The Portuguese and Galician pluperfect is unique in Romance. Rather than developing a generalized compound pluperfect structure early, as did French and Spanish (e.g., Fr. J’avais chanté ‘I had sung’) the Latin pluperfect indicative survived with its original semantics into the 20th century (Lat. cantāveram > Port. cantara ‘I had sung’). This paper presents a thorough description of the development of the Portuguese pluperfect and then proposes an explanation as to why it diverges from the standard Romance pattern.Amaral and Howe (2009) attribute the unique iterative semantics of the Portuguese compound past to auxiliary ter ‘to have’ generalization. Similarly, this paper proposes that ter selection is also behind the unique pluperfect situation. Specifically, when ter was generalized over haver in the 16th century, the resultative/stative interpretation of the compound pluperfect verb form was preferred. This delayed a grammaticalization process that allowed the compound pluperfect to gain an eventive interpretation and to more freely alternate with—and eventually supplant—the synthetic pluperfect from Latin.Using empirical data from the Corpus do Português (Davies & Ferreira, 2006), this work describes the development of the Portuguese pluperfect and concludes that the generalization of auxiliary ter is the primary reason for the prolonged survival of the Latin synthetic pluperfect form.