Modern webmail providers like Hotmail and Gmail essentially tell you "store it and forget it", meaning to push all your email in there, don’t worry about it and it will be A-OK. Well.. whether it’s really A-OK is up for debate.
Let’s say your in the situation where you’re using a mail client and want to transfer several thousand emails from your computer to a webmail account. This is not an uncommon occurrence. As time goes on, you collect more and more email. And with webmail providers actually telling you to keep it all, you do so.
If using Gmail, the way to migrate a bunch of mail locally to the web is via IMAP with drag and drop. If using Hotmail, same thing, except you use its native DeltaSync protocol via the Windows Live Mail client.
Okay, you’re ready to migrate some mail. So you drag and drop, and.. choke. Gmail spits back an IMAP error. Hotmail spits back a DeltaSync syncing problem.
What happened?
You probably tried to move too much email at once.
This is the part where I get a good chuckle. We have amazingly fast PCs that can do darn near anything. We have lighting fast internet that can handle gigs of video transfer. But to this day you’ll encounter network choke when transferring a bunch of mail. It’s comical.
There are basically three rules when migrating a ton of mail to an internet webmail account:
1. Move your largest emails first
These are the mails you’re going to have the most issues moving. Sort your mail by size with largest first and tackle those before any other consideration.
2. Transfer only 100MB of mail at a time or 100 emails at a time
Why only 100MB? Because anything over that can potentially cause network choke.
Why only 100 emails? IMAP and DeltaSync can synchronize 100 mails at a time easily. You can be brave and try 250, but anything over that and you’ll encounter network choke.
3. Expect the mail client to screw up
Mail clients to this day are pretty dumb, so don’t expect them to do what you want all the time. This is especially true when mass-moving email from local to IMAP or DeltaSync. If you encounter a flub-up, it’s most likely from the mail client having a bad sync. Just try again and the problem clears itself usually. If not, restart the client to reset the mail server connection completely.
There’s also one additional rule: Be patient. You will eventually get all your mail out there, but it’s certainly not something you’ll have done in 5 minutes. ![]()

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