Hi Bryce,

Thank you for the prompt response.
I wasn't able to reproduce the crashes with a script yet, however, I have been 
able to isolate the issue a bit more.
It seems like it only happens when ssl-bump is used - I'm using the newly 
introduced squid-openssl package.
I've attached a config file which is based on the following entry in Squid's 
FAQ and didn't cause the same crashes in squid 4.x (compiled with openssl): 

Using this config requires the squid-openssl package and the below commands 
must be executed before starting the service, otherwise squid gets stuck in a 
crash loop:
/usr/lib/squid/security_file_certgen -c -s /var/spool/squid/ssl_db -M 4MB && 
chown -R proxy:proxy /var/spool/squid/ssl_db

If I set the proxy config on my Windows laptop to point at the squid proxy 
running with the attached config on Ubuntu 22.04, squid crashes and restarts as 
soon as I try to open Outlook or Word. I cannot reproduce this issue with a 
config where ssl-bump is not used, even when using the squid-openssl package.
I tried using a Python script to simultaneously call some of the https URLs 
that I found in the logs, but squid didn't crash that way.
I'll try reproducing it using an app on an Ubuntu desktop VM and keep trying 
with the script as well.

** Attachment added: "sample squid config"

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  FATAL FwdState::noteDestinationsEnd exception: opening()

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