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We did an Exchange 2013 CU21 > 2019 CU1 migration. Basic setups. Just Mailbox roles. No DAGs.

All arbitration, public & user mailboxes transferred successfully, and Exchange 2013 decommissioned/uninstalled.

Exchange 2019 has a different internal name, but same external name.

Internal & external DNS / autodiscovery updated, and clients find the new server and connect to their mailboxes without issue.

OWA works flawlessly, including searching. So I know the Exchange Fast Search service / subsystem is working correctly.

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However, searching from many Outlook clients fails when using server-side searches. Outlook will spin for a while, and then error with "It looks like there's a problem with your network connection."

Clicking on "Let's look on your computer instead" to use a client-side search works fine from that point.

I've tried rebuilding the Windows Search Index on a couple computers, and that didn't fix it. I can use GPO / registry to force client-side only, but it'd be much better to find the cause of this and get server-side searching working between Outlook & Exchange 2019.

Any ideas?

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You say this is Outlook 2019, but is it MSI based (Retail/OEM/VL) or Click-To-Run based (Office 365)?

If Click-to-Run based then there is an update (or two) released in the last couple of weeks that may resolve this. In order to get the updates you'll need to change the Office 365 update channel to the Monthly Channel and then force an update, both of which can be accomplished with the following commands on each computer:

“C:\Program Files\Common Files\Microsoft Shared\ClickToRun\OfficeC2RClient.exe” /changesetting Channel=Current

“C:\Program Files\Common Files\Microsoft Shared\ClickToRun\OfficeC2RClient.exe” /update user
  • Not specifically Outlook 2019... Exchange 2019. All supported versions of Outlook (2013, 2016, 2019) on random computers. – ltwally May 30 at 5:58

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