This complex case study involves an offender who communicated online with numerous undercover (UC) officers from different agencies simultaneously. It began with the suspect communicating with a UC officer with the Grand Prairie Police Department, who was using two different UC child profiles. The case then became a joint investigation with the Garland Police Department, where a third UC child profile was used to communicate with the same offender. This effort resulted in an in-person meeting with the offender and what he believed to be two 12-year-old boys (cousins) for a sexual encounter. It was later learned that this offender previously communicated with two additional UC officers from Dallas and McLennon Counties. The offender was clearly ambitious, and fortunately he only communicated with UC law enforcement at every turn he made. The discussion will include the details of this operation, which included some very entertaining aspects, as well as some up and downs that were not all favorable for law enforcement. The lessons learned that resulted in procedural changes for future operations will also be shared.