In October, 2016, the Internal Revenue Service issued temporary and proposed regulations under Internal Revenue Code Sections 752 and 704 (“the 2016 Regulations”). The author reviews and analyzes these regulations, and concludes that the 2016 Regulations properly deny economic risk of loss for unduly remote bottom dollar guarantees. He also concludes, however, that the IRS exceeded its regulatory authority when it also denied economic risk of loss on bottom-dollar guarantees where the risk to the guarantor was not remote. In addition, he observes that the 2016 Regulations lead to an inappropriate disjuncture with Section 465 and create rules that are too vague for real-world application. He argues that, at a minimum, the 2016 Regulations should be brought into compliance with the IRS’s authority and be subject to a de minimis rule. But his primary recommendation is that the 2016 Regulations be withdrawn and replaced with anti-abuse rules.