Extensor pollicis longus rupture is rare but debilitating condition that has several etiologies. The injury and its aftermath causes serious disability affecting activities of daily living and vocational ones. Repetitive stress due to occupational work has been reported rarely as an associated condition with this injury. The history of neglect of the rupture often compounds the problem with a resultant gap between tendon ends not amenable to direct repair. A free tendon graft of ipsilateral palmaris longus tendon was used by us in our case with excellent regain of function. Presented case highlights a rarely reported occurrence of injury in a tailor following repetitive strain and managed herewith leading to a good functional outcome.