A growing suite of SWIR imaging agents have recently been developed, with notable examples coming from the cyanines, xanthenes, and BODIPY families. However, these examples are hydrophobic and intrinsically prone to aggregation. While nanoparticle formulations can potentially offset these drawbacks, it is preferable to develop complementary SWIR dyes that do not require encapsulation for in vivo imaging. In this study, we strategically remodeled the hemicyanine dye (HD) (a common NIR platform) for multimodal SWIR FL and PA imaging. Of note, complementary remodeling efforts have yielded PA and NIR-II analogs. However, in the present study, we selected this platform owing to its relatively small size and ease of conversion into activity-based sensing probes. Unfortunately, these favourable properties come at a cost because HDs are essentially truncated cyanines which are blue shifted by ~100 nm. To compensate for the loss of π-conjugation, we introduced two key structural modifications using a modular synthetic route. Importantly, the best dye (SWIR-HD) we prepared,