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After you apply the EIP to the instance, it's a good idea to restart the instance. The EIP will take affect with the ArcGIS Server configuration and it should work for you. If it does not, then the next thing to look at is the Security Groups to ensure that external access to the server is open. Security Groups in EC2 is basically the firewall for machines within that group. If this hasn't been configured properly, you could be blocking external http requests from hitting the instance.
Hope that helps,
Turns out the Security Group settings is exactly what the issue was. Originally the only ports open were for Remote Desktop and HTTPS access. As soon as I enabled HTTP, everything started working as it should. Thanks for pointing me in the right direction!
In the near future, we will require HTTPS access, as Amazon is going to be used as a failover for our secured external on-site AGS instance. Is there anything that I need to take into consideration in order to get Amazon to work seamlessly with HTTPS and our set up?
As long as you install the SSL Cert on the Amazon instance, and test it out you should be good to go. I would still give this link a quick read to make sure you've covered all your bases.