Defense+ VS Cygwin in stricter setup

As you may or may not know, Cygwin is more or less Linux command line tools for Windows.

It launches a file called Cygwin.bat which will launch bash.exe which in turn will launch many other process in order to create a functional shell.

In a normal setup everything will work normally as long as you let Cygwin run inside the Sandbox. If you wish it to run outside the Sandbox, setting Cygwin.bat as a “Trusted File” and on Computer Security Policy as type “Installer or Updater” will make Cygwin work flawlessly (outside the Sandbox).

However, I’m trying to disable the automatic detection of Installers.

Rationale: when trying to install a software which uses for example “config.exe” as its installer, I’d start config.exe, mark it as an installer, quit it without installing anything and then restart it. This time it’d be marked as an installer and supposedly all would work fine.

So I thought I’d disable “Automatically detect the installers / updaters and run them outside the Sandbox” and enable “Automatically trust the files from the trusted installers”.

However it doesn’t work, Cygwin behaves as if it failed to load all bash.exe’s dependencies.
However if enable “Automatically detect the installers / updaters and run them outside the Sandbox” and disable “Automatically trust the files from the trusted installers”, it works as expected.

So… Any idea why?

This could be a related topic: D+ Rules with groups not working for me in 5.3.174622.1216.