Internet Protocol Caption Telephone Services provide access to telecommunication for persons who are d/Deaf or Hard of Hearing as users can listen to and read captions of what the other speaker says. This paper presents the results of Applied Cognitive Task Analyses with d/Deaf or Hard of Hearing users to uncover the strategies experienced caption phone users deploy to address communication challenges. Results indicate that users learn strategies that involve adapting their communication behaviors, obtaining the collaboration of the other speaker, selecting the best technology for specific settings, and disclosing hearing loss. Some situations are particularly challenging, e.g., higher caption error when the other speaker has an “accent” or the conversation includes technical language; having to disclose hearing loss and thus risking negative consequences due to biases against disability. Findings can help accelerate novice users’ learning of strategies and inform the development of sociotechnical solutions for caption phones’ current shortcomings.