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With remote shells and WSL, there is no reliable way for a host terminal to determine the shell's working directory. The same also applies when using GNU Screen and tmux.
Tabby allows shells to report their CWD using the OSC 1337 protocol, originally implemented by iTerm.
This allows following:
"Copy current path" context/tab menu item to work
SFTP panel to open in the shell's current directory
Same for WinSCP
To enable this, add following to your remote shell's profile file and restart the shell / re-login: