Military researchers utilize a five-item healthy eating score (HES-5) in the Global Assessment Tool (GAT) questionnaire to quickly assess the overall diet quality of military personnel. This study aimed to modify the HES-5 to improve its validity relative to the 2015 Healthy Eating Index (HEI-2015) in active duty military personnel (n = 333). A food frequency questionnaire was used to calculate HEI-2015 scores and to assess sugar-sweetened beverage (SSB) intake in 8-oz (SSB-8) and 12-oz servings. GAT nutrition questions were used to calculate HES-5 scores and capture breakfast and post-exercise recovery fueling snack (RFsnack) frequencies. Two scoring options were considered for the highest RFsnack category: "4" vs. "5" (RFsnack-5). Potential candidates were added alone and in combination to the HES-5 and compared to the HEI-2015 with a Pearson correlation coefficient. Scores with the highest correlations were compared via a z-score equation to identify the simplest modification to the HES-5. Correlations between HES-5 and HEI-2015 scores in total participants, males, and females were 0.41, 0.45 and 0.32, respectively. Correlations were most significantly improved in total participants by adding RFsnack-5, SSB-8, RFsnack-5 + SSB-8, and RFsnack-5 + SSB-8 + breakfast, though the addition of SSB-8 + RFsnack-5 performed best (r = 0.53). Future work should consider scoring mechanisms, serving sizes, and question wording.