Objective: To review current pragmatic issues and controversies related to tympanostomy tubes in children, in the context of current best research evidence plus expert opinion to provide nuance, address uncertainties, and fill evidence gaps. Methods: Each issue or controversy is followed by the relevant current best evidence, expert insight and opinion, and recommendations for action. The role of expert opinion and experience in forming conclusions is inversely related to the quality, consistency, and adequacy of published evidence. Conclusions are combined with opportunities for shared decision-making with caregivers to recommend pragmatic actions for clinicians in everyday settings. Results: The issues and controversies discussed include (1) appropriate tube indications, (2) rationale for not recommending tubes for recurrent acute otitis media without persistent middle ear effusion, (3) role of tubes in at-risk children with otitis media with effusion, (4) role of new, automated tube insertion devices, (5) appropriateness and feasibility of in-office tube insertion in awake children, (6) managing methicillin-resistant Staphylococcus aureus acute tube otorrhea, and (7) managing recurrent or persistent tube otorrhea. Conclusions: Despite a substantial, and constantly growing, volume of high-level evidence on managing children with tympanostomy tubes, there will always be gaps, uncertainties, and controversies that benefit from clinician experience and expert opinion. In that regard, the issues discussed in this review article will hopefully aid clinicians in everyday, pragmatic management decisions.