Hypertension is a common problem in people with diabetes and several changes have occurred to the joint Canadian Hypertension Education Program and Canadian Diabetes Association hypertension recommendations over the past 5 years. This article uses a case-based approach to review contemporary issues in hypertension management in the context of diabetes, including: treatment targets, optimal combination therapy, choice of diuretic therapy, the role of aldosterone antagonists, role of aliskiren, bedtime dosing of antihypertensive agents, benefits of sodium reduction, impact of lifestyle interventions, vascular risk reduction with antiplatelet therapy, adherence strategies, the role of home blood pressure monitoring, and treatment considerations based on ethnocultural background. Particular emphasis is given to linking the recommendations to practice. Up to 80% of people with diabetes and hypertension will die of cardiovascular disease, especially stroke. The 2012 Canadian Hypertension Education Program hypertension in diabetes key messages for knowledge translation are that clinicians should: 1) ensure people with diabetes are screened for hypertension, 2) assess blood pressure at all appropriate healthcare visits, 3) encourage home monitoring with approved devices, 4) initiate pharmacotherapy and lifestyle modification concurrently, 5) assess and manage all other vascular risk factors, and 6) enable sustained lifestyle and medication adherence.