For decades, firms and individuals have utilized written documents to aid in the negotiation of, and completion of, business transactions. One such document is known as a "letter of intent." A letter of intent is often in the form of a letter that serves to evidence preliminary discussions and aid in negotiations between parties. They are generally intended to be "non-binding," meaning neither party will be bound by terms or conditions set forth in the letter of intent unless formal documents are later prepared and executed by the parties. Letters of intent take myriad forms and names, such as "memorandum of understanding," "proposal letter," and "letter of interest." They have been used in many areas of business, including finance, real estate, and supply chain management. Parties often choose to use a letter of intent for varied benefits it may provide, memorializing preliminary discussions, establishing a timeline for negotiations, seeing whether there are any "deal breakers" among terms being proposed, confirming that a party is serious about a deal, or putting moral pressure on the other party to continue negotiations. However, letters of intent carry with them a significant level of risk, which raises the question of whether or not they should be used at all. Many of the risks associated with the use of a letter of intent stems from the potential for a court to find that a letter of intent constitutes a binding agreement, or creates a duty of the parties to continue negotiations in good faith. Parties to a letter of intent may later disagree as to whether they intended all of the terms, or a particular provision, to be legally binding and enforceable, resulting in legal action. Even if a court finds that a letter of intent does not constitute a binding contract, a party may be able to recover damages under a number of legal theories, such as breach of a duty to negotiate in good faith or promissory estoppel. The use of letters of intent is therefore risky, and ultimately, the risks may outweigh the benefits of utilizing letters of intent. This thesis studies the types, uses, benefits, and risks associated with the use of letters of intent, including an examination of statutes and cases that have been applied by courts in disputes surrounding their use. Ways to mitigate the risks of use are also examined including simple practices such as not signing a letter of intent and using a separate document for any terms which must be binding, such as a "no shop" clause. A proposed legislative solution is also discussed that would prevent letters of intent not explicitly intended to be binding and meeting statutory requirements from being enforced in court, thereby substantially reducing the risks associated with the use of letters of intent.