Most settlements work. The ones that fail do so in a small number of recognizable ways, and this article walks through each of them. It starts with formation, and why an exchange of emails can bind a client who thought nothing was final until the long-form document was signed. It then covers the release itself, the difference between claims that arose and claims that are known, and the waiver language that decides whether a settlement buys peace or only buys the lawsuit already filed. Later sections cover the claims that cannot be released in the ordinary way at all, including age discrimination waivers under the OWBPA, wage claims requiring approval, and the right to file an administrative charge, and the increasingly constrained law of confidentiality and non-disparagement after McLaren Macomb, the Speak Out Act, and the tax provision that penalizes confidential harassment settlements. The article closes with the money problems that surface after signing: the taxation and reporting of settlement proceeds, the statutory and contractual lienholders who appear once a plaintiff is paid, and the two sentences in a dismissal order that determine whether a court can enforce the deal at all.