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A problem we're starting to see on distutils-sig is folks trying to type pip commands into the Python REPL rather than their system shell, and getting cryptic syntax errors back:
>>> pip install requests
 File "<stdin>", line 1
 pip install requests
 ^
SyntaxError: invalid syntax
>>> python -m pip install requests
 File "<stdin>", line 1
 python -m pip install requests
 ^
SyntaxError: invalid syntax
This may be amenable to a similar solution to the one we used to give a custom error message for "print ":
>>> print foo
 File "<stdin>", line 1
 print foo
 ^
SyntaxError: Missing parentheses in call to 'print'
That code currently checks for "print " and "exec ", so it would be a matter of adding another special case that looked for "pip install " appearing anywhere in the string that's failing to compile (it can't be limited to the start as it may be an attempt to invoke pip via "-m")