Imatinib, an inhibitor of tyrosine kinases is a low molecular weight, anticancer agent approved for various hematological and non hematological malignancies. It also inhibits stem-cell factor receptors c-KIT, Bcr-Abl, and platelet derived growth factor. Its use in dermatology is accounted for metastatic dermatofibrosarcoma protuberans, sclerodermous graft-versus-host disease, systemic sclerosis and others. Imatinib is generally well tolerated. Some associated side effects are gastrointestinal upset, weight gain, muscle cramps and cutaneous effects. Cutaneous adverse effect is the most common including non specific maculopapular exanthem, superficial edema, acute generalized exanthemataous pustulosis, lichenoid reaction, Stevens-Johnson syndrome, pityriasis rosea like eruption, photosensitization, pigmentary changes, and others. We report a case of a pityriasis rubra pilaris like eruption after two initiation of Imatinib. There are paucity of literature of imatinib induced pityriasis rubra pilaris like eruptions.