It wasn't misinterpreted, I even wrote dated examples out.
The permission to stay for 1 year from an O-A visa and permission to stay from an extension based on retirement are different, in that they are given for different reasons.
One is subject to the conditions set by the type of valid Visa, the other is subject to the conditions set by the local Immigration rules.
The examples were thus.
O-A issued and entry Jan 2018, with a second entry Jan 2019 with permission to stay until Jan 2020.
In that scenario the very first extension of permission to stay based on retirement will be effective after 31st October, therefore Insurance will be requested.
O-A issued and entry Jan 2017, with a second entry Jan 2018 with permission to stay granted until Jan 2019.
In Jan 2019 you extended your permission to stay based on the requirements and criteria set out in Police orders.
In Jan 2020 no Insurance is requested because you previously extended on the basis of retirement before the amendment became effective on 31st Oct 2019.
Those were the examples and the answers I previously posted to the above question.
We will have to wait until after October 31st to see whom and under what criteria is affected for a definitive answer, but I'd guess as usual we'll have different offices with different interpretations.
I can still interpret it with two different meanings, even after the explanation I received.