Congratusorry 

A word that simultaneously expresses both joy and condolence for the fortunes of another, "congratusorry" should be directed towards an individual when they suffer disappointing results from a situation that typically concludes with a positive outcome. A question mark after congratusorry isn't entirely necessary, but can prove helpful in ambiguous situations. (Also see "seizing defeat from the jaws of victory".)

Jim: My wife just had a baby.
Bob: That's wonderful...
Jim: It wasn't mine.
Bob: Oh... congratusorry?

Congratusorry by Le_Sigh December 30, 2008

Congratsory 

A term to be used in a situation when you do not know whether to Congratulate OR Apologize to the other person. It is often followed by a question mark or stated as a question because you do not know whether its a good or a bad thing

Ex:

Female Friend 1: I just found out I'm pregnant.
Female Friend 2: Congratsory??

Congratsory by Fe Dubrovna February 5, 2010