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The short answer for future viewers of this question is that PuTTY 0.71 at least and possibly other versions require adding -P 22 to the command line even in the default case, so it's necessary to set SSH Port to Use Specified Port and 22. Otherwise, Wing does not add a -P to the command line, which is done because it's possible to configure the port outside of Wing also, through putty.exe or in .ssh/config if using OpenSSH. The UI will be changed in Wing 7.2.8.1+ to clarify that default doesn't necessarily mean port 22.