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So, I've been using Debian with apt for quite some time, and I don't really have a good sense of understanding around apt and how it manages packages and dependencies.

What I really want is to simulate conflicts that apt can't seem to deal with on its own, forcing me to sort them out manually, preferably using a multitude of tools (dpkg, aptitude, apt, and/or manually moving/removing/installing packages) to methodically resolve the issues.

I hear that during distro upgrades apt can be a pain but frankly I haven't noticed that. Maybe I've been lucky or maybe I just backed up my data and fresh-installed; I don't know. Either way, dependency hell is a place I'd like to go just for the practice of getting myself out.

What's a good, reliable way to simulate these issues?

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Use dpkg directly to:

  1. Install a package which misses dependencies.
  2. Upgrade only one piece of a package, i.e. update libc6-dev but leave libc6.
  3. Remove a package which other packages depend on.
  4. Downgrade a library from the current newer version of which other libraries/applications depend.

There must be other funkier ways to break dependencies.

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