Comment by freedomben

The biggest problem there is that it's a statistical gamble, and often times the damage isn't apparent for months or years later, which is plenty far enough removed from the decision that the manager isn't going to remember let alone realize "he told me so." And you reporting "I told you so" even in very easy, factual, and respectful professional language will typicall not be well received. There's also a decent chance that when the thing breaks or you get breached, you'll be blamed for it, or at least be on the defensive.

Now that said, I've worked with a lot of IT/engineering people who are pretty obstructionist to normal business operations and sometimes need to be told, "yeah, we're accepting the risk, move forward with the plan." Sometimes it's for good reasons, other times it's just our normal humanity asserting itself in different ways. It's a hard problem for sure.