The most important thing in the mail you received from UKVI is
Please note the onus is upon individual customers to ensure that they satisfy the requirements set out in the guidance material.
As i set out in my last response, I agree with Zimba in that you can apply for ILR 28 days before 15/10. No disputes on that.
The link Zimba provided clearly says that is the only required condition for a successful application. The email you received says otherwise.
I personally agree with the newer letter.
Applying for ILR when the existing visa does not cover the full 5 year period carries a very small risk. If the CW processes your application before the 15th, they would have to reject the application as you only complete 5 years of lawful stay on the 15th, as per my reading of the immigration rules.
It is highly unlikely the application will be processed that fast so I would not worry about it, but as the UKVI letter said - you need to know about it and it is your responsibility.
If I were in your place, I would do what I said in my last post. Apply for ILR closer to the visa expiry date and delay the biometrics to make as sure as possible that my application will not be processed before the 15th. It does not eliminate the risk but makes it almost zero.
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