Jun 16 2017
ImageTaggingBot's most recent encounter with this issue is from June 6, for https://en.wikipedia.org/wiki/File:Tennis_A_Team_1926.jpg. Since the bot has been averaging only a few reports of this a month, any fixes since then won't be obvious yet.
Dec 22 2015
Not fixed in -wmf9: https://en.wikipedia.org/wiki/File:JoJo_-_LOVEJO2_(Official_EP_Cover).png (query https://en.wikipedia.org/w/api.php?action=query&format=xml&prop=templates|revisions&titles=File:JoJo_-_LOVEJO2_(Official_EP_Cover).png&tllimit=500&meta=userinfo&rvprop=content&uiprop=hasmsg&redirects=1), uploaded yesterday morning, still has problems.
Dec 13 2015
This doesn't appear to have been fixed in -wmf8. ImageTaggingBot reported errors on https://en.wikipedia.org/wiki/File:Elitch_Gardens_Logo.png (query https://en.wikipedia.org/w/api.php?action=query&format=xml&titles=File:Elitch_Gardens_Logo.png&redirects=1&meta=userinfo&tllimit=500&prop=templates|revisions&uiprop=hasmsg&rvprop=content) and https://en.wikipedia.org/wiki/File:Charity_Standish.jpeg (which has since been edited), both of which were uploaded earlier today.
Nov 1 2015
Server response headers from https://en.wikipedia.org/w/api.php?action=query&format=xml&titles=File:Kerbisher2.gif&tllimit=500&meta=userinfo&rvprop=content&prop=templates|revisions&redirects=1&uiprop=hasmsg
Oct 31 2015
Like I said, it's intermittent. ImageTaggingBot appears to encounter this once every thousand requests or so.