Switch from Hotmail to Outlook and Easily Change Accounts

Do you want to switch from Hotmail to Outlook? I made a change recently. Here is how you could do it, too.

There are a few ways to get this done. You can perform a full data transfer using the export/import method, a live transfer using the desktop client, or an alternative method with EML files.

However, if you are thinking about forwarding all emails. STOP. If changing from Hotmail to Outlook had been as simple as hitting the forward button, we would not have been here. Let me explain why forwarding is a bad idea.

Don’t Forward Mails to Switch from Hotmail to Outlook

I get why you’d want to. It seems like the easiest fix. But I’ve been down this road, and it’s a trap. It breaks email in more than a few ways. See below.

It makes replying difficult. When you forward a message, your new Outlook account thinks the email came from your Hotmail address. So when you hit “Reply,” you’re just talking to yourself. It makes having a conversation impossible without manually copying and pasting addresses every single time.

Your emails become Spam. Mail servers hate forwarded mail. When your new inbox sees a message that claims to be from your bank but was sent by Hotmail, it flags it as suspicious. In the best case, it gets buried in your Junk folder. In the worst case, it gets blocked completely, and you’ll never even know you missed it.

It creates a mess. Everything gets “Fwd:” tacked onto the subject line, and the body is cluttered with —- Forwarded message —- text. It looks unprofessional and makes searching for anything a total nightmare.

That’s why we have to bother with the rules. The “Redirect to” option is the proper way to do it. It sends the original, clean email so you can reply to it and trust that it will arrive safely. We will get back to this method later. First, let us see some transfer techniques.

The Full Data Transfer (Using a .PST File)

This process involves exporting all your Hotmail data into a single .PST file and importing it into your new Outlook account.

Part 1: Exporting Hotmail and Importing the Data in Outlook

• Login to your Hotmail account via the Outlook web portal.
• Open settings (Cog icon at the top right corner).
• Go to General > Privacy and Data > Export Mailbox.

Now, all you have to do is wait. Depending on the amount of data in your Hotmail account, it may take up to 4 days for the data to exit your account (Although practically, in my testing, it was less than that). Soon, you’ll get a new email indicating a successful export. Download the Hotmail email conversations from there and proceed to the test phase of the transition.

Part 2: Add .PST File and Switch from Hotmail to Outlook

Now you’ll see that in the mailbox export, what you get is, in fact, a PST File.

Users may assume they can log out of Hotmail and back in, this time to their Outlook account and Import.

Outlook Web does have an import mechanism, but it is only for .eml files. Don’t make the mistake of manually changing the file extension to trick an import. It won’t work and may corrupt your data. Here is what you should do to switch from Hotmail to Outlook:

• Install/Update the new Outlook app.
• Have a copy of classic Outlook running in the background.
• Add your Outlook account (that has an active M365 subscription) to the client. (Settings > Accounts > Add account > Follow on-screen instructions)
• Once your Outlook account is ready, open Settings again.
• This time, go to Files > Outlook Data Files > + Add file
• Browse for your exported Hotmail data and Follow the on-screen prompts to add it to the Outlook account.

However, you may encounter some problems.

Moving Hotmail to Outlook: New Client Issues

These steps sound simple to implement but have hidden drawbacks.

One such major issue is that the + Add file button is sometimes greyed out/disabled.

In my case, it happened even when I had an M365 business subscription account + classic client in the background.

If you encounter the same problem, do what I did. Use the classic client.

The new Outlook has very recently started supporting PST files, and it does so in a very limited manner. The contacts, as well as the calendar, are not supported + there are so many different conditions like:

• Premium license requirement
• PST file must be originated in a Microsoft account,
• Classic client running in the background, etc.

Making it a confusing and complex process. If you choose a purely Classic client route, there are fewer restrictions. That is why it is still the better client of the two when we compare both on a feature-by-feature basis.

Switch from Hotmail to Outlook via Classic Client (Recommended)

Here is how you import similar Hotmail data into an Outlook account setup in the classic edition.

• Go to File.
• Open & Export > Import/Export.
• This opens the Import Export Wizard to stay on the default Import from another program or File > Next.
• Switch to Outlook Data File (.pst) > Next from the default CSV position.
• Browse for the Hotmail file, choose any one import option > Next.
• The last screen of the Import Export Wizard is where you select the Outlook account as the intended location and hit Finish.

Wait and let the classic client do its job. Cloud sync of M365 ensures that the changes made in the classic client are reflected on your account everywhere else. So you should soon see the data on the web, mobile, and new Outlook client if you have set up your account there.

The Live Transfer (Using any Outlook Client)

If you want to go one step further and do a real transfer, then both the classic and new Outlook for desktops allow you to drag and drop emails from one account to another.

Set up both Hotmail and Outlook for the client. Doing this is enough for you to have simultaneous access to both accounts. You can do this in classic, new, and even mobile. Use this feature to switch from Hotmail to Outlook.

In the mobile app, you can trigger all the main views. This will show you all the emails from all accounts in a single inbox. You can always turn it off if the screen gets too cluttered.

Second Manual File Transfer (Using .EML Files)

PST is not the only file format that can be added to the Outlook account via the client. The new Outlook has an all-new bulk .eml import as well.

• Make a blank folder on your desktop called “Hotmail data in EML.”
• Then, download all messages from your Hotmail account. You won’t be able to download all messages at once, only one at a time. This switch from Hotmail to Outlook is slow but allows you to perform message-level filtering, which is impossible in the PST mailbox export, which is an all-or-nothing export type.
• Open the new Outlook client once you have the complete EML collection in the desktop folder. Ensure that the destination account is set up.
• Go to Settings > Files > Import > Start Import.
• Browse and select the parent EML folder.
• Choose an existing folder or make a new one to add this data.
• Click Import.

Note that this is not a true transfer, as your Hotmail account retains the original copy of messages. It is just that now those messages also exist in your Outlook account.

What to Do to Complete the Switch from Hotmail.com to Outlook.com

We have moved the existing email data from Hotmail to Outlook. However, our tasks don’t end there. We need to ensure the new Outlook account replaces Hotmail fully. For that, you need to do the following:

Handling New Incoming Emails Correctly

• Start email forwarding in Hotmail so all new emails are automatically redirected to Outlook.
• Settings > Mail > Forwarding and IMAP.
• Enable Forwarding and add your Outlook account under the “Forward my email to:” bar.
• Use an external account like Gmail to test whether this forwarding is working correctly.

Send an Update mail to all your contacts informing them about the change so that you reduce the incoming emails on the old Hotmail account. Instead of adding every email one by one in the to/cc/bcc line, make an Office 365 group, add all your contacts, and send a mail.

Set Automatic replies for everyone else that still tries to contact you on the now defunct Hotmail.

• Settings > Account > Automatic replies > Turn on automatic replies.
• Draft a message and Save.

Switch from Hotmail to Outlook Using this Alternative to Auto forwarding

Unfortunately, this process does not work as we intended but works the way Microsoft intended. Let me explain.

Outlook (the email client service, not your account) treats Forwarding as the full and final request and redirects your mail to the destination account. So the automated reply you set up never gets triggered and your would-be sender keeps sending all mails to the Hotmail account. Your emails would still reach the Outlook account but when you try to reply the sender’s spam filter may prevent delivery, making back-and-forth communication difficult.

Instead, what you can do is set up a rule that redirects messages while allowing an automatic reply.

• • Go to Settings  > View all Outlook settings.
  • Go to Mail > Rules.
  • Click + Add new rule.
  • Name your rule: Something clear like “Redirect All”.
  • Add a condition: For the condition, select “Apply to all messages”.

• Add an action:

• • Choose “Redirect to”.
  • Enter your new Outlook email address.
• Save and run the rule to apply them to existing messages.

Conclusion

in this blog, we saw how many different ways to switch from Hotmail to Outlook exist.  From export-import to email drag and drop, downloading emails one by one, accumulating and uploading them to the use of rules. However, none of the solutions match the ability of simultaneous multi-account transfer in the automated tool used for easy transfer.