Operant chambers are small enclosures used to test animal behavior and cognition. While traditionally reliant on simple technologies for presenting stimuli (e.g., lights and sounds) and recording responses made to basic manipulanda (e.g., levers and buttons), an increasing number of researchers are beginning to use Touchscreen-equipped Operant Chambers (TOCs). These TOCs have obvious advantages, namely by allowing researchers to present a near infinite number of visual stimuli as well as increased flexibility in the types of responses that can be made and recorded. We trained wild-caught adult and juvenile great-tailed grackles (Quiscalus mexicanus) to complete experiments using a TOC. We learned much from these efforts, and outline the advantages and disadvantages of our protocols. Our training data are summarized to quantify the variables that might influence participation and success, and we discuss important modifications to facilitate animal engagement and participation in various tasks. Finally, we provide a “training guide” for creating experiments using PsychoPy, a free and open-source software that was incredibly useful during these endeavors. This article, therefore, should serve as a resource to those interested in switching to or maintaining a TOC, or who similarly wish to use a TOC to test the cognitive abilities of non-model species or wild-caught individuals.