The problem may be related to the potentially incompatible changes introduced in OpenSSH 6.7  (included in Copssh 5 and higher) to remove unsafe algorithms.

• I am fond of fancy and short names :-))

   

  Cygwin + OPENSSH is a qualified guess !!

• Some recommendations (not all of them can be applicable in your case, no sorting by importance):
   

• Dependent on software or configuration issues on your PC, copssh service may sometimes not start properly. The problem can be a service, a device helper, anti virus, firewall and so on, interferencing operations of the copssh service.

   A possible solution is to delay the service startup until the problem services are started successfully. You can use the procedure below to make copssh service dependent on MyService:

   

• Sometimes it may be necessary to see directly how the openssh daemon reacts to startup or connection requests, to be able to locate daemon-related problems.