So I picked up Where's Waldo when it was on sale for $3(ish) on Games for Windows Live.  My in-laws were in town and my consoles were pretty much off limits. I figured play through a mindless GFW game and get some sweet achievements while I was at it.  This seemed to to work for the most part, but the achievements for beating the game (both difficulties) and the 180 star achievement are glitched.  
 
I was able to get the achievements for beating the game on normal and kid difficulty by erasing the previously completed games and playing through again.  Now all that's left is the 180 stars achievement.  I have played through the game on normal many many times and every time I'll finish the game with 180 stars.  The game goes to the next screen, it seems to slow down while the achievement begins to pop, and the achievement details populate.  The achievement will stay on my profile for about 5 seconds and then the achievement vanishes.
 
I have tried the trick about saving my game before the last world and reloading, but the same thing happens.  I tried the suggestions about getting other achievements in GFW titles and then trying the Waldo game to see if the achievement sticks.  I got achievements in Tinker and Batman, but the last Waldo achievement still is crap. 
 
I emailed the Publisher and they say it's an issue with the Games for Windows service.  I email them and the moderators on the forums don't have any suggestion.  If anyone on Giant Bomb has any suggestions I would take the suggestion.