The Penn State X-ray detector lab, in collaboration with Teledyne Imaging Sensors (TIS), have progressed their efforts to improve soft X-ray Hybrid CMOS detector (HCD) technology on multiple fronts. Having newly acquired a Teledyne cryogenic SIDECARTM ASIC for use with HxRG devices, measurements were performed with an H2RG HCD and the cooled SIDECARTM. We report new energy resolution and read noise measurements, which show a significant improvement over room temperature SIDECARTM operation. Further, in order to meet the demands of future high-throughput and high spatial resolution X-ray observatories, detectors with fast readout and small pixel sizes are being developed. We report on characteristics of new X-ray HCDs with 12.5 micron pitch that include in-pixel CDS circuitry and crosstalk-eliminating CTIA amplifiers. In addition, PSU and TIS are developing a new large-scale array Speedster-EXD device. The original 64 × 64 pixel Speedster-EXD prototype used comparators in each pixel to enable event driven readout with order of magnitude higher effective readout rates, which will now be implemented in a 550 × 550 pixel device. Finally, the detector lab is involved in a sounding rocket mission that is slated to fly in 2018 with an off-plane reflection grating array and an H2RG X-ray HCD. We report on the planned detector configuration for this mission, which will increase the NASA technology readiness level of X-ray HCDs to TRL 9.