In another thread
https://community.ipfire.org/t/web-proxy-not-starts-itself/6443/2
you ask how to raise this to the developers.
Normally the best way is to raise a bug.
https://wiki.ipfire.org/devel/bugzilla
In this case I believe that a bug has already been raised on this topic.
https://bugzilla.ipfire.org/show_bug.cgi?id=12623
If this bug is covering your issue then please add your information to the bug. If it is not covering your issue then please raise a new bug as per the wiki link above.
Your IPFire People email address and password work on the IPFire Bugzilla to authorise your logon.
When you want to provide the log info I would suggest first getting your IPFire to have the problem, ie squid not starting at reboot and then copying the required log info. That way the required info will be near the end of the log that you provide.
I suspect the required logs will be /var/log/messages and /var/log/squid/cache.log.