GPGMail: NordVPN overriding private key passphrase?!

Michael Clarke's Avatar

Michael Clarke

24 Aug, 2017 06:19 AM

I am using NordVPN, and when I attempted to send an encrypted email while connected to the VPN, the mail was sent apparently encrypted without GPG Mail asking me to input my private key passphrase.

I expect GPG Mail to ask me for my private key passphrase before sending an encrypted email.

Additional info
I do not have my private key passphrase saved in my MacOS keychain, and I had not recently entered my passphrase so I am confident it was not cached. In my sent mail, if I attempt to view these encrypted sent messages, GPG Mail asks me for my passphrase. It appears that NordVPN somehow circumvented GPG Mail’s passphrase challenge and sent encrypted emails as if they were authenticated. This is very bad. What is going on?

macOS           10.12.6     16G29
GPG Suite       2017.1b3    1812    (d43863c)
GPGMail         2.7b3       1215    (d0b5fa0)
GPG Keychain    1.3.3b2     1271    (028a4a2)
GPGServices     1.11        916     (872e77d)
MacGPG2         2.0.30-1b2  887-    (4912d26)
GPGPreferences  2.0.2b3     927     (641418e)
Libmacgpg       0.7         782     (536bf51)
pinentry        0.9.7       4       (b75069d)
  1. 1 Posted by Michael Clarke on 24 Aug, 2017 07:08 AM

    Michael Clarke's Avatar

    I can't replicate this error... perhaps I did something wrong the first time. Now everything seems to work properly.

  2. Support Staff 2 Posted by Steve on 25 Aug, 2017 12:06 PM

    Steve's Avatar

    Hi Michael,

    welcome to the GPGTools support platform. Sorry you are having problems using GPG Suite.

    Please see this KB-article on how to manage passwords for your keys.

    Maybe the caching time was at play?

    All the best,

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