Why the "catch" isn't documented anywhere?

There's another catch here : If the proxy setting needs to be of the
same type as the URL, how exactly am I supposed to know in advance when
querying the information?

As you can imagine, the /etc/apt/souces.list.d is filed with mixed
content such as HTTP and HTTPS so how can I sort this out?

I've made a quick test and there's nothing in the environment nor
arguments passed to "app" that would help make the decision.

Anyway, given the info you provide, even if I decide to go full HTTPS on
the proxy, this would break the classic HTTP URLs.

This sounds like a big design mistake here... this forces people to
HARDCODE things in configuration which really bad design :-(

What's so harmful in using an HTTP proxy to fetch data from an HTTPS
URL? That's just a proxy to get Internet access, nothing more, because
depending on the environment, you may have (or not) direct Internet
access, hence the use of Proxy-Auto-Detect.

You really need to reconsider this!

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https://bugs.launchpad.net/bugs/1656352

Title:
  apt does not honor Proxy-Auto-Detect for HTTPS URLs

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