Solid oral dosage forms such as tablets and capsules are generally the preferred method of drug delivery due to their convenience, cost, and acceptability. However, for many people, it can be a challenge to swallow solid oral medications, even those with healthy swallowing function. This review describes current strategies available to facilitate medication administration to otherwise healthy people with pill-swallowing difficulties. In general, restoring and maintaining the ability to swallow pills whole should ideally be the first choice in managing people with pill-swallowing difficulties. A number of strategies can potentially make it easier to swallow pills whole. These include postural adjustments, using pill-swallowing aids, and teaching pill-swallowing techniques. Where these are not successful or appropriate, then other approaches have to be considered using alternative formulations/routes of administration or deprescribing. If there is no other option, and it is not directly contraindicated for each specific medication dosage form, pills may be modified and mixed in foods and drinks to aid swallowing. In conclusion, people with pill-swallowing difficulties can benefit from a number of strategies designed to facilitate swallowing medications. However, these strategies should be further evaluated with regard to the evidence relating to both their efficacy and safety.