Patients with penile conditions comprise a significant proportion of any pediatric urology practice, and physical examination is the mainstay of diagnosis for such conditions. While the rapid adoption of telemedicine (TM) facilitated access to pediatric urology care during the pandemic, the accuracy of TM-based diagnosis for pediatric penile anatomy and pathology has not been studied. Our aim was to characterize the diagnostic accuracy of TM-based evaluation of pediatric penile conditions by comparing diagnosis during the initial virtual visit (VV) with a subsequent in-person visit (IPV). We also sought to assess the agreement between scheduled and actual surgical procedure performed. A single-institution prospective database of male patients less than 21 years of age who presented for evaluation of penile conditions between August 2020 and December 2021 was analyzed. Patients were included if they had an IPV with the same pediatric urologist within 12 months of the initial VV. Diagnostic concordance was based on a surgeon-reported survey of specific penile diagnoses, completed at both initial VV and follow-up IPV. Surgical concordance was assessed based on the proposed versus billed CPT code(s). Median age among 158 patients was 10.6 months. The most frequent VV diagnoses were penile adhesions (n=37), phimosis (n=26), "other" (n=24), post-circumcision redundancy (n=18), and buried penis (n=14). Initial VV and subsequent IPV diagnoses were concordant in 40.5% (64/158); 40/158 (25%) had partial concordance (at least one diagnosis matched). There was no difference in age, race, ethnicity, median time between visits, or device type between patients with concordant vs. discordant diagnoses. Of 102 patients who underwent surgery, 44 had VV only while 58 had IPV prior to surgery. Concordance of scheduled versus actual penile surgery was 90.9% in those patients who only had a VV prior to surgery. Overall, surgery concordance was lower among those with hypospadias repairs vs. non-hypospadias surgery (79.4% vs. 92.6%, p=0.05). Among pediatric patients being evaluated by TM for penile conditions, there was poor agreement between VV-based and IPV-based diagnoses. However, besides hypospadias repairs, agreement between planned and actual surgical procedures performed was high, suggesting that TM-based assessment is generally adequate for surgical planning in this population. These findings leave open the possibility that, among patients not scheduled for surgery or IPV, certain conditions might be misdiagnosed or missed entirely.