A couple of side notes:? The "classic" standalone versions of Outlook are well-known for being "temperamental" and with difficult to diagnose issues.
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Outlook 2016 and 2019 both officially go out of support on Oct 14, 2025.
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Depending on whether or not you use the advanced features of Outlook (e.g. VBA scripts) this is a good time to consider transitioning to New Outlook if you don't intend to upgrade either to a later and in-support version of Microsoft Office (2021 - EOL Oct 13, 2026, or 2024 - EOL Oct 9, 2029) or M365.
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End of life for Outlook Classic in all its forms is currently slated for October 2029.
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Brian? ¡¤ ¡á? ¡¤ ???? ¡¤ ?Virginia, USA?- Windows 11 Pro, Version 24H2, Build 26100; M365 Family; Android 13 (Xiaomi HyperOS 1.0.10.0)
It is much easier to be critical than to be correct.
?????? ~ Benjamin Disraeli, 1804-1881
Brian Vogel