Background Leveraging internet-based communication tools (eg, messaging apps, SMS text messaging, and email) may be an effective avenue for delivery of HIV prevention messages to men who have sex with men (MSM) in India, but there are limited models for such internet-based interventions. Objective The CHALO! pilot was an online educational and behavioral intervention aimed to determine the feasibility, acceptability, and preliminary impact of a peer-delivered, internet-based messaging intervention for HIV testing and consistent condom use for MSM in India. The messages addressed barriers to HIV testing and condom use and were theoretically based on the information-motivation-behavioral skills model. Methods Between February and March 2015, we recruited, enrolled, and randomized 244 participants via online advertisements on mobile dating apps and Facebook. Eligible men (18 years or older, sexually active with other men, and self-reported HIV-negative or unknown status) were randomized to receive educational and motivational messages framed as either approach (ie, a desirable outcome to be achieved) or avoidance (an undesirable outcome to be avoided) over 12 weeks via internet-based messaging platforms. Participants completed online surveys at baseline and immediately postintervention. Results Participants were similar across arms with respect to sociodemographic and behavioral characteristics. Over 82.0% (200/244) of participants were retained (ie, viewed final messages), and 52.3% (130/244) of them completed the follow-up survey. Of those completing the follow-up survey, 82.3% (107/130) liked or strongly liked participating in CHALO!. The results showed a significant increase in self-reported HIV testing in the past 6 months from baseline to follow-up (41/130, 31.5% to 57/130, 43.8%; P =.04). When including those who reported intentions to test, this percentage increased from 44.6% (58/130) at baseline to 65.4% (85/130) at follow-up ( P <.01). When examining intentions to test among those without prior HIV testing, intentions increased from 32% (16/50) of the sample at baseline to 56% (28/50) of the sample at follow-up ( P =.02). Condom use during anal sex did not significantly change from baseline to follow-up. HIV testing and condom use did not significantly differ between approach and avoidance conditions at follow-up. Conclusions As one of the first studies of an online HIV prevention intervention for Indian MSM, CHALO! was feasible to implement by a community-based organization, was acceptable to participants, and demonstrated potential to improve HIV testing rates.