How can I synchronize several GBs of emails on two computers?

I think the point of the matter is that you already have several gigabytes of email that is only going to grow. Now is the time to look at moving all your mail to to an IMAP server and letting it continue to grow on that, rather than trying to keep to separate multiple gigabyte email stores synced.

I'm in the exact same situation, using Outlook + Cloudmark as well. I run Windows XP, have enabled Remote Desktop connections, and when I want to access email from my laptop I connect back to my desktop machine using the Remote Desktop Client. As long as the connection is fast enough, it's just like being at my desk. Cons: This requires me to keep the desktop machine turned on whenever I think I may want to access my email, which is a waste of electricity. I had to puncture my firewall to let RDC connections through; this is a security risk, though I believe RDC traffic itself is encrypted. Some ISPs may not allow your home machine to act as a server in any fashion at all. It helps if your laptop's screen size matches your desktop screen size, to minimize window resizing. When I can't connect back, I use a backup of the PST files on the laptop and my ISP's webmail interface to access newer email. I'm sure others will discuss the possibility of putting all your email on an IMAP server.

IMAP.

I would: 1. export your email out of Outlook 2. import it into second computer client 3. turn on "save email on server" in both email clients and set it to only delete messages after a week or so, long enough for you to have had a chance to check mail on both computers. 4. check your email on both computers, get all new mail on both. 5. be happy. I don't have two computers but I have a home and a work computer and this is what I do. It works perfectly. Keep in mind that 9GB of old email will probably slow down the performance of any email client. I'd just keep the outlook exports on disk and only import them if I really really need something.

IMAP IMAP IMAP. 4-5 GB is nothing for IMAP.

I have been using the http://www.slipstick.com/outlook/sync.htm#briefcase for several years now and it works well. It helps to Archive old emails to a seperate .pst which can reside on both computers, to minimize the sync time.

For those recommending IMAP, are there any tips for providers? My home computer is on a cable connection with limited upstream bandwidth so I probably don't want to host it myself. Most of the providers I have looked into charge substantial money for 4-5 GB plus of storage (and for some, it looks like just uploading my stuff to start with will incur bandwidth overcharges). Also, currently Google Desktop does a great job indexing my Outlook email. Would fast search be an option for IMAP?

I'd agree with the IMAP suggestions, but isn't Outlook's IMAP support crippled in order to encourage you to use Exchange server? As I recall, thinks like filtering rules didn't work. Also, I think you were limited to one IMAP mailbox per e-mail profile.

Im curious on how somoene with tons of PSTs or .msg files is giong to be able to push them to a mail server. The format is wrong and this would involve more costs to have a mail admin do the transfer. Then hosting. The transfer itself is in the gigabytes, which will probably add some kind of penalty for bandwidth use. Second the remote desktop solution. If your machine isnt XP Pro then you can get away with using VNC. Or properly archive your old mail onto a DVD or external hard drive. Keep only this years mail in the client. When you need the old stuff just mount the pst files. Not to mention that windows machine of yours will someday die and now you have an incentive to do proper backups.