I have 2 clients that are both currently on SBS2011 (Server 2008R2 and Exchange 2010). What is the preferred method to migrate to O365 Hosted Exchange? In the past I have always just exported PST files and the recreated email accounts online and then imported the PSTs. This method seems to work alright with the exception of cached autofill accounts that we usually just clear from Outlook. I was looking at the option of using Azure AD Sync and then moving the mailboxes but seems like more effort than what is needed. The file shares are being moved to Sharepoint/OneDrive and the server is going away. Anyways, what is your typical migration plan? The clients have about 15 accounts a piece.
Don't even make the PST.
Just create a remote migration sever in O365 and suck the data up.
I just did it for 139 mailboxes.
The two clients are both on different networks with their own SBS servers. Can I use Azure AD connect to migrate both servers users to the same O365 account? We basically want to merge the two environments into one online account. There are not duplicate usernames on the two servers so I don't think this will be a problem but just curious if you've ever had to do something like that.
AzureAD has nothing to do with the migration of email. You are mixing things.
If you are wanting to switch to Azure AD and have disparate environments, then you need to just import the email as I mentioned. Then have everyone sign in to O365 and update their passwords, then disjoin the local computers form AD and rejoin AzureAD.
I would completely skip the disaster of merging two unrelated, on-premises, AD forests.
So which tool or method do you use to migrate the mailbox? Powershell? Everything I have seen/read shows that you first create your users with the connect tool and then move the mailboxes.
I did this in O365 itself. You download their excel template, fill out the information, then run through the O365 module for importing the data and go...
In my case I was coming from SMTP, not Exchange, so I had to create all the users on O365 first, you might have to do the same.