We report an unusual case of acute septic olecranon bursitis, with probable olecranon osteomyelitis, where the only organism isolated in culture was initially considered a contaminant, Cutibacterium acnes. However, we ultimately considered it the likely causal organism when treatment for most of the other more likely organisms failed. This typically indolent organism is prevalent in pilosebaceous glands, which are scarce in the posterior elbow region. This case illustrates the often challenging empirical management of a musculoskeletal infection when the only organism isolated might be a contaminant, but successful eradication requires continued treatment as if it is the causal organism. The patient is a Caucasian 53-yearold male who presented to our clinic with a second episode of septic bursitis at the same location. Four years prior, he had septic olecranon bursitis from methicillin-sensitive Staphylococcus aureus that was treated uneventfully with one surgical debridement and a one-week course of antibiotics. In the current episode reported here, he sustained a minor abrasion. Cultures were obtained five separate times because of no growth and difficulty eradicating the infection. One culture grew C. acnes on day 21 of incubation; this long duration has been reported. The first several weeks of antibiotic treatment failed to eradicate the infection, which we ultimately attributed to inadequate treatment of C. acnes osteomyelitis. Although C. acnes has a well-known propensity for false-positive cultures as typically reported in post-operative shoulder infections, treatment for our patient's olecranon bursitis/osteomyelitis was successful only after several surgical debridements and a prolonged course of intravenous and oral antibiotics that targeted it as the presumptive causal organism. However, it was possible that C. acnes was a contaminant/superinfection, and another organism was the culprit, such as a Streptococcus or Mycobacterium species that was eradicated by the treatment regime targeted for C. acnes.