Importing keys into GnuPG 2.2 series

[Daniel Kahn Gillmor]

I'm confused by this e-mail, hopefully the notes and questions below can
start to un-confuse it a bit.

On Thu 2018-12-13 13:40:56 -0900, justina colmena via Gnupg-users wrote:
> OpenKeychain on my smartphone is able to verify the attached
> signatures .gpg, but not the detached .sig files.

This appears to be a question about OpenKeychain verifying signatures,
which has nothing to do with passphrases.  it might be better asked in
an OpenKeychain forum, as i don't know what user interface OpenKeychain
expects for dealing with detached signatures.

> For some reason I cannot get GnuPG 2.2.11 to recognize the passphrase
> for the secret key, which I am only able to set, use, or change in
> GnuPG 1.4.23.

GnuPG 1.4.23 and 2.2.11 do not really interoperate well, when sharing
the same homedir. I recommend that you choose one and stick with it.
2.2.11 is the better choice.

> MAIN QUESTION: Is this a pinentry-curses problem with the tty over
> ssh, or is it an actual key incompatibility issue?

you haven't described what action you're doing that makes you think that
you need a passphrase in the first place, or how you are connected to
your computer in such a way that "tty over ssh" is a meaningful
question.  please show more of what you're doing!

> If for some reason the key is not actually compatible with GnuPG 2,
> then shouldn't I just generate a new key in GnuPG 2, and then sign it
> with my old key in GnuPG 1 and also import it back into the
> OpenKeychain app if I want to use it on my phone?

this sounds like a very complicated route to take, and it results in you
having multiple outstanding keys, which is likely to confuse some of the
people you communicate with.  i'd try to keep it simpler if possible.

regards,

       --dkg