Paul Ganssle <p.gans...@gmail.com> added the comment:

> In short, a+b can overflow, but a-b cannot?

I think it's more that by always checking the elapsed time against `now() - 
starttime`, you never need to represent the time at which the timeout should 
happen - which may be so far in the future that it causes a signed overflow.

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Python tracker <rep...@bugs.python.org>
<https://bugs.python.org/issue33632>
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