Upgrade to Tomcat 8.5 gives 500 internal server for working application URL - iis-8.5

I upgraded Tomcat server from 8.0 to 8.5. The web server is IIS. Binding in IIS server was www.test.abcurl.com for port 80. The application URL is http://test.abcurl.com.
After the upgrade, http://test.abcurl.com returns 500 internal server error.
But,
1) http://test.abcurl.com:8080 works
2) I changed the binding from www.test.abcurl.com to test.abcurl.com in IIS and http://test.abcurl.com started working.
Both 1) and 2) puzzle me. How is this related to Tomcat upgrade to 8.5? Please help to enlighten.
P.S: I had also tried changing connector port to 80 in server.xml initially, which did not work.

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App runs on local Tomcat instance, but gives 404 on virtual server with identical software and setup

I have a Vaadin and Spring Boot app that runs in the Tomcat instance on a local server.
Whenever I deploy it to the Tomcat instance on a virtual server hosted by a provider, I get a 404 and the application log isn't created. There are no errors in any Tomcat logs and Tomcat manager shows the app as running.
I've deployed another Vaadin / Spring Boot app to that same Tomcat instance that's just a static html page and it both runs and creates an application log. I've ran the app on an old mac with the same amount of memory as the virtual server just to rule out a memory issue.
Both my local server and the virtual server are running Debian with the same versions of Java and Tomcat. The only software difference I'm aware of is my local server is Debian 10 and the virtual server is Debian 9. No other software has been installed except UFW which is disabled.
The virtual server has no other firewalls. I tried adding a static html page to the project root, and that gives a 404 too.
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How to configure Tomcat as response to DNS request?

Hope you're all doing fin!
I'm working at a company where the main application is at a web page made with Java. It deploys with Tomcat on a server with Microsoft Windows Server 2008 R2 O.S. I've recently made some changes on this application, but the development environment is not on Tomcat but on JBoss and the former developers knew how to deploy the development from JBoss to Tomcat, but didn't leave any documentation on how to do that.
My problem is that the DNS server is associated with Tomcat, so my development deployed on JBoss can only be accessed through IP address.
My team and I spoke to the company in charge of the DNS server and it indicated that Tomcat's configuration as DNS response should be made by us, given that this company is only in charge of redirecting the IP without specifying the web server.
In order to solve this problem I have two proposals which I don't know how to implement:
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2. Deploy the application made on JBoss on Tomcat server.
I would really appreciate your help with any of these proposals. It is a very important matter for the company.
Thanks a lot beforehand for your help.

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The below snapshot shows the issue.
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I did the same thing just as I for apache server, except that I changed the listening port to something else. added that entry in the router. incorporated tomcat in eclipse and then started the sample project. using whatismyip.com, i got the ip address. i could access my webserver from elsewhere...

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