| 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 things that bothered me most, in no particular order: - Microsoft has a migration service to move email, calendars, and contacts into 365 from Workspace! Wanna find it? Good luck! It's buried (IMO) deep into the onboarding documentation. Finding it was not obvious at all. - The migration service also didn't work! I had a few years of emails and calendars in my Workspace. It would frequently error out due to API timeouts, even while transferring. While I was eventually able to get (most of?) my emails into 365, I had to import my calendar and contacts manually. (I wasn't confident that 365 got _all_ of my emails either.) - 365 and Google don't map contact fields one for one. As a result, while I had all of my contacts on my devices, their numbers were missing. Fixing this took longer than I wanted it to. - "OneDrive" for Business is a complete joke compared to Google Drive. Microsoft's offering is "here's a 30GB SharePoint installation". This was particularly troublesome for me given that my wife and I have a shared folder on Google Drive and an equivalent on OneSharePoint wasn't immediately obvious. - There are 750 billion different Admin panels! You can configure everything in your Workspace tenant from admin.google.com. On 365? You'll need to use admin.exchange for your mail, Azure (!!!) for your authentication, portal.office.com for some other stuff, etc. - 365 enables passwordless auth through Authenticator, which is a good thing, but this also disables IMAP login, which is not good. - Due to Microsoft pushing admins to use PowerShell more often several years ago, there are many configuration options that cannot be done by UI. You need to do it via PowerShell. While this isn't a problem for me (PowerShell used to be my primary language years and years ago), this is a problem when I want to make a change that took less than five minutes to do on Workspace. - In the year of Our Lord 2023, Microsoft thinks it's appropriate to give Microsoft 365 users at 50GB inbox by default. 50! GIGABYTES! - Exchange's anti-spam filtering is outrageously aggressive! This was the final straw for me. A lot of really important email would get sent to Junk (which has an auto-delete policy by default!) I had to check my Junk folder every day, something I haven't needed to do in years on Google Workspace. I'm sure there's a setting deep within admin.exchange to tune this, but it was not obvious when I looked. So while I'm not a huge fan of paying Google $12/month ($20/mo now), it's still the best solution for people like me who want more than what Gmail and Calendar can provide but not an entire enterprisey solution. |
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.