How can we migrate IIS apps to docker containers on a VM one at a time?

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We currently have an ASP.NET web site that gets deployed in IIS with several Web API services as individual apps under the web site. Additionally we stand up a VM per customer with all of our apps deployed on each VM using a sub domain to route customer specific traffic to the VM that is configured for their use. URLs are similar to those below.

https://OurAmazingCustomer.OurCleverDomain.com/app1/customers
https://OurAmazingCustomer.OurCleverDomain.com/app2/orders
https://OurAmazingCustomer.OurCleverDomain.com/app3/catalogs
https://OurAmazingCustomer.OurCleverDomain.com/app4/audits

How can we deploy, for example, app3 in a docker container without needing to change the url route, while app1, app2 and app4 remain deployed as code under IIS?

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