How I Restored My Email Messages to the Hotmail Servers

OK! It’s My FAULT! First of all, I need to state that my email messages did NOT disappear as I was proclaiming on twitter (not that it would matter, since no one @Hotmail, nor @Microsoft came to my rescue.) Regardless, after some soul searching, and back-tracking, I have determined that I am the reason that my messages were removed from the Hotmail servers. To be more correct, my using Apple’s OS X Mail application’s default setup for a Hotmail account is what resulted in the removal of all my old messages from the Hotmail servers. Obviously, I should have reviewed Apple’s default settings for my email account before I allowed it to go live.  The following post will explain how Apple’s Mail application setup my Hotmail account, and then what I needed to do to get my messages back onto the Hotmail servers.

Couple of things: I have a Windows computer too. My Mac is running Lion with Mail 5.3. Do not delete your messages; Always copy and never move messages (the only exception would be in considering how I would do it differently as a commented that the end of this post.)

How Apple’s OS X Mail Application Configures a Hotmail Account by Default

By default, when you setup an email account in your Macintosh Mail you are first greeted by a configuration dialog box.

Apple, always trying to make things easier for the user, starts the dialog asking for the bare minimum of information about your email account (i.e., your name, your email address, and the password to your account.) If Mail is familiar with your email server, then it will automatically add the incoming/outgoing server addresses, as well as, whatever security settings are needed. This is a very convenient way to get your web-mail accounts (e.g.,,,, etc.) configured into Macintosh Mail, because you do not need to track down  the manual settings; Mail already knows Them.

Hotmail is different. The free Hotmail account that most people have doesn’t support the IMAP protocol, so Macintosh Mail sets it up as a POP3 server (which is available with the free account.) This is great! Mail knows the server addresses and the security so you don’t have to. However, Mail also configures this account with options to delete all messages a week old.  After completing the setup for your Hotmail account go look at the configurations. Under the “Advanced” tab you’ll find the default settings are to “Remove copy from server after retrieving a message: After one week.”

<PERSONAL RANT> “Since, Hotmail is a web-mail service,  it doesn’t make sense to remove the email message by default. It’s fine if a user’s personal choice is to not leave mail on the server, but it seems counter-intuitive to delete the server side messages by default. It’s HOTMAIL! Though this is a pretty common default setting for a POP3 email client, it’s made confusing because Macintosh Mail is “Helping” to setup HOTMAIL!”</PERSONAL RANT>

If you’re like me and want the flexibility of using a web browser for your Hotmail, as well as have access to Hotmail from Macintosh mail, then remove the check mark “Remove copy from server after retrieving a message.” That will leave the mail on the Hotmail server, while allowing Mail to download copies using the POP3 protocol.


 How I Restored my Email Messages to the Hotmail Servers

Before I begin, if it isn’t obvious yet, you cannot do this if you don’t have your messages stored somewhere. In my case, I had downloaded all the messages to Apple’s Mail application in OS X. That means that I had my email messages on my Macintosh computer in Mail, and needed a way to get them back to the Hotmail Servers (if only for my own sanity and peace of mind.) Here is the process I went through.

1st – configured my gmail account as IMAP access in Macintosh Mail.
I also have a gmail account, and I configured it in the Macintosh Mail application using the automatic default configurations. Gmail supports the IMAP email protocol (more info on IMAP here -> Basically, IMAP lets you synchronize folders of email messages.

2nd – created a new folder in gmail and copied email messages.
I created a new folder in the gmail folder structure called “Hotmail Backup” and copied all the Hotmail messages I had from the local Mail folder. Since, I have a few thousand messages with attachments, this took a while.

3rd – setup Microsoft Outlook for both my gmail and Hotmail accounts on a windows computer
So…I can’t help you if you don’t have access to a email client with IMAP type support and access to Hotmail. Microsoft only makes this available for the free Hotmail accounts using their software. That means Windows+Outlook (or maybe Live mail.) I used MS Outlook 2003 with the Microsoft Office Outlook connector installed. The Outlook Connector gives you access to your Hotmail account as though it’s a IMAP server (I believe that the Microsoft Live Mail application will do the same thing.) I setup both my gmail account (as IMAP,) and my Hotmail account (using Microsoft Office Outlook Connecter) in Microsoft Outlook 2003.

4th – Copy all email message from the gmail “Hotmail Backup” folder to my Hotmail inbox
enough said? I just selected all the message from the my gmail folder labeled “Hotmail Backup” and copied them to the Hotmail inbox in Microsoft Outlook. Since, I have a few thousand emails with attachments, this took awhile.

This worked great except for one problem. Every message duplicated in Macintosh mail on the next download of email from the Hotmail account. Since, I have a few thousand messages with attachments, this took a while.

Crap! and now I have that cleanup to do in my Mail inbox…If I was to do this again, after having copied them into the gmail “Hotmail Backup” folder, I would empty the local Hotmail inbox on my Macintosh by moving all the message to a new local folder (keeping a backup of all the messages.) That way it would be empty and ready to download all of the messages again and wouldn’t create duplicates in the inbox. However, it’d probably take a while….I have a lot of mail.



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