In this paper we pursue the hypothesis that the distribution of article omission specifically is constrained by principles of Information Theory (Shannon 1948). In particular, Information Theory predicts a stronger preference for article omission before nouns which are relatively unpredictable in context of the preceding words. We investigated article omission in German newspaper headlines with a corpus and acceptability rating study. Both support our hypothesis: Articles are inserted more often before unpredictable nouns and subjects perceive article omission before predictable nouns as more well-formed than before unpredictable ones. This suggests that information theoretic principles constrain the distribution of article omission in headlines.