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If you activate the env from the command line and then start Wing from same command line, it inherits the environment unless it opens a project that overrides the default Python environment. An idea to prevent that if you had other projects open sometimes is to uncheck the Projects > Auto-reopen Last Project preference, so it always opens the default project, and leave that project configured so it doesn't specify a non-default Python. Then I think opening your file with 'wing' (or wing12 or whatever the executable is in your case; depends on OS and version of Wing) should open the file and have the right env if you run/debug it.