If the "autosecure" option of GpgOL is set to "on", the decision to not secure because there is no suitable certificate available for one recipient is sometimes wrong.

In a case reported by a customer the log showed that the decision was made based on an expired key for one recipient address despite a valid certificate was available, too.
Reproduced with one disabled and one valid certificate.
The mail was not automatically secured when sending in spite of the available valid certificate. Im the case of manually choosing "Secure", the mail was encrypted to the expected certificate, though.

Corresponding gpgol + gpgme log file created, sender was the Edward-testing account, receiver Teds.