What is the reason for the BBG category $\mathcal{O}$ failing to be closed under extensions i.e which of the 3 axioms of $\mathcal{O}$ does not hold under taking extensions? 


Is there a prototype of a counterexample? 



BGG Category $\mathcal{O}$ is not closed under extension
You can usually extend two modules from $\mathcal{O}$ by a module which is not semisimple for the Cartan subalgebra (i.e. fails to be a weight module). See Exercise 3.1. in [J. E. Humphreys, Representations of semisimple Lie algebras in the BGG category $\mathcal{O}$. Graduate Studies in Mathematics, 94].


