Cutaneous diphtheria, caused by toxin-producing Corynebacterium diphtheriae, has re-emerged as a clinically relevant infection in wound management. Global travel, tropical deployments, and migration have contributed to its reappearance in Europe and highlight its importance for both civilian healthcare and military medical services. We report two toxin-positive cases demonstrating the diverse epidemiological backgrounds of cutaneous diphtheria. The first case involved a 14-year-old migrant from Afghanistan who presented with multiple ulcerations of the extremities in the context of superinfected scabies. Microbiological testing revealed a toxin-producing C. diphtheriae strain along with Streptococcus pyogenes and methicillin-resistant Staphylococcus aureus (MRSA). The second case involves a 63-year-old male patient who developed ulcerative lesions on both lower legs and the left gluteal region after a six-week stay in the Philippines. Cultures confirmed toxin-positive C. diphtheriae with co-infection by S. aureus and S. pyogenes. The patient showed rapid improvement after antibiotic switch to clindamycin and topical antiseptic wound therapy. These cases underscore the ongoing risk of C. diphtheriae infection through migration and international travel. In the context of military medicine, such infections are of particular relevance for wound care in deployment and field settings, where tropical exposure, contaminated injuries, and limited laboratory access can complicate diagnosis and containment. Preventive measures, including up-to-date vaccination, early microbiological testing with toxin detection, and strict wound hygiene remain essential to mitigate operational and public health risks.