This is the second article in a two-part series explaining the mechanics of 10b5-1 plans and their application to the private funds industry; examining the lessons that can be learned from an inquiry into possible insider trading by a major private equity fund manager that purchased debt of a portfolio company pursuant to a 10b5-1 plan (the inquiry ultimately determined that the trading had not violated insider trading restrictions); and recommending practices that may enhance the defensibility of a 10b5-1 plan. The authors of the series are Daniel Laguardia, a partner in Shearman & Sterling’s Litigation Group, and K. Mallory Brennan and Ross Kamhi, both associates in that group. See also “The Best-Laid Plans: Preventing Rule 10b5-1 Plans from Going Awry (Part One of Two),” Hedge Fund Law Report, Vol. 7, No. 22 (Jun. 6, 2014).