Health systems are integrating interventions to assist patients with food insecurity; however, people need varying levels of support. Rather than using a single intervention, adaptively providing interventions may be a more effective approach. The authors conducted a pilot, sequential, multiple-assignment randomized trial to determine the feasibility of an adaptive food insecurity intervention. Adults with uncontrolled hypertension who reported food insecurity were randomized to one of two interventions for 3 months in Stage 1: information about community resources or community health worker (CHW) support. Participants who did not have ≥10 mmHg improvement in systolic blood pressure at 3 months were re-randomized to CHW support or the delivery of medically tailored meals (MTM) in Stage 2 for an additional 3 months. We evaluated the proportion who enrolled, completed follow-up, and had an improvement in blood pressure. Sixty of 61 (98.3%) eligible patients enrolled. Four withdrew, 46 of 56 (82.1%) completed the 3-month follow-up, and 40 of 56 (71.4%) completed the 6-month follow-up. Of 27 randomized to resource information, 15 (55.6%) did not have ≥10 mmHg improvement and were re-randomized. Of 29 randomized to CHW support, 14 (48.3%) were re-randomized. The adaptive intervention that provided CHW support in Stage 1 and additional CHW support in Stage 2 resulted in 46.7% of participants with ≥10 mmHg improvement in systolic blood pressure at 6 months. The adaptive intervention that provided CHW support in Stage 1 and MTM in Stage 2 resulted in 66.7% of participants with ≥10 mmHg improvement. This study found that an adaptive food insecurity intervention was feasible to utilize.