Hi,

that didn’t really help. With that setting I get:

gpg: invalid pinentry mode 
'/usr/local/MacGPG2/libexec/pinentry-mac.app/Contents/MacOS/pinentry-mac'

But it led me in the right direction. I commented out the pinentry-mode lines, 
and now it seems to be working! I get a warning that SHA-1 is used and this 
recommendation:

The hash function used for the message digest has been obsoleted due to 
security concerns. You should change your OpenPGP settings to use a stronger 
hash algorithm for the digest (such as SHA256).

Do you know off-hand how I can do that?

Thanks,
Sebastian

On 5 Jan 2021, at 17:26, Thomas Kahle wrote:

> 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 [email protected]
>> 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 [email protected]=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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>>>> _______________________________________________
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>>>> https://lists.freron.com/listinfo/mailmate
>>>
>>> --
>>> Thomas Kahle
>>> https://www.thomas-kahle.de
>>
>>> _______________________________________________
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>>> https://lists.freron.com/listinfo/mailmate
>
>> _______________________________________________
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>> [email protected]
>> https://lists.freron.com/listinfo/mailmate
>
> --
> Thomas Kahle
> https://www.thomas-kahle.de

> _______________________________________________
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