’s not that bad.  If you look at the Accounts section in Gmail settings you’ll see the progress of the transfer so you can keep an eye on it.