Purpose. To test an iPad-delivered multiple behavior tailored intervention (Healthy Pregnancy: Step by Step) for pregnant women that addresses smoking cessation, stress management, and fruit and vegetable consumption. Design. A randomized 2 x 5 factorial repeated measures design was employed with randomization on the individual level stratified on behavior risk. Women completed three sessions during pregnancy and two postpartum at postdelivery months 1 and 4. Setting. Women were recruited from six locations of federally funded health centers across three states. Subjects. Participants (N = 335) were English-and Spanish-speaking women at up to 18 weeks gestation. Intervention. The treatment group received three interactive sessions focused on two priority health behavior risks. The sessions offered individually tailored and stage-matched change strategies based on the transtheoretical model of behavior change. The usual care group received March of Dimes brochures. Measures. The primary outcome was the number of behavior risks. Stage of change and continuous measures for all behaviors also were assessed. Analysis. Data were analyzed across all time points using generalized estimating equations examining repeated measures effects. Results. Women in the treatment group reported significantly fewer risks than those in usual care at 1 month (.85 vs. 1.20, odds ratio [OR] = .70) and 4 months postpartum (.72 vs. .91, OR = .81). Conclusion. Healthy Pregnancy is an evidence-based and personalized program that assists pregnant women with reducing behavior risks and sustaining healthy lifestyle behaviors.