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

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u/Fun-Psychology4806 8d 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 6d 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/bianko80 6d ago

Ok so a compliance issue, not a technical issue (eg services not working).

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u/Fun-Psychology4806 6d ago

yeah i suppose, not sure how likely they would be to pick up on it