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There should be an easy way to check a reST long_description on one's local machine before uploading to PyPI. The check should use the same rules that PyPI uses, so that passing the check locally ensures that PyPI will convert the description to HTML successfully.
Issue 15231 is related and focuses on the current documentation. See that issue for some background and ideas.
Also see the corresponding issue filed on the PyPI tracker:
http://sourceforge.net/tracker/?func=detail&aid=3539253&group_id=66150&atid=513503 

This easy way exists: "pysetup run check" checks the rst syntax; retitling.
Basically it’s a matter of using the same settings (no file inclusion, etc.) as PyPI and checking the URI schemes.
One maintenance issue is the possible discrepancy between PyPI’s checks and distutils2’s; if the PyPI maintainers agree to announce all changes to catalog-sig it could work (just like for classifiers).

With regard to the maintenance issue, what about the idea of aiming for PyPI to include that logic in a separately packaged module? Then there would be no need to cut and paste -- just include the right version.
If that were done, depending on how the pysetup change is done, users might be able to use PyPI's latest version even if pysetup was out of synch and hadn't been updated yet.

> One maintenance issue is the possible discrepancy between PyPI’s 
> checks and distutils2’s; if the PyPI maintainers agree to announce 
> all changes to catalog-sig it could work (just like for classifiers).
We can certainly try to remember, but I expect this is prone to fail:
the next change may well be five years from now, at which point nobody
remembers that distutils2 also has such a check.

Reclassifying as distutils feature request.

Éric is not quite correct: I currently have a package where "python setup.py check" does not show any error, but PyPI still refuses to format my long description. Likewise "python setup.py --long-description | rst2html-2.7.py > /dev/null" also does not reveal any errors or warnings, so I am at a completely loss as to why PyPI refuses to format my documentation.

This issue is 7 years old: it's far from being "newcomer friendly", I remove the "Easy" label.

Hi Victor,
This is the 3rd issue in a row I found in the "Easy issues" list where you added a comment saying
> I remove the "Easy" label
Why are can I still find these issues in the "Easy issues" list?
Do you mean that you already removed the "Easy" label or that you plan to remove it?

@Giovanni ,
If you look closely, the issue still has the easy issue label that is why you still see it in the "Easy issues" list. Which means he has not removed the label yet.

> Why are can I still find these issues in the "Easy issues" list?
My bad... I only added a comment but forgot to remove the easy keyword. It's now removed ;-)

Distutils is now deprecated (see PEP 632) and all tagged issues are being closed. From now until removal, only release blocking issues will be considered for distutils.
If this issue does not relate to distutils, please remove the component and reopen it. If you believe it still requires a fix, most likely the issue should be re-reported at https://github.com/pypa/setuptools