"GnuPG cannot query your passphrase via pinentry.", please help.

[Supamon Holmes]

Dear All,

My Enigmail does not work anymore. Today I receive an error message "GnuPG cannot query your passphrase via pinentry" when I tried to send an encrypted email. I am running Enigmail version 2.0.7 (20180612-1520), Thunderbird 52.8.0(64-bit), machine macOS High Sierra version 10.13.5.

The error message appeared when clicking send message, never have a chance to put passphase. I would be grateful for any advices.

Regards,
S Holmes

[Patrick Brunschwig]

I recommend the FAQ topic about Resolving issues with GnuPG 2.x and gpg-agent:
https://enigmail.net/index.php/en/faq-en?view=topic&id=14

[Supamon Holmes]

**Many thanks for your advice. I followed the link and the instructions on Troubleshooting page and find the below in Debugging Options > View Log
**

---

2018-07-01 13:59:58.426 [DEBUG] encryption.jsm: encryptMessageEnd: uiFlags=16, sendFlags=00000162, outputLen=1244
2018-07-01 13:59:58.426 [DEBUG] errorHandling.jsm: parseErrorOutputWith: status message:
[GNUPG:] KEY_CONSIDERED 1DCAB8AD5CF0DCD721006D2825B70B270AF98B52 0
[GNUPG:] KEY_CONSIDERED 622A4B86BA3B7708660246BBBF2EF3FBAF4E5E71 0
[GNUPG:] ENCRYPTION_COMPLIANCE_MODE 23
[GNUPG:] PROGRESS need_entropy X 32 128
[GNUPG:] PROGRESS need_entropy X 128 128
[GNUPG:] BEGIN_ENCRYPTION 2 7
[GNUPG:] END_ENCRYPTION

2018-07-01 13:59:58.428 [DEBUG] errorHandling.jsm: parseErrorOutputWith: statusFlags = 80000000
2018-07-01 13:59:58.428 [DEBUG] errorHandling.jsm: parseErrorOutputWith: return with c.errorMsg =
2018-07-01 13:59:58.428 [DEBUG] execution.jsm: EnigmailExecution.fixExitCode: agentType: gpg exitCode: 0 statusFlags -2147483648
2018-07-01 13:59:58.428 [DEBUG] encryption.jsm: encryptMessageEnd: command execution exit code: 0
2018-07-01 13:59:58.428 [DEBUG] <=== encryptMessage()
2018-07-01 13:59:58.428 [DEBUG] <=== encryptTestMessage()
2018-07-01 13:59:58.428 [DEBUG] enigmailMsgComposeOverlay.js: Enigmail.msg.keySelection(): return toAddrStr="0xBF2EF3FBAF4E5E71" bccAddrStr=""
2018-07-01 13:59:58.428 [DEBUG] <=== keySelection()
2018-07-01 13:59:58.428 [DEBUG] enigmailMsgComposeOverlay.js: hasAttachments = false
2018-07-01 13:59:58.428 [DEBUG] enigmailMsgComposeOverlay.js: Enigmail.msg.encryptMsg: Using PGP/MIME, flags=227
2018-07-01 13:59:58.428 [DEBUG] enigmailMsgComposeOverlay.js: Enigmail.msg.encryptMsg: oldSecurityInfo = [xpconnect wrapped nsIMsgSMIMECompFields]
2018-07-01 13:59:58.430 [DEBUG] enigmailMsgComposeOverlay.js: Enigmail.msg.encryptMsg: securityInfo = [xpconnect wrapped nsISupports]
2018-07-01 13:59:58.430 [DEBUG] enigmailMsgComposeOverlay.js: Enigmail.msg.encryptMsg: enabled forceMsgEncoding
2018-07-01 13:59:58.458 [DEBUG] mimeEncrypt.js: requiresCryptoEncapsulation
2018-07-01 13:59:58.482 [DEBUG] mimeEncrypt.js: requiresCryptoEncapsulation
2018-07-01 13:59:58.484 [DEBUG] mimeEncrypt.js: beginCryptoEncapsulation
2018-07-01 13:59:58.484 [DEBUG] mimeEncrypt.js: startCryptoHeaders
2018-07-01 13:59:58.484 [DEBUG] mimeEncrypt.js: encryptedHeaders
2018-07-01 13:59:58.490 [DEBUG] mimeEncrypt.js: finishCryptoEncapsulation
2018-07-01 13:59:58.492 [DEBUG] encryption.jsm: encryptMessageStart: uiFlags=9, from 0x25B70B270AF98B52 to 0xBF2EF3FBAF4E5E71, hashAlgorithm=null (000010e3)
2018-07-01 13:59:58.492 [DEBUG] encryption.jsm: determineOwnKeyUsability: sendFlags=4323, sender=0x25B70B270AF98B52
2018-07-01 13:59:58.492 [DEBUG] keyRing.jsm: getKeyById: 0x25B70B270AF98B52
2018-07-01 13:59:58.492 [DEBUG] encryption.jsm: getEncryptCommand: hashAlgorithm=null
2018-07-01 13:59:58.494 execution.jsm: execStart: command = /usr/local/gnupg-2.2/bin/gpg2 --charset utf-8 --display-charset utf-8 --no-auto-check-trustdb --batch --no-tty --no-verbose --status-fd 2 --log-file /private/var/folders/t6/gy5yt1j54d54l5b43fj18v040000gp/T/gpgOutput.HXA9ge -a -t --encrypt --sign --trust-model always --encrypt-to 0x25B70B270AF98B52 -r 0xBF2EF3FBAF4E5E71 -u 0x25B70B270AF98B52, needPassphrase=1, domWindow=[object ChromeWindow], listener=[object Object]
2018-07-01 13:59:58.494 [CONSOLE] enigmail> /usr/local/gnupg-2.2/bin/gpg2 --charset utf-8 --display-charset utf-8 --no-auto-check-trustdb --batch --no-tty --no-verbose --status-fd 2 --log-file /private/var/folders/t6/gy5yt1j54d54l5b43fj18v040000gp/T/gpgOutput.HXA9ge -a -t --encrypt --sign --trust-model always --encrypt-to 0x25B70B270AF98B52 -r 0xBF2EF3FBAF4E5E71 -u 0x25B70B270AF98B52
2018-07-01 13:59:58.496 [DEBUG] enigmail> DONE
2018-07-01 13:59:58.962 [DEBUG] errorHandling.jsm: Process terminated. Human-readable output from gpg:

---

2018-07-01 13:59:58 gpg[26262] signing failed: No pinentry
2018-07-01 13:59:58 gpg[26262] [stdin]: sign+encrypt failed: No pinentry

---

2018-07-01 13:59:58.962 [DEBUG] mimeEncrypt.js: done: 2
2018-07-01 13:59:58.962 [DEBUG] encryption.jsm: encryptMessageEnd: uiFlags=9, sendFlags=000010e3, outputLen=1109
2018-07-01 13:59:58.962 [DEBUG] errorHandling.jsm: parseErrorOutputWith: status message:
[GNUPG:] KEY_CONSIDERED 1DCAB8AD5CF0DCD721006D2825B70B270AF98B52 2
[GNUPG:] KEY_CONSIDERED 1DCAB8AD5CF0DCD721006D2825B70B270AF98B52 0
[GNUPG:] KEY_CONSIDERED 622A4B86BA3B7708660246BBBF2EF3FBAF4E5E71 0
[GNUPG:] PROGRESS need_entropy X 32 128
[GNUPG:] PROGRESS need_entropy X 128 128
[GNUPG:] BEGIN_SIGNING H8
[GNUPG:] BEGIN_ENCRYPTION 2 7
[GNUPG:] FAILURE sign-encrypt 67108949

2018-07-01 13:59:58.964 [DEBUG] errorHandling.jsm: parseErrorOutputWith: statusFlags = 00400000
2018-07-01 13:59:58.964 [DEBUG] errorHandling.jsm: parseErrorOutputWith: return with c.errorMsg =
2018-07-01 13:59:58.964 [DEBUG] execution.jsm: EnigmailExecution.fixExitCode: agentType: gpg exitCode: 2 statusFlags 4194304
2018-07-01 13:59:58.964 [DEBUG] encryption.jsm: encryptMessageEnd: command execution exit code: 2
2018-07-01 13:59:58.982 [DEBUG] enigmailCommon.jsm: dispatchEvent f=resizeDlg
2018-07-01 14:00:01.218 [ERROR] mimeEncrypt.js: caught exception: undefined

---

**At Terminal I typed the script below (as shown on the website) and nothing happened. **

iMac:~ sholmes$ pinentry <<EOT

SETDESC Hello World
CONFIRM
EOT
-bash: pinentry: command not found
iMac:~ sholmes$

I am stuck at the moment and will be grateful for any further suggestions.

[Patrick Brunschwig]

Pinentry on macOS is a little more complicated. My first recommendation is the following:
edit the file ~/.gnupg/gpg-agent.conf and remove any lines starting with pinentry-program. Then execute killall gpg-agent.

[Supamon Holmes]

Just would like to let you know that there is no lines starting with pinentry-program in ~/.gnupg/pgp-agent.conf. However, I excuted "killall gpg-agent" and it works! I think that I should attached the information below from ~/.gnupg/pgp-agent.conf for your information.
Thank you very much for all your help and support. Enigmail is working well now.

# Created by pEpEngine
# GPGConf disabled this option here at Sat Jun 23 12:19:46 2018 BST
# default-cache-ttl 300
# GPGConf disabled this option here at Sat Jun 23 12:19:46 2018 BST
# max-cache-ttl 1200

###+++--- GPGConf ---+++###
default-cache-ttl 300
max-cache-ttl 3000
###+++--- GPGConf ---+++### Sat Jun 23 12:19:46 2018 BST
# GPGConf edited this configuration file.
# It will disable options before this marked block, but it will
# never change anything below these lines.

[JOS]

Dear all,

I have the same problem, I have to enter my PGP passphrase again and again. Here is my configuration:

• OS: macOS Mojave, Version 10.15.5
• Thunderbird: Version 60.7.1
• Enigmail: Enigmail version 2.0.11 (20190521-1529)
  Using gpg executable /usr/local/gnupg-2.2/bin/gpg2 to encrypt and decrypt

When I excute "killall gpg-agent” in a terminal, it seems to work for several minutes without having to enter the passphrase again but after a while I need to re-enter passphrases.

This is my mpg-agent.conf file:

# File re-created by pEp
# See backup in '/Users/UserName/.gnupg/gpg-agent.conf.0.pep.bkp'

default-cache-ttl 300
max-cache-ttl 999999
use-standard-socket

Any ideas on how to solve this problem are appreciated!?

JOS

[Patrick Brunschwig]

default-cache-ttl 300 is 5 minutes (= 300 seconds). Set that to a higher value, such as 30000.

[JOS]

Thank you very much, this works for me! JOS