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What's the proper way to install Enigmail (PGP Signing for Thunderbird)? I noticed that it's in the Ubuntu repositories - is that the proper way to install it, or should I install it from the page on the Thunderbird Addons site? Or does it not matter at all?

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On enigmail.net they say

Thunderbird on Linux Many Linux distributions ship with their own customized version of Thunderbird. If you use your distribution's version of Thunderbird, you must use your distribution's version of Enigmail. If you get Thunderbird from the official site and install it yourself, though, you can use the official Enigmail releases provided by the Enigmail Project.

Based on that I'd install from repos if that's how you got TB.

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I would recommend that you use the version from the add-ons website. It will be more current that whatever's in the repos and t-bird will check to see if there are updates for it.

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