It looks like this is a bug in pyreadlines as suggested by eryksun, but for a different reason.

Even though the Caps Lock + Shift combination is recognized correctly (as lower case), the logic in the pyreadlines module forces it to upper case.

See lines 44-45 and 72-75 in [1].

You should be able to verify this by launching with the -S option, disabling the auto import of the site module.  (You'll need to import sys; sys.exit(), or Ctrl+Break to exit the interpreter -- exit() won't be defined.)

Given that pyreadlines looks to be somewhat of a mess and since you don't actually need pyreadlines to run ipython[2], you might consider uninstalling it (Alternatively, removing the "or shift" part of the referenced conditions will fix your specific issue).

If you're only looking for windows terminal coloring, colorama[3] is being used by the pip maintainers with apparent success.

In any case, it doesn't look to be an appropriate bug for this tracker -- maybe the pyreadlines github?


[1] https://github.com/pyreadline/pyreadline/blob/master/pyreadline/keysyms/common.py
[2] http://mail.scipy.org/pipermail/ipython-dev/2013-November/012623.html
[3] https://pypi.python.org/pypi/colorama