Outlook 2003 to Windows Live Mail Using Hotmail – Should Not Have Been This Difficult

Setting up a new Windows 7 machine, the challenge is to get the email from the old computer to the new.  SHOULD  have been easy since the email provider is Hotmail and using Outlook 2003 with Outlook Connector on an Windows XP machine.   In theory the email is stored in Hotmail so one would think that all I needed to do was add the Hotmail account to Windows Live Mail on the Windows 7 machine.

I discovered that some email was being stored locally.  Not a big deal, just drag the local folders to Hotmail thus now storing all email in Hotmail.  This is when the fun begins….

In Outlook 2003 I can see all the folders that one would expect to be in Hotmail.  I configure the Hotmail account on the Windows 7 Machine.  But, all of the messages are not showing up.  All folders are there but some folders contain no message.

I logon to Hotmail, via a web browser, and verify that the folders in question are indeed there and that the folders have no messages.  This leads me to believe that the Outlook 2003 machine did not finish syncing the messages to Hotmail.  Problem is, don’t know why they are not synching.

Instead of wasting time figuring out why the messages would not sync with Hotmail I decided to just export the Outlook mailbox to a PST file.  I was feeling pretty smart at this point..but…you cannot import a PST file into Windows Live Mail!

I then did a Google Search….one suggestion was to install a trial of Outlook on the Windows 7 machine and import the PST.   Then start up Windows Live Mail and tell it to import from Outlook…yea that didn’t work.  No option in Windows Live Mail to import from Outlook.

Another search result suggested to import form Outlook 2003 into Outlook Express.  What the heck I thought, couldn’t hurt to try this.  Well this worked, I was able to import the folders that had the missing email messages!  Great, now to get the Outlook Express folders/messages into Windows Live Mail.

This step, bringing the messages from Outlook Express 6 to Windows Live Mail, was pretty simple.  Just copied the Outlook Express folder from the XP machine to the Windows 7 machine and did an import with Windows Live Mail.

After the import the missing folders appeared under the “Storage” folder in Windows Live Mail.  I decided to drag the messages from inside these folders to their “empty” folders in Hotmail.  This seemed to work ok.  Until, Windows Live Mail tells me that it cannot send or receive email.

I did see an error message and I did a search on the message id, the resolution is  “check your internet connection”.

This gave me a little chuckle since I was connected to the Windows 7 machine via Team Viewer, over the internet….

Since I had a copy of the messages I opted to removed the Hotmail account from Windows Live Mail, and then add it back.  This corrected the issue of not being able to send or receive email from within Windows Live Mail.

I then started to copy the email messages again.  After each copy I would perform a send and receive.  First few folders worked fine.  Then I copied 24 messages from the local folder to the Hotmail folder.  After doing this, Windows Live Mail started to show the same error message about not being able to send and/or receive email.

At this point I decided that it’s best to just keep the missing email messages in the local Storage group as it appears Windows Live Mail and/or Hotmail has an issue with copying email messages in bulk.

Again, this should not have been this difficult.