International Ocean Discovery Program (IODP) Expedition 385T aimed to take advantage of a transit of the R/V JOIDES Resolution from Antofagasta, Chile, to San Diego, California (USA), to accomplish new sampling and data collection from legacy borehole observatories in Deep Sea Drilling Project (DSDP) and Ocean Drilling Program (ODP) Holes 504B and 896A on the southern flank of the Costa Rica Rift. In addition, the US Science Support Program organized the participation of 3 Outreach Officers to evaluate the performance of the JOIDES Resolution Outreach Officer program as well as 2 educators and 12 undergraduate students for a shipboard “JR Academy.” Our scientific objectives were to collect (1) new Formation MicroScanner logs from Hole 504B for improving lithologic interpretations of crustal architecture at this archetype deep oceanic crust hole and (2) fluid samples from both holes for evaluating the crustal deep biosphere in deep and warm oceanic crust. These operations in Holes 504B and 896A have direct relevance to Challenges 5, 6, 9, 10, 13, and 14 of the IODP 2013–2023 Science Plan. Accomplishing both of these scientific objectives required the removal of old wireline CORK observatories, including associated inflatable packers that were installed in the cased boreholes in 2001. The fluid sampling plan also included testing a new Multi-Temperature Fluid Sampler. Despite successfully removing the CORK wellhead platforms from both holes, we were unable to remove the packers stuck in casing at both locations after 48 h of milling operations in Hole 504B and 2 h of milling operations in Hole 896A, thus precluding accomplishing any of the scientific objectives of the expedition. We provide an assessment of the final state of the holes and recommendations for possible future operations.