I'm struggling with this combination of an RDS farm with UPD disks, Office 365 for email, and Outlook 2016 on the RDS. The dilemma is if my users have cached mode turned on for their Office 365 mailbox, search breaks. From what I've read, this is because of the non persistent nature of search indexing in an RDS. Also, I'm only caching 3 months to conserve space. If the user complains about this, we can turn cached mode off. However, with this setup, attaching documents can cause Outlook to lock up due to latency issues. Search works, though!
I haven't seen any solutions to this besides turning to a third party vendor. With all of these things being Microsoft solutions, you would think there would be some sort of support solution.
@Tyler DoWe are in the exact same boat. The Windows Search Index on the RDS host deletes the user's index for cached Outlook when they log off, and non-cached Outlook can be problematic, as you stated. It would be nice if Microsft kept the Outlook index in the user's profile, but I guess that would make too much sense. Please let me know if you hear of any other solutions.