I have the same, on Microsoft® Outlook® 2019 MSO (Version 2311 Build 16.0.17029.20028) 64-bit .
Tried safe mode, still outlook crashes when sending mail.
Tried repairing OST file, outlook still crashes when sending mail.
I have one Microsoft Exchange account which crashes when sending, and one pop3 account which works fine in the same outlook client.
From the application log in the event viewe:
Faulting application name: OUTLOOK.EXE, version: 16.0.17029.20028, time stamp: 0x654b6bcf
Faulting module name: OUTLOOK.EXE, version: 16.0.17029.20028, time stamp: 0x654b6bcf
Exception code: 0xc0000005
Fault offset: 0x000000000115f1c0
Faulting process ID: 0x2b38
Faulting application start time: 0x01da1eae756d4082
Faulting application path: C:\Program Files\Microsoft Office\root\Office16\OUTLOOK.EXE
Faulting module path: C:\Program Files\Microsoft Office\root\Office16\OUTLOOK.EXE
Report ID: db3295a2-3b76-49f7-b2d9-8e4948acd72b
Faulting package full name:
Faulting package-relative application ID:
Please advise.