What moves across, and what doesn't
The supported path for mail, calendars and contacts is documented by Microsoft[1], and Google's own admin-level export documents what is and is not included on their side[2].
A move from Google Workspace to Microsoft 365 covers three things: your email, your calendars and contacts, and the files in Google Drive. Email, calendars and contacts travel together. Drive is a job on its own, and it helps to know that before you start so nothing catches you out halfway through.
Here is what comes across, and what needs handling separately:
What does not survive the move perfectly
Every migration vendor's own fidelity documentation says the same thing, and it is better to hear it now than in week three. BitTitan and SkyKick both publish per-object fidelity matrices for Google-to-Microsoft moves showing which attributes convert, which approximate and which are dropped[3][4]. The ones that matter for a small team:
- Gmail labels become Outlook folders. This is the big one. A Gmail message can carry five labels at once; an Outlook message lives in exactly one folder. The migration picks one and copies the message into each labelled folder, so you either lose the multi-label view or gain duplicate copies. Neither is wrong - it is a structural difference between the two systems, and no tool fixes it.
- Gmail filters and rules do not migrate. They have to be rebuilt as Outlook rules. Budget 20 minutes per heavy user.
- Google Docs, Sheets and Slides are converted, not moved. Conversion to Word/Excel/PowerPoint is good but not perfect: complex formulas, apps-script automations, add-ons and pixel-level formatting need checking. Anything running Apps Script needs rebuilding in Power Automate.
- Shared drive permissions approximate. Google's sharing model and SharePoint's do not map one-to-one. We rebuild the permission structure deliberately rather than pretending it transfers.
- Google Sites, Forms, Keep and Chat history have no destination. Export what matters before you close the account.
The reassuring part is that your mail is copied, not moved. Nothing is deleted from Google while the move is happening.
The two ways small businesses migrate
For a team of 5 to 50 people, two paths are worth weighing up.
The built-in path (Simplified Gmail Migration). Microsoft built this tool for small businesses, and it moves mail, contacts and calendars together. It handles up to 1,000 mailboxes, far more headroom than a small business will ever use. For most companies, this is the one to pick.
Email-only (IMAP migration). This copies the inbox and folders, but leaves contacts and calendars behind unless you export them yourself. It fits very small, simple setups under about 150 users where email is the only thing that matters.
Once you add a lot of shared mailboxes, aliases, or a large Drive, the move is better run as a managed project than clicked through live.
The order that keeps mail from going missing
The sequence matters more than the tool. Follow it and nothing falls through the cracks:
- 1Set up the Microsoft 365 tenant and verify your domain.
- 2Create every user and give each one a licence, so a mailbox is waiting before anything is copied into it.
- 3Run the mailbox migration in the background. Mail still arrives in Google as normal while this happens, and the team carries on unaware.
- 4Switch the MX record after hours. That is the moment new mail starts arriving in Microsoft 365, and it takes minutes.
- 5Leave the Google account running for 30 days, so everyone can confirm their mail, contacts and calendars made it across.
Where email actually gets lost
Almost every horror story traces back to one of these:
- The Google account was deleted too early, before the final sync had finished.
- The MX record was switched before the mailboxes had copied across.
- An email-only method was used, and contacts and calendars were forgotten.
- A shared mailbox or alias was missed, and a customer kept writing to it.
- Two-step verification on the Google side blocked the migration because no app password had been set.
None of these are hard to sidestep. They come down to a checklist and someone paying attention on the day.
What about your Google Drive files?
Drive sits outside the mail move. Your files go to OneDrive and SharePoint in a second migration, with its own plan for structure and permissions. Getting that plan right is what stops the files scattering all over again once they land. Our guide on where files should live in Microsoft 365 covers the destination in detail.
How long it takes, and what downtime to expect
For a team of ten, expect two to three weeks of background work and one after-hours switch at the end. Email never stops. People work in Google right up to the switch and in Outlook straight after, and on the day itself there is very little for anyone to notice.