I tried moving away from Workspace to Offi^H^H^HMicrosoft 365 last month. I chose 365 since my wife primarily uses a Surface and Microsoft products, which would make it easy for us to collaborate. It looks like an excellent solution for SMBs or larger who have a dedicated admin that can tend to it. For a nobody like me, it was a hot goddamned mess. Death by a few big cuts and thousands of small ones. These are the th…
Migrating mail into MS365 is a terrible experience. I've set up over 30 tenants and migrated mail for them and there's no good tooling. Both the Microsoft options and all the 3rd party options I've tried do an extremely poor job or error handling and reconciliation.
Microsoft's IMAP sync is so bad at reconciliation that IMO it's reasonable to call the data integrity rating a lie. I've dealt with some really small mailboxes where you could almost grok the data just by skimming it and the (number of message) counts for imported mail were flat out wrong.
With the amount of money they charge per user per month you'd think there would be some incentive to create migration tooling that isn't hot trash, but maybe that's just me.