In 2021, the National Guideline Alliance for the Royal College of Obstetricians and Gynaecologists reviewed the body of evidence, including two meta-analyses, implicating supine sleeping position as a risk factor for growth restriction and stillbirth. While they concluded that pregnant people should be advised to avoid going to sleep on their back after 28 weeks’ gestation, their main critique of the evidence was that, to date, all studies were retrospective and sleeping position was not objectively measured. As such, the Alliance noted that it would not be possible to prospectively study the associations between sleeping position and adverse pregnancy outcomes. Our aim was to demonstrate the feasibility of building a vision-based model for automated and accurate detection and quantification of sleeping position throughout the third trimester–a model with the eventual goal to be developed further and used by researchers as a tool to enable them to either confirm or disprove the aforementioned associations. We completed a Canada-wide, cross-sectional study in 24 participants in the third trimester. Infrared videos of eleven simulated sleeping positions unique to pregnancy and a sitting position both with and without bed sheets covering the body were prospectively collected. We extracted 152,618 images from 48 videos, semi-randomly down-sampled and annotated 5,970 of them, and fed them into a deep learning algorithm, which trained and validated six models via six-fold cross-validation. The performance of the models was evaluated using an unseen testing set. The models detected the twelve positions, with and without bed sheets covering the body, achieving an average precision of 0.72 and 0.83, respectively, and an average recall (“sensitivity”) of 0.67 and 0.76, respectively. For the supine class with and without bed sheets covering the body, the models achieved an average precision of 0.61 and 0.75, respectively, and an average recall of 0.74 and 0.81, respectively.