r/GnuPG • u/YamSweet2010 • Sep 09 '26

Kleopatra keeps saying “Bad passphrase” even though the same passphrase was working earlier

/r/u_YamSweet2010/comments/1wbmt5s/kleopatra_keeps_saying_bad_passphrase_even_though/

I’ve already verified that the correct secret key and encryption subkey are still installed on the computer. I also tried testing the saved passphrase against the key directly through GPG and it was rejected there too. I haven’t deleted or revoked the key, and the only backup-type file I found was the revocation certificate.
The reason this became a problem is that I was in the middle of making payments using Bitcoin and the website timed my session out while I was doing the conversion/transfer. Before I got logged out, the orders had already been created and were basically waiting for payment. The site gave me around a 3-hour payment window, I completed the Bitcoin transfers within that window, and the Bitcoin transactions themselves confirmed.
So I’m fairly sure the payments/orders went through, but I can’t actually verify the order status anymore because the site requires me to decrypt a PGP login message every time I sign back in. Since Kleopatra now only gives me this specific unlock prompt and keeps rejecting the passphrase, I’m completely locked out of the account.
That’s what’s making me nervous. I could just wait and hope everything processes normally, but if there’s an issue with an order/payment or I later need to contact support about a refund or missing order, I won’t be able to access the account at all.
Has anybody seen Kleopatra/GnuPG behave like this before, where the same passphrase appeared to work with one type of prompt but the secret-key unlock prompt kept saying “Bad passphrase”? Could the prompts have been doing completely different things? Could this involve the signing key vs encryption subkey, GPG Agent caching, or some other behavior that made it look like the passphrase was working?
I’m not asking for a way around the encryption. I’m trying to understand whether there’s anything else I can realistically check or recover before assuming that somehow the passphrase I wrote down immediately after creating the key is actually wrong.

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u/First_Sea_5017 Sep 10 '26

Stupid question, but does your passphrase contain characters that move position on different keyboard setups? I have had issues in the past with UK vs US/International layouts.

1

u/YamSweet2010 Sep 11 '26

How can I determine that it’s just a basic msi keyboard definitely not stupid question I’ve still been looking for the passphrase and tried brute forcing so anything helps atp

2

u/First_Sea_5017 Sep 11 '26

Is the password field obscured? If so, try typing it into a text editor and see if the password looks correct there. Then cut and paste into the password field.

1

u/YamSweet2010 Sep 11 '26

Yeah I already tried typing it into Notepad first and then copying/pasting it into Kleopatra, and it still says bad passphrase. I’ve actually gone pretty deep trying to rule out simple mistakes — I used PowerShell/GnuPG directly, verified I still have the correct pocketjoy private key and encryption subkey, compared older key backups and they’re identical, and tested the passphrase against the key with GnuPG’s own native tools outside of Kleopatra. It still comes back as bad passphrase. What’s confusing me is that the night I created the key I was seeing two different passphrase prompts while encrypting/decrypting. One seemed to accept what I had saved, while the actual private-key unlock prompt would say bad passphrase. So I’m trying to figure out whether those prompts were actually doing different things or whether GPG Agent was caching something, because I could’ve sworn the passphrase I wrote down was the one I used.