I realize there is at least 3 different ways to put someone on legal hold. The first is right on the Active Users page under the mail settings (as long as they still have a mailbox). The second is on the security & compliance admin center under e-discovery. The third is powershell.
My question is- why is it when you enable legal hold on any one of these places for a user, when you get any of the other spots, it doesn't ALSO say enabled?? Even checking powershell, if you've turned it on in either of the 2 spots i mentioned, it shows enabled: false...
I know in Microsoft there is many ways to accomplish the same task, but usually the status matches afterwards. Why not in O365?
There are actually different flavours of hold. More specifically, the one you configure from the SCC is not litigation/legal hold, thus it will not be directly reflected on the corresponding mailbox property. Instead, you will see it listed as entry under the InPlaceHolds property. And I'm still making some assumptions on the way you configured that hold, as it can also be company-wide, in which case it might not even be "visible" in the mailbox properties.
TL;DR, the status should match, excluding some synchronization issues. But it's important to keep track of what type of hold you have enabled.