How To Write A Letter To A Inmate In Prison . Then, take a regular envelope and pop your letter inside. You need to learn about what is acceptable to send, with things like money, food, and clothing usually forbidden. Love Letters From Prison August 2010 from lovelettersfromprison.blogspot.com We know that writing to an inmate can feel intimidating at first, so we’ve gathered up some sample letters of encouragement for inmates for you to use as templates as you start: A simple gesture, such as a supportive letter from a loved one, also goes a long way. Write your name and the return address on the envelope and in the letter.