Infrared photodetectors are essential to many applications, including surveillance, communications, process monitoring, and biological imaging. The short-wave infrared (SWIR) spectral region (λ = 1–3 μm) is particularly powerful for health monitoring and medical diagnostics because biological tissues show low absorbance and minimal SWIR autofluorescence, enabling greater penetration depth and improved resolution in comparison with visible light. However, current SWIR photodetection technologies are largely based on epitaxially grown inorganic semiconductors, which are costly, require complex processing, and impose cooling requirements incompatible with wearable electronics. Solution-processable semiconductors are being developed for infrared detectors to enable low-cost direct deposition and facilitate monolithic integration and resolution not achievable using current technologies. In particular, organic semiconductors offer numerous advantages, including large-area and conformal coverage, temperature insensitivity, and biocompatibility, for enabling ubiquitous SWIR optoelectronics. This Account introduces recent efforts to advance the spectral response of organic photodetectors into the SWIR. High-performance visible to near-infrared (NIR) organic photodetectors have been demonstrated by leveraging the wealth of knowledge from organic solar cell research in the past decade. On the other hand, organic semiconductors that absorb in the SWIR are just emerging, and only a few organic materials have been reported that exhibit photocurrent past 1 μm. In this Account, we survey novel SWIR molecules and polymers and discuss the main bottlenecks associated with charge recombination and trapping, which are more challenging to address in narrow-band-gap photodetectors in comparison with devices operating in the visible to NIR. As we call attention to discrepancies in the literature regarding performance metrics, we share our perspective on potential pitfalls that may lead to overestimated values, with particular attention to the detectivity (signal-to-noise ratio) and temporal characteristics, in order to ensure a fair comparison of device performance. As progress is made toward overcoming challenges associated with losses due to recombination and increasing noise at progressively narrower band gaps, the performance of organic SWIR photodetectors is steadily rising, with detectivity exceeding 1011 Jones, comparable to that of commercial germanium photodiodes. Organic SWIR photodetectors can be incorporated into wearable physiological monitors and SWIR spectroscopic imagers that enable compositional analysis. A wide range of potential applications include food and water quality monitoring, medical and biological studies, industrial process inspection, and environmental surveillance. There are exciting opportunities for low-cost organic SWIR technologies to be as widely deployable and affordable as today’s ubiquitous cell phone cameras operating in the visible, which will serve as an empowering tool for users to discover information in the SWIR and inspire new use cases and applications