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APM and VIP Targeting Configuration Issues
From my testing I was able to get the Virtual to Virtual targeting to work.
I believe the issue you are running into two issues. 1. You are switching APM Policies based on the HTTP::host variable and that information will not be available when negotiating DTLS 1. You have the HTTP profile applied to the external virtual since you are using the HTTP::host method
Make sure the externally exposed virtual has both the ClientSSL and ServerSSL Profile applied and try removing the HTTP profile from the virtual.
Instead of using the HTTP::host method to identify the destination FQDN you will have to use the SNI attribute of the client ssl request. Take a look at TLS Server Name Indication for some great information on SNI
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