Hi, Patrick.
Thanks for the detailed steps.
> You need to "delete" the certificate entry using keytool and then insert the new one. Without that step some stuff breaks.
Yes, you are right, it's mandatory steps. At least, you must import the new one to the default java certificate storage, but it's also recommended to remove the old one too, it was reported leaving it there may cause issues.
Thanks again for sharing results of your research, we'll update docs accordingly.