Take for example the 'Gorilla' issue that Google encountered.
http://nyti.ms/1JlTBab [www.nytimes.com]
Then there was the issue with the bookmarks and suicide categories
http://bit.ly/1JFkmCr [productforums.google.com]
(This one isn't as big of a problem, as the frustration was probably more due to the compulsory usage of the new bookmarks, but it still shows some hazards of auto-categorization).
With social things, it can sometimes be very hard to solve a problem that works for 95% of the population, but doesn't piss off the remaining 5% (often with good justification). Unfortunately, detecting when you're in that situation in the first place is sometimes equivalent to the problem you're trying to solve.
Use simple statistics to identify trouble spots.