Switching from Microsoft 365 on GoDaddy to Google Workspace is rarely straightforward. It’s not flipping a digital switch in the cloud and magic happens. On paper, it looks like a DNS change. In practice, it’s a project filled with detours. Without the right preparation, you end up with failed exports, missing mail, and frustrated users. Let me share an example from this past weekend.
Timeline: Client called on Thursday. Friday, we started the first steps. The client got ahead of the plan, and the MX records were set up too fast in Cloudflare to point to Google. Not the end of the world. Hiccup time – we reverted back to Microsoft until we had all back-ups completed and we were detangled at Microsoft. Saturday it was better to Zoom together for three hours. Here’s the rest of the story.
We started a migration for a small company that thought the process would be quick. One account looked routine, but when we tried to back it up, the export failed—four times in a row. The reason? Years of accumulated mail in Sent and Deleted folders and HUGE attachments. Once those were cleaned out, the export finally worked, but it still took seven hours for one mailbox to complete. That’s seven hours of machine time you have to factor into the project, even if no one is sitting there watching a progress bar. No, I did not bill him for this time, I had him text me when it was complete so we could continue through our checklist.
But that wasn’t the only surprise. Another issue: Microsoft had a death-grip on the domain, Outlook profiles. Some users were on classic desktop Outlook, others on the new version, and some only on the web. Add in a remote team overseas, and every environment needed its own fix. None of this shows up until you ask the right questions ahead of time.
The takeaway: email migrations fail when assumptions are made. They succeed when you slow down, ask detailed questions, and involve the client during the cutover. Here are some things to be aware of if you want to make this change. Here is a questionnaire I created. You are welcome to fill it out to get a quote form us. You can also share it with your IT professionals. You will need to be able to answer all of the questions in the form to make this transition.
Oversized Mailboxes Slow Everything Down
Mailbox exports fail when they’re bloated with unnecessary folders. Even when they succeed, large PSTs can stretch a project by hours. Cleanup is not optional.
DNS Records Decide Deliverability
If SPF, DKIM, and DMARC aren’t in place, some clients will never see your emails. Corporate mail systems reject what they can’t authenticate. DNS must be correct before you flip MX records.
People Make or Break the Cutover
Migrations are not “set it and forget it.” They require a live client, available to approve logins, reset passwords, and test. In our case, a three-hour Saturday Zoom call with the client made the difference between success and failure. He was terrific to be so patient. We worked well together and both cheered when we finally completed the transition for him.
Licenses Need to Be Untangled
Microsoft 365 bundles more than mail. Some users still need Word, Excel, or SharePoint. Dropping Exchange licenses without a plan may remove access to those tools.
Security Must Be Enforced
Moving to Google without enabling two-factor authentication leaves you just as exposed as before. If the account was hacked once, it will be tried again. 2FA must be standard.
What Separates Success from Failure
Discovery. Mailbox size, DNS configuration, user access methods, alias domains, licensing needs, and client availability all have to be mapped before you start. Migration is not a flip of a switch; it’s a process.
What looked like a quick job turned into days of cleanup, testing, and client involvement. That’s the reality of most email migrations. Success comes from knowing the pitfalls in advance, setting expectations, and guiding clients through each step. Handle cleanup, DNS, user participation, licensing, and security up front, and your migration will work the first time.