Move all emails from Windows Live Mail to Google Apps (free) account

I have a user here that has about 250,000 emails that are currently in Windows Live Mail. WLM is running extremely slow (for obvious reasons) and I am thinking the best way may be to move him completely to Google Apps for email. He currently has an apps account, but moves emails from the Google IMAP account to a local folder in WLM. I am thinking the best way to get rid of WLM would be to move all local folders and emails back up to Google. Is this a good idea, and if so what would be the best way to move his local folders and messages? In the past I have simply create the folder structure in GA mail then moved chunks of messages at a time up to the IMAP folder. With this quantity of folders and messages I'm afraid that may be a very time consuming task. Is there an automated way to do this and to ensure that every email gets uploaded?
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My advice for people using Gmail or Google Apps has always been to avoid using a desktop mail client. Google is designed to be used via the web interface. While it does technically have the ability to connect to a few clients (e.g. IMAP, or the Google Apps Outlook Connector), these are clunky and slow, especially on large mailboxes. Also you lose a lot of the real capabilities of Google, such as the searching and the integration with other Google services.

Everyone just gets along better if you keep it simple and just tell them that they HAVE to use the web interface otherwise they'll have a bad experience.

If they insist on using a desktop mail client, they're using the wrong product. Instead of Google Apps, they should be thinking about a Microsoft Outlook + Microsoft Exchange Server solution such as Office 365.

Either way, he should not use Windows Live Mail.


That being said, IMHO to do the migration smoothly, you should first migration from WLM->Microsoft Outlook 2010. This process is fully automated and supported by both applications. I choose Outlook 2010 because it is the latest "mature" version. Outlook 2013 would probably be fine as well but 2010 has been battle tested by the world for several years so I trust it more.

Once all the mail, calendars, contacts etc. are in Microsoft Outlook, you can install the Google Apps for Business Outlook Connector and connect to his Google Apps account. Make sure to configure the connector to sync the ENTIRE mailbox. By default it only syncs the first 1GB which will be problematic down the road.


Then you can use Outlook to import the PST file, and it will pull in all of the contacts, mail, folders, etc.

If you managed to convince your client to go with Office 365, the procedure is exactly the same but you would instead be connecting Outlook to the Office 365 Exchange Server instead of the Google Apps Outlook Connector. Procedure is the same - import the PST file.
The Google Apps Outlook Connector requires Google Apps for Business - the premium paid edition. If he is using a Free edition of Google Apps you'll have to sign him up for a trial of Google Apps for Business. As of today, you can downgrade back to the free edition so long as you do it before the trial expires.
bhilgenkampAuthor Commented:
Thank you for the detailed response. It looks like Google got rid of the free service, so once we would upgrade to the Business service we would be stuck with no option to revert back to free.

I did find a method of importing all WLM into Thunderbird, and then using a piece of software (GWFTB) that would transfer all email from there up to Google. I did not try this method though.

This user was getting a new SSD system drive, and since that upgrade he has said the performance is now acceptable. I know performance will continue to degrade over time as more emails are brought in, but unfortunately he is an owner of the company and I can't force him to use something other than WLM.

I have accepted your answer as a solution even though I did not use it. From researching the tools it looks like that would all work properly, but to keep our budget low ($0) we will not be going with that method.
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