This paper discusses the Federal Child Support Guidelines [Guidelines], with an emphasis on understanding common misapplications of the Guidelines. In particular, the author focuses on sections 4 (high incomes), 7 (special or extraordinary expenses), 9 (shared parenting), and 10 (undue hardship) of the Guidelines, providing a detailed discussion of these sections and a comprehensive review of Alberta’s judicial interpretation and application of these sections in the relevant case law. In addition, practical suggestions and tips regarding best practices are included, with a view to developing creative solutions as an alternative to litigation and/or options for the court if litigation proceeds. Finally, the issue of using life insurance coverage as security for child support obligations is also briefly examined.