Periapical actinomycosis is a relatively rare form of cervicofacial actinomycosis, which typically involves the periapical region with subsequent potential spread to the jaw bones. We hereby present two cases of periapical actinomycosis. Both patients presented with jaw pain and “holes” in their gum and lacked the characteristic clinical features commonly seen in cervicofacial actinomycosis such as jaw mass, draining ulcers, sinuses and fistulae. The first patient was an immunocompetent host with chronic stable medical conditions but with a rather bad dentition requiring multiple recent teeth extractions. The second patient was edentulous, had refractory multiple myeloma, was on low-dose chronic steroids and pomalidomide therapy and therefore relatively immunocompromised. Both cases of actinomycosis were diagnosed by jaw bone histopathology, which showed characteristic sulfur granules and embedded Actinomyces-like organisms. The two patients had excellent clinical response to six months of penicillin therapy without any need for surgical intervention. The cases remind clinicians of including actinomycosis in the differential diagnosis of periapical lesions and illustrates the possibility of achieving cure with non-surgical treatment.