Introduction: The manifestations of syphilis are varied, and serology can establish the diagnosis early, especially in rare cases. We report a case of chancre redux (a rare recurrence of primary syphilis), which was embedded within a secondary syphilitic penile skin plaque. There were missed opportunities at earlier diagnosis as serology for syphilis was not ordered. Case presentation: A 56-year-old man presented with thickened penile plaques for five months. He reported a small penile ulcer approximately one month prior. There was no history of other skin lesions or rash. However, clinically there was an asymptomatic, indurated ulcer embedded within a plaque which was swab-positive for syphilis by PCR. A punch biopsy of a plaque was spirochaete-positive using an immunoperoxidase stain. The patient’s lesions resolved three weeks after treatment with intramuscular benzathine penicillin. Discussion: Uncommonly reported even in the preantibiotic era, chancre redux is now rare. The ulcer usually recurs at or near the site of the original chancre, and has similar morphological features. The skin lesions of secondary syphilis can exhibit remarkable morphological variety. The most common skin manifestation, a generalized macular rash, was not present at any time in this case. Rather, there were only a couple of nonspecific penile plaques. If biopsy is performed, histologic findings are variable, though typically the inflammatory infiltrate includes plasma cells. A special immunoperoxidase stain can highlight spirochaetes in biopsy sections. Conclusion: This case highlights the importance of considering syphilis in the differential diagnosis of persistent, atypical penile lesions and underscores the need for appropriate serological testing in such instances.