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I initially misunderstood where this was happening. From the log you sent in, I see it's in context of trying to connect to the remote host. This occurs on Windows if you are using OpenSSH and don't use an ssh key pair, or if you use an ssh key but don't use the ssh agent. In either case a password needs to be typed and OpenSSH is designed to refuse a password provided by anything but you actually typing it in on the command line.

There two possible solutions:

1) Change to using Wing's builtin SSH implementation or PuTTY. You can change to a different SSH implementation with the Remote Development > SSH Implementation preference in Wing.

2) Set up an SSH key pair and load that into ssh-agent.

See https://wingware.com/doc/proj/ssh-setup-details for details on using each SSH implementation. That includes also how to set up an SSH key pair in each case.