Ssh key sync problems between linux server and windows server

[Roberto Sabelli]

Hi everyone, I have this problem that I can't solve:

I have a linux server (Red Hat Enterprise Linux 6 64bit) and a Windows
server (Windows Server 2016 Datacenter).
CYGWIN v. 1.5.22 is installed on the Windows server.
If I make an SSH connection between the Linux server and the Windows server
and I try to copy a file from the linux machine to the windows machine
everything works. If I restart the Windows server and try to connect and to
copy a file again I get this error:

*+ ssh username@linuxserver '[ -d /cygdrive/c/pippo/pluto/gio/DS ]’*
*+ '[' 66 -eq 0 ']’*
*+ echo '[ERROR] Folder /cygdrive/c/pippo/pluto/gio/DS doesn't exist’*

The problem persists for some time (it can be minutes or hours) then as if
by magic it resolves itself and everything works again.

It seems that the ssh session opens correctly but cannot find the path in
the Windows machine but I assure you it exists.

This happens every time the Windows server restarts or even just the CYGWIN
sshd service.

Do you have any ideas to help me?

Thank you all for the support.

Roberto