Despite many studies on Adélie penguin breeding phenology, understanding the drivers of clutch initiation dates (CIDs, egg 1 lay date) is limited or lacks consensus. Here, we investigated Adélie penguin CIDs over 25 years (1991-2016) on two neighboring islands, Torgersen and Humble (<1 km apart), in a rapidly warming region near Palmer Station, Antarctica. We found that sea ice was the primary large-scale driver of CIDs and precipitation was a secondary small-scale driver that fine-tunes CID to island-specific nesting habitat geomorphology. In general, CIDs were earlier (later) when the spring sea ice retreat was earlier (later) and when the preceding annual ice season was shorter (longer). Island-specific effects related to precipitation and island geomorphology caused greater snow accumulation and delayed CIDs by ~2 days on Torgersen compared to Humble Island. When CIDs on the islands were similar, conditions were mild with less snow across breeding sites. At Torgersen Island, the negative relationship between CID and breeding success highlights detrimental effects of delayed breeding and/or snow on penguin fitness. Past phenological studies reported a relationship between air temperature and CID, assumed to be related to precipitation, but we found air temperature was more highly correlated to sea ice, revealing a misinterpretation of temperature effects. Finally, contrasting trends in CIDs based on temporal shifts in regional sea ice patterns revealed trends toward earlier CIDs (4-6 day advance) from 1979 to 2009 as the annual ice season shortened, and later CIDs (7-10 day delay) from 2010 to 2016 as the annual ice season lengthened. Adélie penguins tracked environmental conditions with flexible breeding phenology, but their life history remains vulnerable to subpolar weather conditions that can delay CIDs and decrease breeding success, especially on landscapes where geomorphology facilitates snow accumulation.