We review successes and challenges from five recent subglacial bedrock drilling campaigns intended to find evidence for Antarctic Ice Sheet retreat during warm periods in the geologic past. Insights into times when the polar ice sheets were smaller than present serve as guiding information for modeling efforts that aim to predict the rate and magnitude of future sea level rise that would accompany major retreat of the Antarctic Ice Sheet. One method to provide direct evidence for the timing of deglaciations and minimum extent of prior ice sheets is to extract subglacial bedrock cores for cosmogenic nuclide analysis from beneath the modern ice sheet surface. Here we summarize the lessons learned from five field seasons tasked with obtaining bedrock cores from shallow depths (>120 m beneath ice surface) across West Antarctica since 2016. We focus our findings on drilling efforts and technology and geophysical surveys with ground-penetrating radar. Shallow subglacial drilling provides a high risk, high reward means to test for past instabilities of the Antarctic Ice Sheet, and we highlight key challenges and solutions to increase the likelihood of success for future subglacial drilling efforts in polar regions.