Hi,

Why not set

pinentry-program 
/usr/local/MacGPG2/libexec/pinentry-mac.app/Contents/MacOS/pinentry-mac

in gpg-agent.conf?

In both of your files there are things with ‘pinentry loopback’.  I don’t know 
what it is, but maybe the first step would be to have a pinentry program 
actually pop-up?  I don’t know what loopback refers to, but I would start to 
investigate there.

Good luck,
Thomas

On 5 Jan 2021, at 14:56, Sebastian Hagedorn wrote:

> Thanks. I went one a side quest for a while, because your public key couldn’t 
> be loaded. Somehow the Let’s Encrypted certificate for 
> hkps://keys.openpgp.org wasn’t trusted. I switched to 
> eu.pool.sks-keyservers.net, and now that part is working, at least.
>
> To answer your question: yes, gpg-agent is running:
>
>   505  1633     1   0 11:15am ??         0:00.30 gpg-agent --homedir 
> /Users/hgd/.gnupg --use-standard-socket --daemon
>
> The version that’s running is from MacGPG. I also have a separate 
> installation from Homebrew, but that’s not being used. Perhaps we could 
> compare configuration files?
>
> gpg-agent.conf:
>
> default-cache-ttl 300
> max-cache-ttl 999999
> #pinentry-program
> allow-loopback-pinentry
>
> gpg.conf:
>
> armor
> #openpgp
> default-key haged...@spinfo.uni-koeln.de
> encrypt-to 09C25485
> force-mdc
> #compress-algo 1
> #no-secmem-warning
> trust-model direct
> #keyserver hkp://wwwkeys.de.pgp.net
> keyserver-options include-subkeys no-include-revoked timeout=5
> charset utf8
> utf8-strings
> group uk...@uni-koeln.de=4D105B45 C46E14A6
>
> group BUDDY=
> emit-version
> auto-key-locate keyserver
> auto-key-retrieve
> use-agent
> pinentry-mode loopback
>
> To be honest, some of these options are 20 years old, and I don’t even 
> remember what there were for :D
>
> Cheers,
> Sebastian
>
> On 5 Jan 2021, at 13:05, Thomas Kahle wrote:
>
>> On 5 Jan 2021, at 12:23, Sebastian Hagedorn wrote:
>>
>>> Possible, but IMO that’s not really a solution. Every other mail 
>>> application I have used had a method for requesting and/or storing the 
>>> passphrase. It’s also stored in my keychain. Can somebody confirm if that 
>>> is expected behaviour with a protected key?
>>
>> I use encrypted pgp keys whose passphrases are stored in keychain and it 
>> works completely transparently.
>>
>> When I switched from Thunderbird to Mailmate it just worked out of the box.  
>> Have you configured gig-agent?  Is it running?
>>
>> What’s the output of `ps -ef | grep gpg-agent` ?
>>
>> Cheers,
>> Thomas
>>
>>
>>
>>>
>>> On 5 Jan 2021, at 12:11, Alexandre Takacs wrote:
>>>
>>>> It would seems that your key I password protected and PGP is working in a 
>>>> batch mode not allowing it to request said pass.
>>>>
>>>> Can you try with a non protected key (as a test to validate the above) ?
>>>>
>>>> On 5 Jan 2021, at 10:56, Sebastian Hagedorn wrote:
>>>>
>>>>> gpg: Sorry, we are in batchmode - can't get input
>>>>>
>>>>> I have a suspicion that is caused by something in my gpg settings, but I 
>>>>> don’t see anything obvious.
>>>>> Ideas?
>>>> _______________________________________________
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>>>> https://lists.freron.com/listinfo/mailmate
>>> _______________________________________________
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>>> mailmate@lists.freron.com
>>> https://lists.freron.com/listinfo/mailmate
>>
>> --
>> Thomas Kahle
>> https://www.thomas-kahle.de
>
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--
Thomas Kahle
https://www.thomas-kahle.de

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