Pregnancy brings numerous physiological and psychosocial changes and conditions, which can include gestational diabetes mellitus (GDM), and mental health conditions, including anxiety, and mood disorders such as depression. Food insecurity, or not having access to a diet that meets needs and preferences, may make management of pregnancy complications more challenging. I examined whether or not food insecurity was associated with a greater prevalence of mental health conditions, or GDM during pregnancy. I used the biocultural and syndemics approaches to the investigate the relationships among these conditions and to understand their interactions with the larger environment. The main questions are: (1) Does pregnancy increase the risk of developing or worsening food insecurity? (2) Are there positive associations between food insecurity during pregnancy and GDM as well as mental health conditions? (3) How does food insecurity impact the management of above-mentioned issues? (4) What are the experiences of individuals who have had GDM during pregnancy? To answer these questions, I undertook a mixed methods approach that involved quantitative analysis of the Canadian Community Health Survey, as well as a survey administered to pregnant people in the city of Hamilton. I also quantitatively analyzed pre-existing focus group transcripts and conducted one-on-one interviews with pregnant and postpartum people in Hamilton. This study found that there is a syndemic interaction between food insecurity, GDM, and mental health conditions in Canada. Analysis of focus group and interview transcripts provided further insight into the complex environments that shape risk for developing one, or more of these conditions during pregnancy. These results indicate how the pregnancy experience is impacted by a multitude of factors, which can lead to increasing complication risk. / Thesis / Master of Arts (MA)