Children, teenagers and young adults should get their blood pressure checked at least once every 5 years. Given the new guidelines, I recommend that this same group get their blood pressure checked at least once annually. As you age, your blood pressure is likely to increase and should be checked more often. If you have any type of underlying chronic illness, more frequent blood pressure checks are mandatory. Your blood pressure fluctuates during the day, so when you start tracking your blood pressure, you should check it at different times of the day, about 5-6 times. If you have already been diagnosed with hypertension and are taking high blood pressure medication, your blood pressure measurements should coincide with your doses. The best time to check it is before you take your medication. Your primary care physician should provide you with education and recommendations for a routine to check your own blood pressure and track those results in a blood pressure diary.