Mac GPG can't generate smartcard keys

Question

Mac OS X Catalina 10.15.7, Homebrew GPG 2.2.23, brand new Yubikey 5C Nano, homebrew pinentry-mac 0.9.4

% gpg --card-edit

Reader ...........: Yubico YubiKey OTP FIDO CCID
Application ID ...: D1234567890
Application type .: OpenPGP
Version ..........: 3.4
Manufacturer .....: Yubico
Serial number ....: 1234567890
Name of cardholder: Jamie Bliss
Language prefs ...: en
Salutation .......:
URL of public key : [not set]
Login data .......: [not set]
Signature PIN ....: not forced
Key attributes ...: ed25519 cv25519 ed25519
Max. PIN lengths .: 127 127 127
PIN retry counter : 3 3 3
Signature counter : 0
KDF setting ......: off
Signature key ....: [none]
Encryption key....: [none]
Authentication key: [none]
General key info..: [none]

gpg/card> admin
Admin commands are allowed

gpg/card> generate
Make off-card backup of encryption key? (Y/n) n
gpg: error checking the PIN: End of file

My gpg-agent.conf:

enable-ssh-support
pinentry-program /usr/local/bin/pinentry-mac
log-file /Users/jbliss/.gnupg/agent.log

Nothing useful in the log.

Answer 1

Had the same problem it looks like it's a bug in >=2.2.22 that the developers are aware of. See https://dev.gnupg.org/T5086