Letters You can communicate with your loved one in prison by writing letters to eachother. Each week a prisoner is allowed to send one free letter. If they want to send more than this then they need to purchase stamps and envelopes from the prison canteen. Alternatively, you can post self-addressed stamped envelopes to the prisoner so they can post letters back to you. If a prisoner is on remand then they are allowed to send 2 free letters a week.