(old style) Web Server is basically a WorkManager Client.
In fact, you can start a WorkManager Client with certain options and it will operate as WebServer (with command line and tracing capabilities).
However, good old WorkManager is of course not able to deal with https.
The same is true for all the other executables having a HTTP interface - Database Server, File Server, License Server.
Only the Webservices can be configured to use https since they are based on Apache technology.
The only way to use https for the "classic products" is to add a "proxy" in front of the products that support http only.
There are documented scenarios how a add a reverse proxy for Windchill:
- Users within the intranet access Windchill via HTTP
- Users outside (in the WAN) access Windchill via HTTPS through a reverse proxy