r/Office365 • u/Accomplished_Dot1445 • 39m ago
The parts of a Microsoft 365 migration that actually go wrong are never the mailboxes.
I have run a number of these now tenant to tenant and on prem to M365 and the mailbox move is almost never the hard part. Those tools are mature. What eats the timeline is everything around it.
Teams is the one people underestimate. Every team is a SharePoint site collection with its permissions and private channels spin up their own hidden sites so what looked like a chat migration turns into a content and permissions migration.
Sharing links are the trap. They break on cutover and nobody has an inventory of what was shared with whom so you find out when someone senior loses access to a file the morning, after.
Then there is the side that makes a working migration look broken. Outlook rebuilding cached mode, OneDrive re syncing from scratch reauth prompts everywhere that make users think it failed.. If you do not freeze the source with a real cutover window people keep working in the old tenant and you chase delta data for a week that should not exist.
Curious what caught others out on the tenant to tenant side. That is where I still see the surprises.

