Is it not true though that even with the best will in the world - and the authority - the administration of patches in the corporate world in any organisation where the use of software goes beyond office and diary software is an achilles heel - anything that requires any specialist drivers or multi-site licenses will need (or it is perceived that it needs) testing thoroughly leading to delays in updating - plus the time it takes to package and update the corporate roll out
Sure, but this is only painful because IT is done badly as a whole. Fixing it for security reasons also fixes it as a whole.
Dev systems don't mirror test systems don't mirror preproduction systems don't mirror production systems (if they exist at all), so testing patches is fundamentally flawed.
Developers code badly and rely on the OS in ways they shouldn't, so patches that should have no affect on apps end up destroying APIs.
All these problems also make systems unreliable, slow, expensive to maintain and hard to recover - it's not just causing security problems.
The hard sell is this: You can either patch regularly and know when outages might happen, and prep for it, or you can sing "lalala I'm not listening" until wannacry wipes out your health service.