I can’t be sure of anything at this point other than I have had Outlook 2019 crash on me a number of times and it seems to be related to having a Keyman Keyboard selected. I’ve written a keyboard for one of the local first nations and sometimes when I have it selected and I’m writing an email Outlook crashes with an exception. It happens fairly infrequently and so far I’ve only seen problems with Outlook. When I use the regular English (Canada) keyboard I don’t have a problem. Restarting Outlook doesn’t seem to clear the problem. Once it starts happening it keeps happening until I select a different keyboard and then restart Outlook.
So my question at this point is what information should I collect when it happens that would help in debugging the problem since I can’t reliable reproduce the problem yet?