If I download a .deb file from a website, does it have some kind of information to connect to a server of theirs and automatically update itself when I run apt-get upgrade?
I am just wondering whether I should always go for adding repositories over downloading a .deb.
(Mainly because I want the latest versions of some software not yet updated in the Mint/Ubuntu repositories e.g. Clementine).
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No, a .deb file is just that--a certain version of a program that you can install to your system. You will also be able to remove it again through Software Manager, Synaptic, or similar package management tools. It won't automatically update unless the same package is also available in one of your repositories, and has a higher version number there. Hence you generally add a repository, so that you get upgrades for your program as well