Despite extensive training and ongoing experience, cases often appear which confer new diagnostic or therapeutic information or force the practitioner to consider diagnoses which are uncommon. A series of cases relating to cutaneous infectious disease are presented wherein a lesson was learned by the speaker. Examples include: the rare mani- festation of vegetative herpes in the immunocompromised, the development of Monkeypox acquired by an overseas traveller, the ability if infections to closely emulate inﬂ ammatory disorders (such as tinea imitating SCLE), the wide variety and non-speciﬁ city of deep fungal infection mor-phology, the ability of algae to cause skin lesions in the immunosuppressed patient, and the potential for hypersensitivity reactions against ectoparasites. Pearls to be learned in recent medical literature include: the use of liquid nitrogen cryoanesthesia for relief of post-herpetic neuralgia, the increased risk of stroke which accompanies herpes zoster ophthalmicus, and the potential to induce remission of orolabial herpes simplex outbreaks by use of occlusive imiquimod for three weeks during an attack. Finally: just a reminder that, although we possess improved treatments, HIV infection remains a serious global threat.