Communication is a huge challenge for oesophageal speakers, be it for interactions with fellow humans or with digital voice assistants. We aim to quantify these communication challenges (both human–human and human–machine interactions) by measuring intelligibility and Listening Effort (LE) of Oesophageal Speech (OS) in comparison to Healthy Laryngeal Speech (HS). We conducted two listening tests (one web-based, the other in laboratory settings) to collect these measurements. Participants performed a sentence recognition and LE rating task in each test. Intelligibility, calculated as Word Error Rate, showed significant correlation with self-reported LE ratings. Speaker type (healthy or oesophageal) had a major effect on intelligibility and effort. More LE was reported for OS compared to HS even when OS intelligibility was close to HS. Listeners familiar with OS reported less effort when listening to OS compared to nonfamiliar listeners. However, such advantage of familiarity was not observed for intelligibility. Automatic speech recognition scores were higher for OS compared to HS