This one comes courtesy of reader/listener Travis Finstein. (Thanks, Travis!)
If you’ve made the transition to a Web mail account like Gmail, you cloud computing maven you, then you may be interested to discover that it’s possible to transfer all of your old email from Outlook (or Outlook Express, or whatever) to Gmail (or Hotmail, or Yahoo! Plus) using simple drag and drop. To do so, configure your Web mail account in Outlook (using IMAP if that’s supported) and then just copy mail and/or mail folders from the local account to Gmail. (Note, however, that simply drag and dropping will move mail, not copy. To just copy, right-click and drag and then choose Copy.) This should method should work with any variety of local email applications and Web mail accounts. But here are a few things I do know for sure:
1. IMAP works best. The optimal setup, then, is Outlook to Gmail using Gmail’s IMAP functionality. But this should work fine in Windows Mail, or Windows Live Mail, or whatever.
2. If you have a Hotmail/Live account, download the Outlook Connector to access that account in Outlook for free.
3. If you have a Yahoo! mail account, you will need to upgrade to Yahoo! Mail Plus ($20 a year) to access that account in an email application like Outlook. Unfortunately, that access is POP3-only, so see the next tip.
4. Be careful if you set up a Web mail account for POP3 access. You don’t want to inadvertently download all of your Web mail to the local PC, completely obviating the point of this tip. :)
I used Outlook for many years and had to adopt a pretty Draconian email management system because of the volume of mail I receive. So I used to start a new PST file every quarter. My PST files from 2005 through mid-2007 occupy almost 5 GB of space on my home server and I’ve had mixed results getting that stuff moved up to Gmail via IMAP. In some cases, the PST files are malformed and need to be fixed with a tool Microsoft supplies with Office. In others, the transfers seem to die out partway through and Outlook becomes unresponsive. So I’ve been doing it in blocks of 2000 messages at a time. For me, this is very time consuming, but it will be worth it if I can get all that mail up into the cloud where it belongs.