This paper investigates apologies produced by Greek native speakers and English learners of Greek as a foreign language in two informal (-P, -D) and two formal situations (+P, +D). Drawing on data elicited by means of an assessment questionnaire, a DCT and the participants’ verbal reports, the study attempts to explore the extent to which the two groups differ in their contextual assessments of the apology situations under examination and in strategy use. The results indicated that the learners of the study differed significantly from the native speakers in regard to their assessments of the contextual parameters (power, distance, severity of offence) involved in each apology situation. Furthermore, significant quantitative and qualitative differences were attested in relation of the two groups’ preferences in strategy use when performing apologies in Greek. On the basis of these results it is argued, that these learners interlanguage apology behavior is influenced both by their native cultural values and (negative) politeness orientation, as well as from lack of adequate socio-pragmatic development resulting mainly from their foreign language learner status.