There are many successful trials of CBT-I in those with MDD-I (Edinger et al., 2009b; Kuo et al., 2001; Lichstein et al., 2000; Manber et al., 2008; Morawetz, 2001; Watanabe et al., 2011). In each of these trials CBT-I was delivered unaltered. Nonetheless, CBT-I is a demanding treatment and MDD-I clients can present with specific barriers that can interfere with tolerating the rigors of the protocols, and make following the treatment more challenging. In this chapter, we provide some troubleshooting strategies for the more common problems. Cognitive therapy, as stated in Chapter 6, is an important tool for increasing adherence. We have included in this chapter some cognitive strategies that can be utilized for troubleshooting resistance, but the reader is directed to Chapter 6 to understand the theoretical underpinnings of such techniques.