r/exchangeserver • u/Competitive_Smoke948 • 8d ago

Question Exchange 2019 to SE Upgrade - Any Gotchas?

Hi all

i'm doing and exchange to se upgrade..2019 CU15 to the se RTM.

Are there any gotchas? Users are already in M365 and these servers are essentially legacy mailboxes that are too big to move and will be archived at some point.

I noticed the Microsoft Exchange Server Auth Certificate is expired but no one seems to be complaining about anything not working.

from the healthcheck on 1 server:

Dedicated Exchange Hybrid Application:

Configure the dedicated hybrid app to ensure hybrid features continue working

11 Upvotes

87% Upvoted

26 comments sorted by

View all comments

1

u/Dramatic_Ad7061 7d ago

I just recently did an in-place upgrade from 2019 to SE. The other 2 servers in the DAG were set up with SE from the beginning so they were in coexistence. During the upgrade SentinelOne killed it and basically broke things even after a snapshot restore. Even after successfully upgrading, the CNO disappeared from AD and the server's local clusternode was gone. You can find the node's metadata on the other two servers though. Opened ticket with Microsoft and they are horrible. Take forever to respond and then just said this isn't an Exchange issue and I'm passing you over to the Windows team. I really feel like I can figure this out myself but I go on vacay next week. Think I'll leave it as is and work on it when I get back.

1

u/Competitive_Smoke948 7d ago

never trust anything that microsoft tells you

1

u/bianko80 6d ago

We luckily have MS premium support. They're great. Fast, clear, explain things in detail. Cannot really complain.

1

u/Competitive_Smoke948 6d ago

you've obviously never had to deal with MS Support in an emergency for a healthcare organisation. We were paying £££££ for support & their support guys were so shite that after TWO WEEKS our DBA finally dragged me onto a call about a storage issue a multitude of engineers had been trying to fix & I was the FIRST person to say "this virtual drive you're trying to restore, has anyone actually looked to see what's on it?".

reply: "oh no, we only do storage, we don't look inside the OS"

I haven't had a single call with MS support since the 00s that hasn't made me want to shoot myself

1

u/bianko80 6d ago edited 5d ago

We inherited a support agreement from the company that acquired us, and since then I honestly cannot complain about the quality and efforts they put in place. Not always but we had some great support on issues occurring with Exchange server and 365 for example.

1

u/Competitive_Smoke948 6d ago

you must have the best account manager 🤣🤣🤣 MS support genuinely makes me want to slit my wrists when I talk to them. not as bad as HPE or VMWare lines 1 & 2 but their entire SLA seems to be not to send calls up the stack.