Content Staging / Web Farm / Database value changes not showing up

Are there any web farm sync tasks stuck in the web farm app? Do you receive any errors in either of the 3 servers in the event log?

Secondly, when you say you targeted a server for content staging, are you pushing the changes only to one server? You should be using a load balancer and a dns name. For instance server1 and server2 both use dns entry myserver.domain.com. So in your content staging setup you'd use myserver.domain.com vs. server1 or server2.

I can guarantee the issue is with caching but you also need to ensure you environment is configured correctly.

Is it absolutely necessary to resolve the content staging ASMX over the DNS name? The request gets routed to a single server anyways.

For security reason, we've actually disabled the ability to resolve the ASMX via DNS. The reason is due to Kentico's requirement for the ASMX to be publicly resolvable. We've setup server-side routing rules to deny request to the ASMX against the DNS. We only allow the staging content ASMX to be resolvable via the internal server name.

What troubles me is that even with a clear cache on one of the server, it doesn't seem to refresh the database originated content. What would cause that?

You're defeating the purpose of using a load balanced system if you're only targeting one server from your dev server. What happens when that one server goes down or isn't available when you're using content staging?

You can use certificates to perform your authentication for content staging so why not use that vs. a simple username/pass combo? Have you read the security whitepaper from Kentico?

If you're staging to server 1 and you clear the cache on server 1, it won't clear the cache on server 2. You need to do it on both or manually trigger it. I'd reach out to Kentico Support to specifics, especially if you're restricting access as specifically as you are.