eryksun added the comment:

Using a relative target in the link isn't the problem for me here. (See issue 
13702 for another problem with relative links.) I'm in the same boat as 
commenter weberc2. Same symptom; apparently a different problem.

I'm using an absolute path for the target:

C:\Program Files\Python\Scripts>mklink python2.7.exe "C:\Program 
Files\Python\Python27\python.exe"
symbolic link created for python2.7.exe <<===>> C:\Program 
Files\Python\Python27\python.exe

(Mirror the --user layout in %AppData%.)

This works fine from cmd, but not Explorer. Anyway, the link would be added to 
support shell scripts that use shebangs for environments such as MSYS, so 
executing with Explorer isn't the goal anyway. The shortcut in the start menu 
would target python.exe, not the symbolic/hard link.

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<http://bugs.python.org/issue21506>
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