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How much can I get away with before I break Debian?
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So while it's true you shouldn't use third party repos. If you look at your vpn and you have any version dependencies it will install then eventually you will have a bad time. But if it's just a self-contained package you should be fine. Worse case it may uninstall the vpn when you do an upgrade. Where people get in trouble is when they install ubuntu repos thinking they are synonyms for Debian or worse install testing or sid next to stable.
Just remember to just read carefully when doing an upgrade and turn off unattended upgrades as that's where most breaks happen. You have to check what packages are Bing added or removed and which packages are held back. Sometimes they are held back due to the package installed in that 3rd party Repo. You can test this by running apt -s install package listed as held back in the upgrade and see what error you get to see the package breaking it.
Learning about apt pinning woll also help you not break Debian.
Cool never looked into apt pinning but seems pretty interesting.
Looking at what I install as self contained packages vs requiring dependencies made this a lot more clear. Thanks!
Cool yeah the main problem everyone seems is someone installs debian stable get frustrated it's got old stable packages and trys to add testing Repo or a PPA from ubuntu and then brick their systems. If you have a good grasp you can mix repos.
Like my home desktop I run a mix of testing, unstable, and experimental and Pin stuff from unstable and experimental when needed. Note I would never do that going between stable and testing as the packages are too far apart depending on where we see in the release process. But since testing and unstable are normally just a fewer weeks off nothing breaks. But I treat it like I'm running on unstable like using apt-listbugs and apt-listchanges to confirm everything when I update.