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I'm using Emacs 25.1 on fresh Debian Unstable installation. I have gnupg installed on my system, and twittering-use-master-password is t. When I invoke M-x twit, a web page with an application PIN is opened, and I must enter that PIN in Emacs. After I authorize the application, I get the following messages:

Open authorization URL with browser? (using `browse-url') (y or n) y
Authorization for the account "gnuvince" succeeded.
Encrypting......
(Encrypt failed Exit)
Loading international/kinsoku...done
Fetching :home. Success. :home: +20
Fetching :home. Success. (No new tweets)

Encryption used to work on my former laptop, does anyone know why the encryption would fail now?

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From GnuPG 2.1 two software should be used: gpg-agent and pinentry.

Update the files as follows:

$ echo 'allow-loopback-pinentry' >> ~/.gnupg/gpg-agent.conf
$ echo 'pinentry-mode loopback' >> ~/.gnupg/gpg.conf

Restart gpg-agent:

$ gpgconf --kill gpg-agent

It worked for me on Emacs24 / FreeBsd11, but it should work on GNU / Linux as well.

Source: https://blog.web-apps.tech/emacs-mac-twittering-mode-every-asked-pin/

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My solution to this problem, generate a key with gpg:

$ gpg --generate-key
gpg (GnuPG) 2.2.0; Copyright (C) 2017 Free Software Foundation, Inc.
This is free software: you are free to change and redistribute it.
There is NO WARRANTY, to the extent permitted by law.

Note: Use "gpg --full-generate-key" for a full featured key generation dialog.

GnuPG debe construir un ID de usuario para identificar su clave.

Nombre y apellidos: Manuel Kaufmann
[snip]

Then, log in with twittering-mode and use the same phrase you just generated. It will success and that's it.

Enjoy!

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