The implementation of virtual reality (VR) has gained popularity in the organizational settings in responding to the digital transformation in the era of Industry 4.0. VR offers immersive and authentic experiences for learners through simulated real-life scenarios during training. While the affordances have been widely discussed, there is a need to take a systems thinking approach and look at the challenges and side effects associated with the implementation. This systematic review is an effort to comprehensively understand the challenges and side effects along with the exploration of contexts, affordances, and attitudes toward VR applications of the VR initiative for training in organizational contexts. Following a ground theory approach, we analyzed 50 articles published since 2011 that covered a wide range of industries and locations worldwide. The findings from our analysis revealed multiple affordances, challenges, and side effects of applying VR in training. We hope to promote a discussion on VR integration, especially to caution researchers and practitioners the challenges and side effects of this initiative in the design and implementation process, to derive maximum value of the immersive technologies in learning. The results contribute to a comprehensive understanding of applying VR in organizational settings and informs design considerations for successful VR implementation in training programs.