There is one fixable issue on boot when Sophos keeps requiring approval of Little Snitch Rules even though you approved the rules on the last boot.
From Sophos support:
Sophos uses processes called “Sophos[…].bundle” which install itself as a new user on the system (user: “_sophos”).
You can see this when you press the D key in a Little Snitch Connection Alert. This will show you the ID for the user "_sophos".
Rules in Little Snitch can have different kinds of process owners
— the current user “Me” for all processes running for the current active user
— “System” for all system processes running as “root” or other system users (those marked with a gear wheel icon)
— all users respectively “Anyone”—such rules are valid for every user on the system (system and all user processes)
To be able to setup the last-mentioned “Anyone” rules, ”Allow Global Rule Editing” has to be enabled in the “Little Snitch Preferences > Security” settings. There are also rule categories for “Global Rules” and ”System Rules” in the Little Snitch app window to give an overview for such rules.
The “_sophos” user is set up with a user identifier above 500 which is usually not used for such processes (see e.g.
https://en.wikipedia.org/wiki/User_identifier#Reserved_ranges).
This is why you cannot create a permanent rule (“Forever”) from that connection alert since it is not made by a system or active user process, but by a different user (“_sophos”) instead.
In order to access the rules for the user “_sophos”, they have to be made available to all users:
— Enable “Little Snitch Preferences > Security > Allow Global Rule Editing”.
— Open Little Snitch app as the user “_sophos” via the following Terminal command:
sudo -u _sophos /Applications/Little\ Snitch.app/Contents/MacOS/Little\ Snitch
(Open /Applications/Utilities/Terminal.app and paste the previous line into it, then hit Return and confirm. If there are error messages in the terminal, you can safely ignore them.)
— After typing your admin password, you should be able to see the Little Snitch app window with the rules for the user “_sophos”.
— Edit those rules to “Owner: Anyone” in order to make them global and set them to your needs.