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29 votes
1 answer
15k views

How does S/MIME differ from PGP/GPG, for the purpose of signing and/or encrypting email?

In addition to the titular question, are the two technologies compatible? If so, under what circumstances? What are the relative benefits of the two technologies?
user avatar
10 votes
3 answers
4k views

Is it possible to associate a secondary email address with an existing *public* key?

For example, if I have a friend's public key that's associated with, say, email address [email protected], but I want to send him a message at [email protected], is there a sensible way to do this? Is ...
Chris W.'s user avatar
  • 203
9 votes
4 answers
6k views

Enigmail cannot communicate with gpg-agent

Update As of Ubuntu 16.04, the plug-in works as expected and there's no need to downgrade as suggested in the accepted answer. The question was applicable to Ubuntu 15.04 and, maybe, 15.10. Original ...
code_dredd's user avatar
9 votes
1 answer
2k views

How do I prevent Enigmail from encrypting my email, even when encryption is turned off?

Enigmail add-on to Thunderbird is encrypting all emails, even when encryption is turned off. I save the email as a draft, and when I view it in Drafts folder (or if it was sent), then it shows as ...
Chloe's user avatar
  • 6,046
8 votes
3 answers
2k views

saving and searching encrypted mail

I often send and receive gpg-encrypted mail. At the moment I use thunderbird + enigmail (in linux) to do that. As far as I know there is no way in thunderbird to find all encrypted messages which ...
student's user avatar
  • 475
7 votes
2 answers
6k views

Integrate GnuPG with Outlook

I want to integrate GnuPG with Outlook in such a way that when it receives an email, it must automatically decrypt the mail using my private key and display on-screen.
RPK's user avatar
  • 2,753
7 votes
3 answers
5k views

Mutt with GPG Password Protection

I got Mutt working with the default IMAP password management configuration with this line in my config: set imap_pass = XXXX Which is obviously not secure. I looked at this https://wiki.archlinux....
bashirs's user avatar
  • 171
2 votes
1 answer
248 views

In what real-life environments is GPG email signing used? [closed]

I've been using e-mail for over a decade in a regular business environment, but I can not remember having seen any invitation from anybody to GPG sign my e-mails (or somebody who offered to send GPG-...
please delete me's user avatar
2 votes
1 answer
112 views

GnuPG Domain to Domain email encryption

I'm running a Debian mail server and am looking forward to encrypt mails from my domain to the domain of a business partner. Also, the encryption should happen on the mail server itself not on a mail ...
Endo's user avatar
  • 21
2 votes
1 answer
3k views

Using OpenSSL to generate encryption key for Outlook users

A private web application needs to receive encrypted email from perhaps 20 known users. How can I use OpenSSL to generate a valid encryption certificate that Outlook users can import and use to ...
CodeMed's user avatar
  • 354
2 votes
0 answers
68 views

Mail encryption on Windows RT

Is it somehow possible to use mail encryption preferably via GPG on Windows RT? Since on a Windows RT Surface tablet you only have access to Windows Mail as an app in the store, there is no fancy ...
S818's user avatar
  • 121
1 vote
1 answer
2k views

GPG Keys and Emails

I have been testing out GPG keys and were studying the changes of the keys when adding/removing users on the key. If I add a user Alice upon key generation. I export the key pairs's public and private ...
abhobe's user avatar
  • 63
1 vote
1 answer
139 views

GPG keys for mailinglists

There are two mailing-lists (e.g. [email protected] and [email protected]) for which I'd like to generate GPG keys and send the respective private keys to the members of the lists, so mails to the lists can ...
mcantsin's user avatar
  • 135
1 vote
2 answers
2k views

Is there a guide to setting up Mozilla Thunderbird to use my GPG keys to sign and/or encrypt email messages on Windows?

I see instructions on websites and questions here about using GPG keys with Thunderbird in Linux, but nothing on Windows. I have GPG, Kleopatra, and Thunderbird 3 installed on Windows, I made my GPG ...
Thomas Owens's user avatar
  • 3,894
1 vote
0 answers
360 views

No prompt for setting a passphrase in GPG Keychain

I am trying to use GPG Keychain with Thunderbird (version 60.5.1) and Enigmail (version 2.0.9 / 20181209-1409). In the process of generating a key for the email address after setting the password and ...
Stoowea's user avatar
  • 11

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