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The pretty permalink built-in is said to be /:categories/:year/:month/:day/:title/, but when putting that in instead of pretty it generates different results.
With pretty: /2014/02/20/a-post-test-or-welcome/index.html
With /:categories/:year/:month/:day/:title/: /2014/02/20/a-post-test-or-welcome/
It seems that pretty actually appends a index.html to the URL. This is actually documented, but it makes no sense for the "same" style to not do the same. Looking at the actual _site generated by the long version, there is an index.html for each post, but because using a slash defaults to the index.html this works. However, when using pretty, the resulting page.url has an index.html instead of not having one.
Edit: One last thing, using pretty messes up the entire site, organizing my non-post pages into index.html files under their respective folders.
I can’t reproduce it.
The original problem with pretty seems to have disappeared. But the second one remains. My default about.html is at http://techshroom.github.io/about.html. But with pretty on instead of my copy+paste of pretty, it generates as http://techshroom.github.io/about/, which I don't want. Fork https://github.com/TechShroom/TechShroom.github.io/ to test it.
Looks like a dupe for #2399
Yes, it does.