While setting up my new site, I was testing out the nav menu, however /presentations/ and /documents/ looped without an end. It should be noted that directories with the same name existed as the page slugs (permalinks). So after changing the .htaccess to include the rewrite even if a directory exists.
#RewriteCond %{REQUEST_FILENAME} !-d
After inspecting the headers being sent I saw:
Location: presentations/ Location: presentations Location: presentations/ Location: presentations Location: presentations/ Location: presentations Location: presentations/ Location: presentations Location: presentations/ Location: presentations Location: presentations/ Location: presentations
So after pages of irreverent Google results I came across a solution.
Solution: Add a trailing slash at the end of the permalink.
And so the problem was solved. 