Hi @Cory Fiala
Did you encounter any search problem? Below thread seems discussed the similar error like yours: Exchange 2016 CU16 + Outlook 2016/2019
And I checked the discussion in this thread, it shared a reference link about this question: Outlook 2016/2019 Search Workaround
We had an issue where people searching in Outlook 2019 would get a "Something went wrong and your search couldn't be completed. It looks like there's a problem with your network connection." error. All network tests through Outlook succeeded, all updates installed, we recreated Outlook profiles, disabled cached Exchange mode, and reinstalled Office. Nothing worked. I came across a TechNet thread that suggested a registry fix, and that worked great.
HKEY_CURRENT_USER\Software\Policies\Microsoft\Office\16.0\Outlook\Search
Value name: DisableServerAssistedSearch
Value type: REG_DWORD
Value: 1
EDIT: I also recommend using GPO to force Cached Exchange Mode to download all items because Outlook won't be able to ask Exchange to search for non-cached emails.
User Configuration > Policies > Administrative Templates > Microsoft Outlook 2016 > Account Settings > Exchange > Cached Exchange Mode
Enable:
Cached Exchange Mode (File | Cached Exchange Mode) – Select Cached Exchange Mode for new profiles: Download Full Items
Cached Exchange Mode Sync Settings – Select Cached Exchange Mode sync settings for profiles: All
Use Cached Exchange mode for new and existing Outlook profiles
EDIT 2: There's a known bug where setting "Select Cached Exchange Mode sync settings for profiles" to "one week", "two weeks", or "all" causes the setting to be displayed incorrectly. When you reopen GPMC and have the policy set with one of the above options, it will show as "three days." This is only a visual bug, and the policy is still applied correctly. You can read more on that here:
EDIT 3: Changed title to include Outlook 2016, since it shares the same base code with 2019 and also has this problem.
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