Hi there,

I've had this issue a couple of times and always was able to fix it by
upgrading GnuPG for OSX, but I'm already on v2.1.7.

I first cleared the saved password in Enigmail, but that didn't help.

The I had a look at
https://enigmail.net/index.php/en/faq?view=topic&id=14 "Resolving issues
with GnuPG 2.x and gpg-agent", but that didn't point me to any solution
either.

I'm using Thunderbird 45.6.0 with Enigmail 1.9.6.1, below are the logs.

Any help would be appreciated.

Best,
Nick

> 2017-01-23 16:18:20.977 [DEBUG] enigmailMsgComposeOverlay.js: 
> Enigmail.msg.sendMessageListener
> 2017-01-23 16:18:20.977 [DEBUG] enigmailMsgComposeOverlay.js: 
> Enigmail.msg.handleSendMessageEvent
> 2017-01-23 16:18:20.978 [DEBUG] enigmailMsgComposeOverlay.js: 
> Enigmail.msg.encryptMsg: msgSendType=0, Enigmail.msg.sendMode=1, 
> Enigmail.msg.statusEncrypted=0
> 2017-01-23 16:18:20.978 [DEBUG] enigmailMsgComposeOverlay.js: 
> Enigmail.msg.encryptMsg: currentId=[nsIMsgIdentity: id3], [email protected]
> 2017-01-23 16:18:20.978 [DEBUG] enigmailMsgComposeOverlay.js: 
> Enigmail.msg.encryptMsg:gMsgCompose=[xpconnect wrapped nsIMsgCompose]
> 2017-01-23 16:18:20.979 [DEBUG] =====> keySelection()
> 2017-01-23 16:18:20.979 [DEBUG] enigmailMsgComposeOverlay.js: 
> Enigmail.msg.keySelection()
> 2017-01-23 16:18:20.979 [DEBUG] enigmailMsgComposeOverlay.js: 
> Enigmail.msg.keySelection(): toAddrStr="[email protected]" bccAddrStr=""
> 2017-01-23 16:18:20.980 [DEBUG] =====> processRules()
> 2017-01-23 16:18:20.980 [DEBUG] enigmailMsgComposeOverlay.js: 
> Enigmail.msg.processRules(): toAddrStr="[email protected]" bccAddrStr="" 
> forceRecipientSettings=false
> 2017-01-23 16:18:20.980 [DEBUG] rules.jsm: mapAddrsToKeys(): 
> emailAddrsStr="[email protected]" startDialogForMissingKeys=false
> 2017-01-23 16:18:20.980 [DEBUG] rules.jsm: getRulesData()
> 2017-01-23 16:18:20.980 [DEBUG] rules.jsm: getRulesFile()
> 2017-01-23 16:18:20.980 [DEBUG]    found keys:
> 2017-01-23 16:18:20.980 [DEBUG]    addresses without keys:
> 2017-01-23 16:18:20.980 [DEBUG]      [email protected]
> 2017-01-23 16:18:20.980 [DEBUG]    old returned value:
> 2017-01-23 16:18:20.980 [DEBUG]      
> 2017-01-23 16:18:20.980 [DEBUG] enigmailMsgComposeOverlay.js: 
> Enigmail.msg.processFinalState()
> 2017-01-23 16:18:20.980 [DEBUG] enigmailMsgComposeOverlay.js:   encrypt=false 
> encryptByRules=1 encFinally=0
> 2017-01-23 16:18:20.980 [DEBUG]                                 encReason=
> 2017-01-23 16:18:20.980 [DEBUG] enigmailMsgComposeOverlay.js:   signed=true 
> signByRules=1 signFinally=1
> 2017-01-23 16:18:20.980 [DEBUG]                                 
> signReason=enabled by default
> 2017-01-23 16:18:20.980 [DEBUG] enigmailMsgComposeOverlay.js:   
> pgpmimeByRules=1 pgpmimeFinally=1
> 2017-01-23 16:18:20.980 [DEBUG] rules.jsm: mapAddrsToKeys(): emailAddrsStr="" 
> startDialogForMissingKeys=false
> 2017-01-23 16:18:20.981 [DEBUG] rules.jsm: getRulesData()
> 2017-01-23 16:18:20.981 [DEBUG] rules.jsm: getRulesFile()
> 2017-01-23 16:18:20.981 [DEBUG]    found keys:
> 2017-01-23 16:18:20.981 [DEBUG]    addresses without keys:
> 2017-01-23 16:18:20.981 [DEBUG]    old returned value:
> 2017-01-23 16:18:20.981 [DEBUG]      
> 2017-01-23 16:18:20.981 [DEBUG]   <=== processRules()
> 2017-01-23 16:18:20.981 [DEBUG] enigmailMsgComposeOverlay.js: 
> Enigmail.msg.keySelection(): return toAddrStr="[email protected]" 
> bccAddrStr=""
> 2017-01-23 16:18:20.981 [DEBUG]   <=== keySelection()2017-01-23 16:18:20.981 
> [DEBUG] enigmailMsgComposeOverlay.js: hasAttachments = false
> 2017-01-23 16:18:20.981 [DEBUG] enigmailMsgComposeOverlay.js: 
> Enigmail.msg.encryptMsg: Using PGP/MIME, flags=225
> 2017-01-23 16:18:20.981 [DEBUG] enigmailMsgComposeOverlay.js: 
> Enigmail.msg.encryptMsg: oldSecurityInfo = [xpconnect wrapped 
> nsIMsgSMIMECompFields]
> 2017-01-23 16:18:20.982 [DEBUG] enigmailMsgComposeOverlay.js: 
> Enigmail.msg.encryptMsg: securityInfo = [xpconnect wrapped 
> nsIEnigMsgCompFields]
> 2017-01-23 16:18:20.982 [DEBUG] enigmailMsgComposeOverlay.js: 
> Enigmail.msg.encryptMsg: enabled forceMsgEncoding
> 2017-01-23 16:18:21.017 [DEBUG] hash.jsm: determineAlgorithm
> 2017-01-23 16:18:21.017 [DEBUG] encryption.jsm: encryptMessageStart: 
> uiFlags=16, from 0x7BC2627E to , hashAlgorithm=null (00000101)
> 2017-01-23 16:18:21.017 [DEBUG] encryption.jsm: determineOwnKeyUsability: 
> sendFlags=257, sender=0x7BC2627E
> 2017-01-23 16:18:21.017 [DEBUG] keyRing.jsm: getKeyById: 0x7BC2627E
> 2017-01-23 16:18:21.017 [DEBUG] encryption.jsm: getEncryptCommand: 
> hashAlgorithm=null
> 2017-01-23 16:18:21.018 execution.jsm: execStart: command = 
> /usr/local/bin/gpg2 --charset utf-8 --display-charset utf-8 --use-agent 
> --batch --no-tty --status-fd 2 -t --clearsign -u 0x7BC2627E, 
> needPassphrase=1, domWindow=[object ChromeWindow], listener=[object Object]
> 2017-01-23 16:18:21.018 [CONSOLE] enigmail> /usr/local/bin/gpg2 --charset 
> utf-8 --display-charset utf-8 --use-agent --batch --no-tty --status-fd 2 -t 
> --clearsign -u 0x7BC2627E
> 2017-01-23 16:18:21.044 [DEBUG]   enigmail> DONE
> 2017-01-23 16:18:22.923 [DEBUG] encryption.jsm: encryptMessageEnd: 
> uiFlags=16, sendFlags=00000101, outputLen=10
> 2017-01-23 16:18:22.923 [DEBUG] errorHandling.jsm: parseErrorOutputWith: 
> status message: 
> [GNUPG:] KEY_CONSIDERED 59DF4B8185C293600250CC03A47E0BA87BC2627E 2
> [GNUPG:] BEGIN_SIGNING H8
> gpg: signing failed: No pinentry
> [GNUPG:] FAILURE sign 67108949
> gpg: [stdin]: clear-sign failed: No pinentry
> 
> 2017-01-23 16:18:22.923 [DEBUG] system.jsm: determineSystemCharset
> 2017-01-23 16:18:22.923 [DEBUG] system.jsm: determineSystemCharset: 
> charset='iso-8859-1'
> 2017-01-23 16:18:22.923 [DEBUG] errorHandling.jsm: parseErrorOutputWith: 
> statusFlags = 00400000
> 2017-01-23 16:18:22.923 [DEBUG] errorHandling.jsm: parseErrorOutputWith: 
> return with c.errorMsg = gpg: signing failed: No pinentry
> 2017-01-23 16:18:22.923 [DEBUG] execution.jsm: EnigmailExecution.fixExitCode: 
> agentType: gpg exitCode: 2 statusFlags 4194304
> 2017-01-23 16:18:22.923 [DEBUG] encryption.jsm: encryptMessageEnd: command 
> execution exit code: 2
> 2017-01-23 16:18:24.791 [ERROR] mimeEncrypt.js: caught exception: undefined
> Message: 'undefined'
> File:    undefined
> Line:    undefined
> Stack:   undefined
> 2017-01-23 16:18:26.676 [DEBUG] enigmailMsgComposeOverlay.js: 
> ECSL.ComposeProcessDone: 2147500037
> 2017-01-23 16:18:26.676 [DEBUG] enigmailMsgComposeOverlay.js: 
> Enigmail.msg.removeAttachedKey: 
> 2017-01-23 16:18:29.462 [DEBUG] enigmailMessengerOverlay.js: 
> updateOptionsDisplay: 
> 2017-01-23 16:18:29.462 [DEBUG] funcs.jsm: collapseAdvanced:
> 2017-01-23 16:18:30.410 [DEBUG] enigmailMessengerOverlay.js: 
> updateOptionsDisplay: 
> 2017-01-23 16:18:30.410 [DEBUG] funcs.jsm: collapseAdvanced:
> 2017-01-23 16:18:31.667 [DEBUG] enigmailHelp.js: enigLoadPage
> 2017-01-23 16:18:31.667 [DEBUG] enigmailCommon.jsm: getFrame: 
> name=contentFrame


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