This article extends the work of Flajolet [Philippe Flajolet, 1987] on the relation between generating series and inherent ambiguity. We first propose an analytic criterion to prove the infinite inherent ambiguity of some context-free languages, and apply it to give a purely combinatorial proof of the infinite ambiguity of Shamir’s language. Then we show how Ginsburg and Ullian’s criterion on unambiguous bounded languages translates into a useful criterion on generating series, which generalises and simplifies the proof of the recent criterion of Makarov [Vladislav Makarov, 2021]. We then propose a new criterion based on generating series to prove the inherent ambiguity of languages with interlacing patterns, like {a^nb^ma^pb^q | n≠p or m≠q, with n,m,p,q ∈ ℕ^*}. We illustrate the applicability of these two criteria on many examples.