Introduction: In India, Sexually transmitted infections (STI) have variability in prevalence across differentsubregions and subpopulations practicing high-risk behavior (the gender incongruent individuals, commercialsex workers, truck drivers etc.). Prevalence of syphilis in gender incongruent individuals is a gray area due tostigma and discrimination associated with the diagnosis. Contact tracing is a boon in better handling the publichealth burden of STIs. The current case series is to highlight the resurgence of syphilis in gender incongruentindividuals and to underscore the importance of screening and contact tracing for the same for public good.Methods: Twenty one gender incongruent individuals testing positive for Syphilis with the Rapid Reagin Test(RPR) in a period of a year at the Malvani Urban Health Training Center (UHTC), Malvani Slum, Malad, Mumbai;were included in the study.Results: The RPR titres ranged from 1:2 to 1:64. Out of these twenty one, 4 of them were found to be HIV coinfected.They were counseled and treated according to the standard guidelines. Contacts of partners whom theyhad intercourse with, in past 3 months could not be traced, as a result of which partner management couldn’t bedone.Conclusions: Better patient awareness through counseling and incorporation of information technology can aid intackling the problem of non compliance with contact tracing. Active screening for HIV should be done in patientswith STI.