I fortunately have not gotten a single SSSS since I started frequent flight (nearly 100 flights last year, 60 the previous year, several this year so far). I've held clearance for most of that time, but have never figured that had anything to do with it; the DoD (or other agency for those with, say, DoE clearances, etc.) is not going to share their DBs with the TSA. Not going to happen!!!

What I DO find funny about flying and holding clearance is that places like MCO that have the silly "pay us extortion and we won't play shoe carnival with you" program still run a background check on you when you sign up... a background check that is many orders of magnitude less thorough than the one you've already undergone.