Food, medications and Yom Kippur

Hi Rabbi, I have to take one single medication every day, preferably at the same time every day, and it must be taken with food (and water to help swallow). This is actually in the directions. What is the most halachically appropriate way I can keep to this and still fast?

ב"ה Shalom If the medicine required is not taken it can put the person, G-d forbid , in danger , and it cannot be taken without drink, one may take the medicine and drink water without altering the taste. My assumption is, that your case is one that if the medicine is not taken it can possibly cause illness, G-d forbid, but not danger. Therefore , since we have time until Yom Kippur you should consult an orthodox Jewish doctor and /or pharmacist who understand the severity of Yom Kippur, if you can possibly change you medicine regimen for one day and perhaps take it just before the start of Yom Kippur and then again immediately after the fast. Another alternative is to verify if the same medicine is available in suppository form and then it can be taken without question. Perhaps there is another brand or form of the same medicine in liquid or other which doesn't not require drinking before taking the pill. If you have already verified this, I apologize. In that case, I will simply follow what is written in Shemirat Shabbat Kehilchata (39:8) if the medicine is bitter you may swallow the medicine normally. If ,as you say ,it is required be taken with water, you must make the water bitter so that you don't enjoy the drink. Some suggest adding some strong unsweetened tea concentrate, baking soda or salt to be put in the water. (KI Ba Moed pg. 149) . All the best and stay well