Added a comment: I have narrowed this problem down.

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+[[!comment format=mdwn
+ username="https://me.yahoo.com/zoredache#d4929"
+ nickname="Zoredache"
+ subject="I have narrowed this problem down."
+ date="2016-08-23T20:49:08Z"
+ content="""
+The attachments do not seem to get attached to the page, if the page has a space in the name.
+
+For comparability with a wiki I had imported content from I adjusted the `wiki_file_chars` to `wiki_file_chars: '-[:alnum:]+/._ '`.
+
+Attachments work work fine when being attached to a page that matches `'-[:alnum:]+/._'`, but if you have a space in the page name attachments fail.
+
+"""]]