Passphrase works once, then is rejected every time.
OpenPGP addon for Mozilla Thunderbird
Brought to you by:
pbrunschwig
Menu
▾
▴
I set up Enigmail with the latest Thunderbird on Windows 7 x64 and imported my private keys from an OS X laptop. Initially it worked, but after a certain period had expired (I'd assume the default 5 minute time-out?), it'd ask for the passphrase again, but this time it would reject it every single time without an error message.
Uninstalling and reinstalling Gpg4Win would fix it for this initial 5-minute period. Eventually I installed Gpg4Win 1.4 and everything is working again as it should.
Considering that OpenPGP 1 isn't supported much longer by Enigmail, I'd like to solve this problem, but beyond diving into the guts of Gpg4win/OpenPGP I am not really sure where to start. Any kind of hints for solving this problem would be welcome.
How many key pairs (public + private key) do you own? Perhaps it is asking you the passphrase for a different private key.
I just have one private key, which I only use for my work account. I have also tried changing the passphrase on the OS X system, transfer the private key to the Windows system and reimport it there.
On a fresh installation of Gpg4Win this will work correctly the first time, with the passphrase being accepted and the emails being decrypted, yet after the expiration time the subsequent attempts to input the same passphrase are rejected every time until Gpg4Win is uninstalled and installed again.
Please attach a debug log file; I'll try to see if there is some useful output from GnuPG. Menu Enigmail > Debugging Options > View Log
To enable the log file, you must first go to Enigmail > Preferences > Display Expert Settings and Menu > Debugging, then enter a path in Log Directory.
Do you have multiple Region/Language keyboards configured? If yes, please check that the correct one is selected when entering your passphrase.
Just a guess, trying to narrow down the problem as it's a strange issue.
Last edit: Daniele Raffo 2015-05-17
To get some logging information I needed to first reinstall Gp4Win 2.x. For this I got the latest version directly from the Gpg4win website and installed it alongside the 1.x version, then switched the path to the PGP executable (gpg.exe to gpg2.exe in their respective folders). Enigmail now behaves properly with Gpg4win 2.x.
Only difference here is that I installed Gpg4win myself instead of letting the Wizard download and install it. I do not know which version it downloads, but it appears that there's a problem there somewhere. I noticed that with the manually installed Gpg4win 2.x the Pin input dialogue also looks completely different from when I let Enigmail install it.
Hopefully this helps.