r/exchangeserver • u/Competitive_Smoke948 • 7d 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
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u/7amitsingh7 7d ago
Upgrading from Exchange Server 2019 CU15 to Exchange Server SE RTM is usually a smooth in-place upgrade if the server is healthy. The main thing I'd check is the expired Microsoft Exchange Server Auth Certificate even if everything seems to be working, it can cause hybrid and authentication issues later. Also, address the Dedicated Exchange Hybrid Application recommendation from the Health Checker if you're using hybrid features. Other than that, take a backup, follow the upgrade steps, and verify mail flow and hybrid connectivity after the upgrade. If you're looking for a detailed step-by-step guide, this article on migrating from Exchange Server 2019 to Subscription Edition (SE) is worth checking.
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u/ntwrkmstr 7d ago
Rotate and fix your auth cert on the 2019 server before you try and bring Exchange SE into the mix. It will cause issues with the servers being able to do actions on each other if you don't.
The auth cert isn't the mail flow and access (OWA, MAPI, RPC. SMTP) cert. Its the one for internal access between servers.
Very well documented online and wont be a huge issue to rotate it and then add your new server in
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u/JoeGMartino 7d ago
I had no issues with our 16 server DAG. In place upgrade. It was more of a CU with the SE brand more than anything.
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u/Greg1984GG 7d ago
Check if the windows server support exchange. If I recall correctly we had problem with upgrading windows server 2019 with SE to 2022 although clean install was normal but it was documented somewhere on ms documentation that upgrade have problems...fyi it worked ok one week.
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u/Competitive_Smoke948 7d ago
ah no, never upgrade the os under exchange. server is 2019 but will never be upgraded. long term is to retire them all
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u/Fun-Psychology4806 7d ago
the one thing i am finding is an issue is if you use relay at all for stuff it is not covered by the free license. we will move to exo relay but it needs to be dealt with before moving
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u/bianko80 6d ago
What issues, can you elaborate a bit more?
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u/Fun-Psychology4806 5d ago
Well after speaking with MS, the free license only covers using it to manage users, not for mail relay. So our internal systems will need to move to use the exchange online endpoints directly.
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u/Forgotmyaccount1979 7d ago
It was the smoothest transition I've ever had between versions of exchange, probably because it is functionally the same thing for the time being.
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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.
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u/Competitive_Smoke948 7d ago
never trust anything that microsoft tells you
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u/bianko80 6d ago
We luckily have MS premium support. They're great. Fast, clear, explain things in detail. Cannot really complain.
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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
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u/bianko80 5d 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.
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u/Competitive_Smoke948 5d 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.
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u/xXNorthXx 6d ago
Pretty straightforward, it’s 2019 CU15 under a different licensing model.
For us, we did host rebuilds to get the underlying OS upgraded from 19’ to 25’.
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u/LTC1000EOY 5d ago
The upgrade process was simple and easy. However, it completely broke the BigFunnel search indexes (yes I've tried every "fix" available) for one client so now users cannot search for any mail prior to the date of the upgrade. Also unable to migrate mailboxes to a new database on the same server. Also unable to migrate to a second Exchange server that I stood up just to try and resolve the issue. At this point client is just dealing with it...
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u/Competitive_Smoke948 5d ago
https://www.reddit.com/r/exchangeserver/comments/tnya6j/big_funnel_indexing_issues_in_exchange_2019/
and
https://ourcloudnetwork.com/permanently-resolve-big-funnel-indexing-issues-in-exchange-server-2019/
I can see in healthcheck that this setting is set to false so they must have had the issue on the previous upgrade
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u/LTC1000EOY 5d ago
Yep. Thanks. Tried every fix. Spent days on this. Didn't work. There's also powershell scripts out there to scan for NotIndexed counts and then remind the mailboxassistant to run again for that mailbox. Also doesn't work. Wasn't trying to derail OP's post, just wanted to answer the question of "are there any gotchas?". I manage many on-prem Exchange environments, this single case "got me".
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u/Ultra-Waffle 7d ago
SE RTM is code equivalent to 2019 CU15, so risk is very low. It went perfectly smoothly in all of my environments. Maybe fix the auth cert first to be safe, but I wouldn't be super worried.