Redirect Loop htaccess on MacOS Server

Indeed, it explains why it is so different.

Looking at the documentation of CakePHP, they mention mac OSX as following :

On Mac OSX, another solution is to use the tool virtualhostx to make a Virtual Host to point to your folder.
see : URL Rewriting - 2.x

It lets me think that it should work almost out of the box (“On Mac OSX, another solution”). Maybe we are missing something in your configuration. I can see the FollowSymLinks options and other conf everywhere except in your conf. Maybe it worst it to test the following :

<Directory "/Library/Server/Web/Data/Sites/passbolt.monigle.com">
    Options All -Indexes +ExecCGI +Includes +MultiViews +FollowSymLinks
    AllowOverride All
    Require all granted
    ....
</Directory>

That is an interesting use case, I’ll give it a try the next week on my machine.
Cheers