When you face this kinds of problem in Windows, you could check below two things in registry. 1. HKEY_CLASSES_ROOT\Python.File 2. HKEY_CLASSES_ROOT\*\shell First, HKEY_CLASSES_ROOT\Python.File 1> Open regedit 2> Go to 'HKEY_CLASSES_ROOT\Python.File\shell\Edit with IDLE\command', if it does not exist create it by click right mouse button. 3> Adjust the value of key; "[PYTHONPATH]\pythonw.exe" "[PYTHONPATH]\Lib\idlelib\idle.pyw" -e "%1" 4> And then go to 'HKEY_CLASSES_ROOT\Python.NoConFile\shell\Edit with IDLE\command'. 5> Adjust the value of key; "[PYTHONPATH]\pythonw.exe" "[PYTHONPATH]\Lib\idlelib\idle.pyw" -e "%1" Second, HKEY_CLASSES_ROOT\*\shell 1> Open regedit 2> Go to 'HKEY_CLASSES_ROOT\*\shell' and create a key below with name of 'command'. 3> Adjust the value of key; "[PYTHONPATH]\pythonw.exe"