Switching from Outlook 2013 to Microsoft 365 outlook – confusing

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So I’ve done a lot of googling on this but no one seems to be answering these specific questions.

I have email on my domain hosting myemail@mydomain.com

I currently get and send my email in outlook 2013 via pop3/smtp from my domain hosting mailserver.

We have purchased new laptops so this seems like the right time to try jumping forward 9 years and switch to outlook 365.

Among other things I would like my email to be in the microsoft cloud, and not have to worry about a hard disk failure, and losing weeks of email when I revert to a backup pst file. Also because our current setup is a shared mailserver, too much of our email ends up in the recipient’s spam folder.

I understand from researching that I can safely(?) import the pst file from outlook 2013 into outlook 365.

I’m pretty sure that will cause it to load our several GB of email and calendar history into the “microsoft 365 cloud”?

Then do I set up the email account settings in outlook 365 to get and send email through my hosting (www.mydomain.com) email server (via imap/smtp)?

Or do I change the mail dns settings on the my hosting’s server to use microsoft 365?
https://docs.microsoft.com/en-us/microsoft-365/admin/get-help-with-domains/create-dns-records-at-any-dns-hosting-provider?view=o365-worldwide

Any experienced insight you might have on this will help me feel more confident before I pull the trigger on switching.

Thank you!

Kallen Web Design

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I would use Microsoft to host the email. Follow the documentation. You can do it all at once if the volume is not too much or migrate a few mailboxes at a time. Once it is all in the cloud you can decommission or repurpose the email server. we did this but it has been a long time so I don’t remember the exact steps. We followed Microsoft’s instructions and it worked out well. If you are unsure contact a local Microsoft partner to help. It may cost you a bit but would be worth it to avoid problems along the way.

--Joe

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KWD

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Thanks. These are just two personal stand-alone email boxes, no exchange, and the server is the hosting company’s shared mail server.

Kallen Web Design

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