There are a bunch of different ways to migrate stuff but I think for the purposes of this migration there are two I want to focus on:

  • Uploading PST

  • IMAP migration

Uploading the PST is pretty straight forward conceptually – you just upload the mailbox calendar etc. An IMAP migration synchronizes the old mailbox with the new one. Once Exchange Online has all the messages I think you can use either mailbox and then you just go ahead and switch the old one off at your leisure.

What I’m Thinkin' Rn

Mailboxes/Calendar/Contacts

Ruben uses the cloud mailbox exclusively. His mailbox is less than 10GB. I can just do an IMAP sync. Should be easy. I should also teach him how to archive stuff.

Pia is more difficult since she has way more data. My proposed solution is uploading all her archives via PST+azcopy, uploading her contacts separately, then using IMAP sync for her main folder. At that point she can basically just use her old server until everything’s uploaded. The final pièce de résistance is uploading her calendar and having her not use it until it’s all up.

The rest of the mailboxes can do an IMAP sync if they want to keep them. If they want to get rid of them we can download everything as a PST and sort through it. Everything that’s kept maybe goes into a folder in the archive.

By the way I can start this process whenever with the [email protected] email addresses. The gallegoslaw stuff is just an alias.

DNS

I think I can change the ownership of the DNS name to Cloudflare without messing up the MX records thus not messing up the routing. I need to like quadruple check this.

So, switch domain ownership to cloudflare, wait for that to complete, then make sure it works well. When I’m ready to make the switch use the Microsoft DomainConnect or whatever to quickly switch the MX records over and BOOM. Done.

Users

Now if changing a TXT record is all I have to do before I have the option of adding users under that domain in Microsoft then this is quick. Before transferring the domain to cloudflare I import it into Microsoft. At that point – and during the transfer process to Cloudflare – I can start adding users under the gallegoslaw domain.

If I have to wait until Cloudflare has it, no biggy, I can honestly wait until the last second to add the gallegoslaw aliases because they are just aliases.

Questions/Considerations

  • When uploading the PST I can probably upload the archived messages to the archive but I might have to separate out the calendar and contacts and upload those separately.
  • When doing an IMAP migration can I use either mailbox?
  • Make damn sure and test that I can switch DNS to cloudflare without fucking anything up.
  • When during the Microsoft import domain process can I start adding users under that domain name?