On 2025-12-13 at 15:15:22 UTC-0500 (Sat, 13 Dec 2025 20:15:22 +0000)
Henry Seiden <[email protected]>
is rumored to have said:
Bill,
I haven’t yet had the issue with GPG Keys here. I don’t understand
whether you encountered the issue on incoming secured email or
outgoing email bearing your sender’s key signed (as a warning within
MM).
As I said, the problem was with a specific set of incoming messages from
the Apple Product Security mailing list, which they send out with every
set of system updates.
This happens entirely without trying to do anything other than view
incoming mail.
My use of GPG keys is quite limited to a few contacts that use them.
One such is Benny to whom I haven’t had occasion to email lately.
Another is his feedback account.
So even after latest MacOS update, haven’t seen the rotating of
(public facing?) keys or recognizing incoming signed email as an issue
for me… Yet! Thanks for the heads. Up, though.
The rotation of keys was by Apple; their PGP key for the mail in
question was rotated in August. I should add that this hang isn't
MailMate's fault. Calling gpg directly from a shell to verify any of the
relevant emails resulted in gpg spitting out a warning and hanging. This
is a plausible cause because apparently the MacPorts gnupg2 package was
updated on my machine in November, so this week's batch of Apple mail
was the first I got with this latest version of the gpg binary.
Respectfully,
Henry Seiden
- -
Techworks Pro Co.
E: info<at>techworkspro<dot>com
W: http://techworkspro.com
On 13 Dec 2025, at 14:46, Bill Cole wrote:
For the past few hours I've been pounding my head against a MailMate
hang which I'm likely not alone with.
The latest batch of Apple Product Security emails caused MailMate to
hang for me very reproducibly. I don't know the full explanation for
why, but it has something to do with the GPG signatures on them. They
recently rotated keys, so while I had many keys in my keychain for
them, they were all expired. This shouldn't cause a hang in itself.
The messages are structured as single plain text MIME objects
including the signature, encoded by quoted-printable. This shouldn't
cause a hang in itself.
I don't fully understand the hang. However, the fix was relatively
simple: remove all the old APS keys from my GPG keychain, quit GPG
Keychain, kill all of the orphaned gpg and gpg-agent processes you
may have from failed attempts to open the problem messageand the
process running /usr/local/MacGPG2/libexec/shutdown-gpg-agent (which
starts at login.) Go to https://support.apple.com/en-us/102148 and
copy the current key. Launch GPG Keychain, which will notice the key
in the clipboard (if you copied it right) and prompt you to import
it. Once the right key is in the keychain, MailMate has no problem
with the messages.
--
Bill Cole
[email protected] or [email protected]
(AKA @grumpybozo and many *@billmail.scconsult.com addresses)
Not Currently Available For Hire
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