Some customers today require airgapped solutions for various reasons from basic security to protecting proprietary intellectual property and services. While airgapping inherently makes systems more difficult to access, this advantage seriously inconveniences any practices to streamline a DevSecOps flow. Some key areas of concern are automating tests, staging data, and managing remote teams in multiple environments. Basic DevSecOps cultural change focuses on the 3 Ways and CALMS but customer requirements impeding flow require their own learning. Pipelines through not just multiple environments but several air-gapped environments can create needless repetition and data movement challenges unless carefully integrated. Our team struggled to get back to basic principles but did find some solutions. These solutions found areas to conveniently stop the pipeline, structuring teams for efficiency, and coordinating multiple communication channels. While airgapped development posed the first challenge, our second involved additional gaps between test and production environments, and a lack of system mirroring. The challenges we faced, and our solutions to date can help inform others on their own paths in complicated security environments.