This study investigates prosodic challenges faced by Italian learners of L2 Mandarin at varying proficiency levels, focusing on the production of the falling tone (T4) within disyllabic phrases that convey multiple prosodic meanings across communicative contexts. Participants’ Mandarin tone proficiency in isolation was first assessed through identification and production tasks. The main experiment involved paired readings of short dialogues eliciting the production of disyllabic target phrases in multiple tone combinations across two sentence types (statement and echo question), with contrastive prosodic focus on syllable 1 (Syl1) or syllable 2 (Syl2). The experiment included 130 pseudo-randomized dialogues (64 target phrases, 70 fillers). The results showed distinct F0 contour patterns for T4 on Syl1 and Syl2. On Syl1, sentence type affected the F0 contour, with a syllable-final rise in statements, indicating difficulty in maintaining the expected T4 fall, due to both tonal and intonational reasons. On Syl2, F0 varied significantly by sentence type, with questions displaying a prominent syllable-final rise, primarily influenced by intonational demands rather than by the production of T4 itself. These findings suggest the presence of prosodic difficulties in tone production that differ from those observed in isolated tone production. Preliminary results indicate that Italian learners prioritize intonation patterns over lexical tone contours, diverging from the prosodic strategies of native Mandarin speakers and compromising tone production accuracy that they may otherwise achieve in isolation. Proficiency emerged as a stronger predictor of tone and intonation accuracy than variables such as University Year and Musicality.