This chapter investigates the perceived adequacy of the discourse of gratitude. It reports on a study in which questionnaires were administered to native speakers of English with experience as university lecturers. These questionnaires explored the envisaged impact on the addressee of foreign language learners’ written speech acts of thanking, the relevance of given textual-strategic features to the communicative effectiveness of speech acts of thanking, and the texts’ linguistic and textual problem areas relatable to the writers’ L1 background. The English lecturers expressed their likely cognitive, emotional, and behavioural responses to the learners’ writing, and indicated that they attributed importance to, and held the writers responsible for, logic and coherence, consideration of the addressee’s circumstances, and reader-friendliness. They identified two types of inadequacies: inaccuracy (e.g., deviations from linguistic norms), and inappropriateness (e.g., incongruity between text and co(n)text). The argument is put forward that language learners could enhance their interactional skills by adopting an other-oriented communicative perspective on their discourse, considering the interlocutor’s interactional rights, expectations, and foreseeable reactions.