Enigmail / Forum / Enigmail Support: Resolving Issues with Enigmail after Upgrading

Patrick Brunschwig - 2016-02-28

If you get error messages like those below after upgrading to Enigmail version 1.9 / 1.8:

GnuPG reported an error in the communication with gpg-agent (A component of GnuPG)

Error - no matching private/secret key found to decrypt message

Send operation aborted. Error - encryption command failed

Send operation aborted. Key 0x....... not found or not valid. The (sub-)key might have expired

then please read our Guide for resolving issues with GnuPG 2.x and gpg-agent.

Last edit: Patrick Brunschwig 2016-11-28
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Jörg Jenetzky - 2016-10-02

Hi everybody.

Using TB 45.3.0, Enigmail 1.9.5 on

inxi CPU~Quad core Intel Core i5-3470 (-MCP-) speed/max~3415/3600 MHz Kernel~3.19.0-32-generic x86_64 Up~2:37 Mem~2539.8/7918.5MB HDD~2750.6GB(55.8% used) Procs~212 Client~Shell inxi~2.2.28

I cannot decrypt sent msgs, not send msg to myself.
Passphrases won't be accepted.
Gpg-agent is installed.
See attached screenshot for error msg.

It seems related to the last update of Firefox (-> v. 49.0, just yesterday), since the problem appeared after that.

Any hints?

20161002_141536_sc_Enigmail_Error.png
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Patrick Brunschwig - 2016-10-02

Enigmail is installed in Thunderbird, not Firefox - there is no relationship between Enigmail and Firefox in any way.

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- Jörg Jenetzky - 2016-10-02
  
  Well the, it may be not related, though it appeared coincidentally (I have Mailvelope 1.5.2 installed in FF, though, which I thought might interfere eventually). Just wanted to tell everything of meaning.
  
  Anyway, I don't want to mess everything up by trying bold things, on the other hand I badly need access to my email.^^
  
  Weekly backups available, Enigmail would just not access hidden folders (such as .thunderdird...).
  
  Last edit: Jörg Jenetzky 2016-10-02
  
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  - Ludwig Hügelschäfer - 2016-10-02
    
    Well, it looks like the same update that brought FF 49 broke your gpg-agent setup. Did this work correctly before?
    
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Patrick Brunschwig - 2016-10-02

Then it may have been Mailvelope 1.5.2 making some changes to your GnuPG configuration. We have put all of our knowledge of how to resolve such issues into our Guide for resolving issues with GnuPG 2.x and gpg-agent. Please follow it.

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Jörg Jenetzky - 2016-10-02

@Ludwig: Yes, it did. Eleven months w/ no prob.

Uninstalled Mailvelope 1.5.2 from FF (don't need this s... in the first place).

Went through troubleshooting at https://enigmail.net/index.php/en/faq?view=category&id=14 (though I actually have Enigmail 1.9.5, no 2.x).

Used Simons workaround from https://blog.josefsson.org/2015/01/02/openpgp-smartcards-and-gnome/.

Finally got the gpg-agent working:

gpg-connect-agent <<EOT > GETINFO version > EOT D 2.0.22 OK

and

gpg-connect-agent <<EOT > GET_CONFIRMATION Hello > EOT OK

Still there are either empty (actually displayed seeming empty) or still encrypted mails in my folders.
I have to admit that the debugging does not provide any useful information to me:
(see attachment)
What can I do?

Last edit: Jörg Jenetzky 2016-10-08

20161002_log_Enigmail_gpg-agent_Debug.txt
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- Jörg Jenetzky - 2016-10-08
  
  In the Troubleshooting I find under "8."
  
  If all of the above doesn't help, then get help at our mailing list or our support forum.
  
  My request appears to be unanswered for a week now.
  Still there is no access to my encrypted mail, no keys to be found.
  
  Pretty please: What else can I do?
  
  Last edit: Jörg Jenetzky 2016-10-08
  
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  - Ludwig Hügelschäfer - 2016-10-08
    
    While you produced the above gpg-agent debug listing, did you try to decrypt a mail? If yes, did a pinentry window pop up, asking for your passphrase? If yes, please produce an Enigmail Debug log and attach it here (after maybe removing/obfuscating personal information).
    
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    - Jörg Jenetzky - 2016-10-08
      
      Yes, a few times.
      Every time a pinentry window popped up, asking my passphrase, which I inserted correctly.
      pinentry answered that it was "invalid".
      Output of the gpg-agent debugger as above.
      
      Edit: I was in an error, looked for the tab in the wrong place (is not a register card of the preferences...). The log is very big and I went through it to strip personal information.
      Please see attached.
      (Weared to hang out those logs...)
      
      Last edit: Jörg Jenetzky 2016-10-08
      
      20161008_log_Enigmail_Debug_stripped.txt
      
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Patrick Brunschwig - 2016-10-08

What is the content of your gpg-agent.conf and gpg.conf files?

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- Jörg Jenetzky - 2016-10-08
  
  See attachment for gpg.conf.
  
  Edit: Please see also gpg-agent.conf attached.
  
  Last edit: Jörg Jenetzky 2016-10-08
  
  gpg-agent.conf
  
  gpg.conf
  
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Jörg Jenetzky - 2016-10-08

Klicking on the security info-button produces the attached.
Seems to me as if the secret key was missing.

20161008_200112_sc_Enigmail_Error.png

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Patrick Brunschwig - 2016-10-09

According to the 20161008 log, everything is set up correctly and working properly. The problem is that the passphrase you entered is wrong. I'm sorry, but that's the output from the GnuPG toolchain, and there is no reason to distrust that information.

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- Jörg Jenetzky - 2016-10-09
  
  The behavior of Enigmail changed completely on Oct 2nd, as the mails were not displayed decryted anymore and the passphrase was required, though I have automatical decryption acivated.
  There are three different keys, and all the passphrases are at hand. None works.
  I suspect there are no accessible keys to compare to.
  How can I check on this?
  
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Patrick Brunschwig - 2016-10-09

I assume that your system was configured to use gnome-keyring (or similar) before the setup change. Gnome-keyring stores the password and provides it automatically to gpg if needed. That's possible because it replaces gpg-agent - but unfortunately only with a subset of functions of gpg-agent.

You might be able to recover your password(s) via gnome-keyring (on my Ubuntu it's called "Passwords & Keys").

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Jörg Jenetzky - 2016-10-09

That's correct.
Had to seemingly disable that for activating gpg-agent.

I have now checked there and found that I can change the - by Enigmail so far not accepted - passphrases there.
And guess what: Now it works.
Sheesh.
That is relief.

Thank you very much.

And it is strange: Same passphrases, once rejected, once accepted.
Is there an explanation?

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- Ludwig Hügelschäfer - 2016-10-09
  
  Are there special characters in your passphrase(s), such as Umlauts or other accented characters?
  
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  - Jörg Jenetzky - 2016-10-09
    
    No, nothing like that.
    Upper and lower case, numbers.
    
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Alice Andley - 2019-03-04

I am facing trouble after upgrading to Enigmail. It si not working on my MacBook Pro, so I decided to take help from Apple technical service but did not get the reliable solution. Can I get solution from here?

Last edit: Patrick Brunschwig 2019-03-04

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Patrick Brunschwig - 2019-03-04

This is a support forum, so yes we can try to help you. What precisely is not working? What error message do you get?

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Resolving Issues with Enigmail after Upgrading

OpenPGP addon for Mozilla Thunderbird

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Resolving Issues with Enigmail after Upgrading

Resolving Issues with Enigmail after Upgrading

OpenPGP addon for Mozilla Thunderbird

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Resolving Issues with Enigmail after Upgrading