This paper is a preliminary phonetic exploration of aspects of the well-known Italian sandhi phenomenon of Raddoppiamento sintattico (henceforth RS), which involves the gemination of word-initial consonants under certain conditions, eg dei [k]ani ‘some dogs’ but tre [kk]ani ‘three dogs’. It is often assumed that RS C-gemination is regular, but there is increasing evidence that it competes with other phenomena such as vowel lengthening. This paper first discusses results of our auditory study of RS contexts, which show that RS is far less frequent in spontaneous speech than is theoretically predicted. This paper then looks specifically at glottal stop insertion and creak in RS contexts, based on the results of an initial small-scale acoustic investigation. The first has controversially been reported as occurring in RS environments where it serves to block RS (Absalom & Hajek, 1997). In addition, glottal stops have also been claimed to provide a coda to short word-final stressed vowels outside of RS environments (Vayra, 1994). We discuss our unexpected finding that glottalization characterizes phrase boundaries in our spontaneous speech data, and the implications that this evidence may have for the phonetic and phonological description of Italian and for our understanding of RS.