What’s the biggest headache your company faced during a Google Workspace or Microsoft 365 migration?

For us, the biggest headache wasn’t actually moving the mailboxes — it was everything around them.

DNS/MX changes, SPF/DKIM/DMARC, old POP/IMAP accounts, missing emails, calendar migrations, and users having different setups made the process messy. The tricky part was making sure there was no disruption while switching everyone over.

The lesson for me was: migration planning and validation matter more than the actual data transfer. A test migration with a few users first saved us from some nasty surprises later.