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HTTPS Monitor Questions

Maybe I am just thinking this through wrong so hopefully the people out in THWACK land can assist.  We have a web server running a few different websites and the sites are using the same IP address.  I was going to setup each as an extra site then configure an HTTPS monitor for each to test to see if the site goes down via a string of words.  I am having an issue with this because both sites use the same IP so I can't add them separately.  So this may not be a viable solution.  But I do have AppInsights for IIS installed and monitoring IIS - I know I can setup an alert via IIS that when the site goes down to send out an alert which I can do but I also would like to try to be able to monitor if the site goes down and for some strange reason IIS says it is still up. 

I hope above makes sense.  

Thanks

Dave