Purpose: To describe the performance of the pillow that participants usually slept on with respect to retiring and waking cervico-thoracic symptoms, pillow comfort, and sleep quality. Methods: Participants (n = 106) were systematically recruited for a field trial comparing their own pillow and five trial pillows. Participants provided daily retiring and waking symptom reports and sleep-quality and pillow-comfort ratings prospectively for 1 week on each pillow. Linear and logistic regression models were used to investigate the relationship between pillow use, age, gender, sleep quality, pillow comfort, and waking and temporal (overnight) symptom reports. Results: No waking symptoms were reported by 42.5% of participants on their own pillow. Regular waking symptoms, failure to relieve retiring symptoms, uncomfortable pillows, and/or poor-quality sleep were reported by over 50% of participants. All participants who reported poor sleep quality also reported poor pillow comfort. Pillow-comfort reports were not related to any waking symptom report; however, reports of poor sleep quality were significantly related to waking cervical stiffness (adjusted odds ratio [AOR] = 4.3 [Confidence Interval (CI): 1.3-15.6]) and scapula pain (AOR 1/4 6.1 [CI: 1.1-31.6]). Feather pillow users provided consistently low reports of pillow comfort and sleep quality. Conclusion: Many participants appear to have made poor pillow choices, as poor sleep quality, low pillow comfort, and waking symptoms were common. Further research is required to understand why people choose particular pillows to sleep on, as well as to identify the best fit between person and pillow to optimize sleep quality and reduce waking symptoms.