Martin Panter added the comment:

Looking at the 2.7.11 code, I think it should fail properly at this line 
<https://hg.python.org/cpython/file/v2.7.11/Modules/stropmodule.c#l1113>, which 
checks if the change in size of all the replacements overflows. Is there a way 
to get a stack trace or similar on Windows?

Your video only shows the operation taking a long time or hanging as far as I 
can tell, not the Python program crashing. I would expect the call to raise 
MemoryError fairly quickly, after it has counted all 0xEAAA bytes to replace 
(but not actually replaced them).

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nosy: +martin.panter

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<http://bugs.python.org/issue26059>
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