Large-scale sell-offs of industrial timberlands in the United States have prompted public and private investments in a new class of “working forest” land deals, notable for their large size and complex divisions of property rights. These transactions have been pitched as “win-win-win” deals that provide social, economic, and ecological benefits. Despite hundreds of millions of dollars invested in these transactions, we found a paucity of evidence that their supposed benefits are being realized. Monitoring programs necessary to gather such evidence tend to be underfunded, short term, and focused on a limited set of indicators. The few projects with more comprehensive monitoring programs had long-term funding sources, formal mechanisms for incorporating data into subsequent management decisions, and combined multidisciplinary monitoring techniques. We propose that a relatively modest allocation of funds to monitoring could help assess—and hopefully improve—the effectiveness of current and future transactions, to see if the promise of “win-win-win” is actually delivered.