We improved the logging in Windows as part of bug 3183. Unfortunately a bug snuck in an we aren't logging things properly when given a file descriptor rather than a file HANDLE on Windows.
Fixed in r27931 and some related logging improvements in r27932 and r27933.
This is a fuzzy bug description, what i can read out of the mentioned fixes the read from stdout/stderr wasn't correct and this would probably affect other processes and not only ssh ? However testing tlclient build 4109 on Windows 8, tlclient.log shows proper logging of sub processes including ssh.
Test by checking output during session (-d5) for example when tunnels are connected, check pulseaudio / printing.
Verified using build 4109 on Windows 8 and it works as expected. ssh logs when a pulseaudio client connects to a channel.
Reopen because of bug 4569 comment 18.
We need to clean up the Windows subprocess code to fix this. Moving to bug 4886 instead.