Late-winter lake ice regimes are controlled by water depth relative to maximum ice thickness (MIT). When MIT exceeds maximum water depth, lakes freeze to the bottom with bedfast ice (BI) and when MIT is less than maximum water depth lakes have floating ice (FI). Both airborne radar and space-borne synthetic aperture radar (SAR) imagery (Ku-, X-, C-, and L-band) have been used previously to determine whether lakes have a BI or FI regime in a given year, across a number of years, or across large regions. In this study, we use a combination of ERS-1/2, RADARSAT-2, Envisat, and Sentinel-1 SAR imagery for seven lake-rich regions in Arctic Alaska to analyze lake ice regime extents and dynamics over a 25-year period (1992–2016). Our interactive threshold classification method determines a unique statistic-based intensity threshold for each SAR scene, allowing for the comparison of classification results from C-band SAR data acquired with different polarizations and incidence angles. Additionally, our novel method accommodates declining signal strength in aging extended-mission satellite SAR instruments. Comparison of SAR ice regime classifications with extensive field measurements from six years yielded a 93% accuracy. Significant declines in BI regimes were only observed in the Fish Creek area with 3% of lakes exhibiting transitional ice regimes—lakes that switch from BI to FI during this 25-year period. This analysis suggests that the potential conversion from BI to FI regimes is primarily a function of lake depth distributions in addition to regional differences in climate variability. Remote sensing of lake ice regimes with C-band SAR is a useful tool to monitor the associated thermal impacts on permafrost, since lake ice regimes can be used as a proxy for of sub-lake permafrost thaw, considered by the Global Climate Observing System as an Essential Climate Variable (ECV). Continued winter warming and variable snow conditions in the Arctic are expected and our long-term analysis provides a valuable baseline for predicting where potential future lake ice regimes shifts will be most pronounced.