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

Status in apt package in Ubuntu:
  Triaged

Bug description:
  apt(-get) does not honor Proxy-Auto-Detect configuration in any way
  for HTTPS URLs.

  ex: vi /etc/apt/apt.conf.d/99-proxy-auto-detect

  Acquire::http:Proxy-Auto-Detect "/path/to/app";

  "app" performs some actions and output the name of the proxy server
  according to some internal rules, in the form
  "http://proxy.domain.tld:1234/";

  This works perfectly for all HTTP-like "deb http://example.com/ xxx"
  URLs but is ignored for HTTPS URLs. Setting "Acquire::https:Proxy-
  Auto-Detect" or even the legacy variable name "ProxyAutoDetect"
  (without dashes) does not help either.

  This is very annoying as the very purpose of this auto-detection is to
  be network environment aware instead of using a hardcoded value for
  the proxy setting.

  This should be fixed. Thank you.

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