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Our flags are dynamic. Service basically reads them from an env var at runtime to determine if requests go through.
Security, at my place at least, has been very conservative about not launching stuff into prod until they've pentested in our test stage which has kinda forced us to do waterfall :|
Sounds rough. My fiancé does security, and from what I've gathered from him, the best time for security to get involved is at the design stage. They look over the proposal, give their input, and then nobody's surprised at release time, and teams can follow agile practices. Obviously there's still a review of the final product, but that can be done asynchronously after the fact to confirm that best-practices were followed.
Easy to say, hard to put into practice. Certainly depends on the kind of service your business provides.