u/Any_Device6567

I have a YubiKey Nano (5.7.4) set up to sign, encrypt and authenticate documents which works fine. To set up PGP with my Yubikeys I used Gpg4win-5.0.2/ Kleopatra. I am using TB 150.0.2 (64-bit) with windows 11 pro.

gpg --list-secret-keys shows ssb> (keys are on the card)

Every time I try and send an email after selecting OpenPGP -->Digitally Sign I get the error message "Sending of the message failed."

OpenPGP Key Manager ->Key Properties->Your Acceptance: Yes, I’ve verified in person this key has the correct fingerprint.

OpenPGP Key Manager -> Key Properties-> Structure: It has the same structure as the Kleopatra screen grab.

When I send the message TB thinks for a couple of seconds then I get the error message. I never get the Pinentry to unlock the key so its like TB cant find the Yubikey.

In Config Editor tried:
mail.openpgp.alternative_gpg_path C:\Program Files\GnuPG\bin\gpg.exe
mail.openpgp.load_untested_gpgme_version 45
allow_external_gnupg is true

Those updates to the Config Editor made no changes, "Sending of the message failed.".

I have noticed if I go into Account Settings ->End To End Encryption-> Advanced Settings and deselect everything then the email will be sent without an error.

If I select "Attach my public key when adding an OpenPGP digital signature" or "Send OpenPGP public key(s) in the email headers for compatibility with Autocrypt"

I get "Sending of the message failed."

I have also tried running TB as administrator.

Am I missing something obvious?

Thanks!

I was having issues with FB's implementation of Passkeys:

https://www.reddit.com/r/facebook/comments/1ruabsu/when_is_passkey_implementation_going_to_be_fixed/

Once a month I would go in and see if it had been resolved. This is resolved, wooo hooo! Thanks!

I am able to remove the orphaned passkey and added a passkey to my yubikey and password manager.

I noticed though when I added my Yubikey FB does not allow me to tag which Yubikey is my Primary, Secondary or Backup Key. If I lose or break a key I have no way of knowing which Yubikey I need to remove/replace because FB is naming my YubiKey's "Unknown". Please Allow labels for each passkey registered.

Additionally, I have Registered a passkey with my password manager, nano yubikey and a backup yubikey. Looking at the display of passkeys registered FB only shows two passkeys registered when in fact there are three keys registered.

I have tested and all three registered keys work but only two keys are shown in FB. I have two more yubikeys I would like to register but am hesitant to register them since they dont show up in FB. How would I ever remove them if a key was broken or lost? Please display all registered passkeys. Currently there appears to be a limit of only two keys being displayed. I have three passkeys registered, they all work, but only two keys are shown in the add/remove passkey workflow.

Thanks!

Cannot get Thunderbird to use External GnuPG Key (YubiKey)