Hey everyone, our company is planning to move from Google Workspace to Microsoft 365 in the next couple of months, and I'm trying to figure out the best way to approach the actual migration tool selection. We're a mid-sized organization, a few hundred mailboxes, decent amount of shared Google Drive usage across departments, and some fairly complex calendar setups with recurring meetings and shared resources. I've read a bit about doing manual exports through Google Takeout, but from what I've gathered, that route gets messy fast once shared drives, permissions, and calendar recurrence rules are involved.

I've been looking into dedicated migration tools instead, and one that keeps coming up in my research is the DRS Softech Google Workspace to Microsoft 365 migration tool . It seems to cover the full range of what we need — emails, contacts, calendars, and Drive data — plus some reporting so we can actually verify what transferred correctly instead of just hoping for the best. Still trying to figure out if it handles shared drive permission mapping well, since that's honestly my biggest worry right now.

Before we commit to anything, I wanted to ask this group directly: what factors mattered most to you when choosing a migration tool? Did you run a pilot batch before doing the full migration? And has anyone had issues with permissions, metadata, or calendar data not translating cleanly regardless of which tool they used?

Any advice, horror stories, or things you wish you'd checked beforehand would be genuinely appreciated. Trying to avoid a migration weekend that turns into a migration month.