The message about the length of the ClientHello isn't causing this problem (and should probably be removed, because almost every middlebox that had a problem with long ClientHello messages was fixed over 5 years ago).
The problem you're encountering is almost certainly caused by the fact that Apple is using Certificate Pinning for the icloud.com server. See http://fiddler.wikidot.com/certpinning
ADMIN
Nick Iliev
Posted on:29 May 2020 08:59
Hello,
Can you confirm that you have followed the steps required to enable capturing traffic from an iOS device? See the related documentation here. Alternatively, check if you are facing this issue related to different versions of TLS. In the very same thread, you will also find that some applications are using an extra layer of security through certificate pinning (see details here).
If your issue still persist, you could send us the exact steps you are taking so that we could reproduce the issue.
Regards,
Nick Iliev
Progress Telerik
Progress is here for your business, like always. Read more about the measures we are taking to ensure business continuity and help fight the COVID-19 pandemic. Our thoughts here at Progress are with those affected by the outbreak.