I'm a Vista Home user who is new to GNU PGP (version 2.0.17 with Cleopatra 2.1.0 / GPA 0.9.1-svn1024). When I work on more than one file a few minutes apart, gpg reuses my passphrase via a cache and only prompts for it randomly via the pinentry dialog. That's fine the few times things are working, but the cache often fails in some way, and pinentry is nowhere to be seen to correct the bad passphrase GPG is using. The result is I get a "bad passphrase" error from the GUI and fail to get a working encryption/decryption. At that point I have to wait about 10 minutes until pinentry decides to pop up again, while every attempt to encrypt / decrypt keeps failing with said error. I only do "Encrypt" and "Sign and Encrypt" via the explorer shell, choosing myself as recipient and using a single key to encrypt.

Anyone else having this problem with my version of GPG? Is there some way to "flush" the passphrase, forcing pinentry to reappear so I can consistently complete my tasks?

gpg.exe doesn't seem to have options to force pinentry to flush the cache. I find its CLI options very complicated, so I can't really test whether the CLI is affected... I do remember that gpg has the power to trigger pinentry as well as fail when the passphrase has the problem.

It seems it's not a botched install. I installed two separate downloads at two different sites the past week about 12 hours apart.

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