I've spent the last six years building cloud infrastructure and CI/CD pipelines for healthcare and defense engineering teams. The same five mistakes keep showing up across every HIPAA engagement I take on, and none of them are about not knowing what HIPAA requires. Engineers in healthcare aren't dumb. They've read 45 CFR § 164. They know what audit logs are. They've sat through compliance training that lasted longer than their last on-call rotation. The problem is structural. Most CI/CD pipelines were designed for unregulated software, then bolted with compliance controls afterward. The result is pipelines that satisfy neither engineers nor auditors. Slow, brittle, and somehow still failing audits. Here are the five patterns I see most often, what goes wrong with each, and what actually works. 1. Treating compliance as a final gate The most common pattern: your pipeline runs build, test, and deploy as normal. Then somewhere near the end, a "compliance check" stage runs that produces a report.…