@m.eik Could you please enable debug option for gpg-agent and get the log output for the crash?

I fixed the problem (which I identified above) in gniibe/t7759 branch. There might be other causes/problems for the particular symptom, so, I don't know the fix resolves the symptom or not.

Thank you for the report.

Similar situation could happen with gpgsm + gpg-agent, when gpg-agent is invoked by gpgsm.
(1) No gpg-agent.
(2) In gpgme, by engine-gpgsm, gpgsm is invoked with --logger.
(3) In gpgsm_keylist, it makes sure gpg-agent is available by GETINFO agent-check, using gpgsm_assuan_simple_command.
(4) In the server side, it tries to connect gpg-agent, invokes gpg-agent, and connect to the agent again.
(5) On Windows, it may takes time to invoke gpg-agent. And it may try to connect multiple times. Each trial may generate debug messages.
(6) When it takes too much time, the debug messages are too much. It may fill the pipe.
(7) And it blocks at log_string in my_libassuan_log_handler.
(8) ... it hangs.

Hypothetical scenario (gpgsm --server + dirmngr):
(0) It may hang when much debug messages are generated by libassuan to the pipe of --logger (diag_cb).
(1) In gpgme, by engine-gpgsm, gpgsm is invoked with --logger.
(2) If it's the case of standard gpgme interactions which uses gpgsm_io_event, no problem. Because the data on diag_cb is consumed well.
(3) In case of gpgsm_encrypt (or other commands), it uses gpgsm_assuan_simple_command which does not consume the data on diag_cb pipe at all.
(4) In particular, in set_recipients, gpgsm_assuan_simple_command is called by the number of recipients.
(5) IIUC, in the server side, dirmngr is used by the call chain of:

• gpgsm_add_to_certlist
• gpgsm_validate_chain...
• gpgsm_dirmngr_isvalid

(6) In gpgsm_dirmngr_isvalid function, libassuan is used as client side, it generates debug messages.
(7) When there are many recipients, the debug message may be big enough to fill the pipe.
(8) When pipe is filled, it blocks by log_string in my_libassuan_log_handler, waiting the data in pipe is consumed.
(9) ... it hangs.