[MlMt] A MailMate hang many people may encounter…

[Bill Cole]

On 2025-12-13 at 15:15:22 UTC-0500 (Sat, 13 Dec 2025 20:15:22 +0000)
Henry Seiden <mailmate at lists.freron.com>
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
>> bill at scconsult.com or billcole at apache.org
>> (AKA @grumpybozo and many *@billmail.scconsult.com addresses)
>> Not Currently Available For Hire
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