I am still trying to figure out why guacamole is not working. I looked at the 
journalctl output, but found nothing suspicious (see below for startup journal 
messages). When I look at the output of journalctl after attempting to use 
guacamole from a browser (i.e., http://<server external dns name>:<external NAT 
port>/guacamole), there is nothing in the output from tomcat, guacamole or 
apache.

Can anyone more experienced than I see something that might give a clue what is 
going wrong? The response at the browser when attempting to access guacamole is:

Not Found

The requested URL was not found on this server.

Apache/2.4.29 (Ubuntu) Server at <DNS name> Port XXXXX

(I have changed the DNS name and external port number). Is it possible that 
guacamole is getting confused because the internal port seen by apache (i.e., 
4443) is not the internal port used by NAT (i.e., 443). Also, is it possible 
that the from address that tomcat sees is 127.0.01 might confuse it when 
responding to the request?

Journalctl output:

Dec 19 09:54:31 Mount tomcat9[2234]: NOTE: Picked up JDK_JAVA_OPTIONS:  
--add-opens=java.base/java.lang=ALL-UNNAMED 
--add-opens=java.base/java.io=ALL-UNNAMED 
--add-opens=java.rmi/sun.rmi.transport=ALL-UNNAMED
Dec 19 09:54:32 Mount tomcat9[2234]: Match [Server/Service/Engine/Host/Valve] 
failed to set property [remoteIpProxiesHeader] to [x-forwarded-by]
Dec 19 09:54:32 Mount tomcat9[2234]: Server version name:   Apache 
Tomcat/9.0.16 (Ubuntu)
Dec 19 09:54:32 Mount tomcat9[2234]: Server built:          Mar 29 2022 
15:05:11 UTC
Dec 19 09:54:32 Mount tomcat9[2234]: Server version number: 9.0.16.0
Dec 19 09:54:32 Mount tomcat9[2234]: OS Name:               Linux
Dec 19 09:54:32 Mount tomcat9[2234]: OS Version:            4.15.0-200-generic
Dec 19 09:54:32 Mount tomcat9[2234]: Architecture:          i386
Dec 19 09:54:32 Mount tomcat9[2234]: Java Home:             
/usr/lib/jvm/java-11-openjdk-i386
Dec 19 09:54:32 Mount tomcat9[2234]: JVM Version:           
11.0.17+8-post-Ubuntu-1ubuntu218.04
Dec 19 09:54:32 Mount tomcat9[2234]: JVM Vendor:            Ubuntu
Dec 19 09:54:32 Mount tomcat9[2234]: CATALINA_BASE:         /var/lib/tomcat9
Dec 19 09:54:32 Mount tomcat9[2234]: CATALINA_HOME:         /usr/share/tomcat9
Dec 19 09:54:32 Mount tomcat9[2234]: Command line argument: 
--add-opens=java.base/java.lang=ALL-UNNAMED
Dec 19 09:54:32 Mount tomcat9[2234]: Command line argument: 
--add-opens=java.base/java.io=ALL-UNNAMED
Dec 19 09:54:32 Mount tomcat9[2234]: Command line argument: 
--add-opens=java.rmi/sun.rmi.transport=ALL-UNNAMED
Dec 19 09:54:32 Mount tomcat9[2234]: Command line argument: 
-Djava.util.logging.config.file=/var/lib/tomcat9/conf/logging.properties
Dec 19 09:54:32 Mount tomcat9[2234]: Command line argument: 
-Djava.util.logging.manager=org.apache.juli.ClassLoaderLogManager
Dec 19 09:54:32 Mount tomcat9[2234]: Command line argument: 
-Djava.awt.headless=true
Dec 19 09:54:32 Mount tomcat9[2234]: Command line argument: -XX:+UseG1GC
Dec 19 09:54:32 Mount tomcat9[2234]: Command line argument: 
-Djdk.tls.ephemeralDHKeySize=2048
Dec 19 09:54:32 Mount tomcat9[2234]: Command line argument: 
-Djava.protocol.handler.pkgs=org.apache.catalina.webresources
Dec 19 09:54:32 Mount tomcat9[2234]: Command line argument: 
-Dorg.apache.catalina.security.SecurityListener.UMASK=0027
Dec 19 09:54:32 Mount tomcat9[2234]: Command line argument: 
-Dignore.endorsed.dirs=
Dec 19 09:54:32 Mount tomcat9[2234]: Command line argument: 
-Dcatalina.base=/var/lib/tomcat9
Dec 19 09:54:32 Mount tomcat9[2234]: Command line argument: 
-Dcatalina.home=/usr/share/tomcat9
Dec 19 09:54:32 Mount tomcat9[2234]: Command line argument: 
-Djava.io.tmpdir=/tmp
Dec 19 09:54:32 Mount tomcat9[2234]: Loaded APR based Apache Tomcat Native 
library [1.2.21] using APR version [1.6.3].
Dec 19 09:54:32 Mount tomcat9[2234]: APR capabilities: IPv6 [true], sendfile 
[true], accept filters [false], random [true].
Dec 19 09:54:32 Mount tomcat9[2234]: APR/OpenSSL configuration: useAprConnector 
[false], useOpenSSL [true]
Dec 19 09:54:32 Mount tomcat9[2234]: OpenSSL successfully initialized [OpenSSL 
1.1.1  11 Sep 2018]
Dec 19 09:54:32 Mount tomcat9[2234]: Initializing ProtocolHandler 
["http-nio-8080"]
Dec 19 09:54:32 Mount tomcat9[2234]: Server initialization in [1,056] 
milliseconds
Dec 19 09:54:32 Mount tomcat9[2234]: Starting service [Catalina]
Dec 19 09:54:32 Mount tomcat9[2234]: Starting Servlet engine: [Apache 
Tomcat/9.0.16 (Ubuntu)]
Dec 19 09:54:32 Mount tomcat9[2234]: Deploying deployment descriptor 
[/etc/tomcat9/Catalina/localhost/manager.xml]
Dec 19 09:54:32 Mount tomcat9[2234]: The path attribute with value [/manager] 
in deployment descriptor [/etc/tomcat9/Catalina/localhost/manager.xml] has been 
ignored
Dec 19 09:54:34 Mount tomcat9[2234]: At least one JAR was scanned for TLDs yet 
contained no TLDs. Enable debug logging for this logger for a complete list of 
JARs that were scanned but no TLDs were found in them. Skipping unneeded JARs 
during scanning can improve startup time and JSP compilation time.
Dec 19 09:54:34 Mount tomcat9[2234]: Deployment of deployment descriptor 
[/etc/tomcat9/Catalina/localhost/manager.xml] has finished in [1,843] ms
Dec 19 09:54:34 Mount tomcat9[2234]: Deploying deployment descriptor 
[/etc/tomcat9/Catalina/localhost/host-manager.xml]
Dec 19 09:54:34 Mount tomcat9[2234]: The path attribute with value 
[/host-manager] in deployment descriptor 
[/etc/tomcat9/Catalina/localhost/host-manager.xml] has been ignored
Dec 19 09:54:35 Mount tomcat9[2234]: At least one JAR was scanned for TLDs yet 
contained no TLDs. Enable debug logging for this logger for a complete list of 
JARs that were scanned but no TLDs were found in them. Skipping unneeded JARs 
during scanning can improve startup time and JSP compilation time.
Dec 19 09:54:35 Mount tomcat9[2234]: Deployment of deployment descriptor 
[/etc/tomcat9/Catalina/localhost/host-manager.xml] has finished in [1,029] ms
Dec 19 09:54:35 Mount tomcat9[2234]: Deploying web application archive 
[/var/lib/tomcat9/webapps/guacamole.war]
Dec 19 09:54:38 Mount tomcat9[2234]: At least one JAR was scanned for TLDs yet 
contained no TLDs. Enable debug logging for this logger for a complete list of 
JARs that were scanned but no TLDs were found in them. Skipping unneeded JARs 
during scanning can improve startup time and JSP compilation time.
Dec 19 09:54:38 Mount tomcat9[2234]: 09:54:38.315 [main] INFO  
o.a.g.environment.LocalEnvironment - GUACAMOLE_HOME is "/etc/guacamole".
Dec 19 09:54:38 Mount tomcat9[2234]: 09:54:38.441 [main] INFO  
o.a.g.rest.auth.HashTokenSessionMap - Sessions will expire after 60 minutes of 
inactivity.
Dec 19 09:54:38 Mount tomcat9[2234]: 09:54:38.673 [main] INFO  
o.a.g.environment.LocalEnvironment - GUACAMOLE_HOME is "/etc/guacamole".
Dec 19 09:54:40 Mount tomcat9[2234]: 09:54:40.421 [main] INFO  
o.a.g.extension.ExtensionModule - Extension "MySQL Authentication" loaded.
Dec 19 09:54:40 Mount tomcat9[2234]: 09:54:40.424 [main] INFO  
o.a.g.environment.LocalEnvironment - GUACAMOLE_HOME is "/etc/guacamole".
Dec 19 09:54:40 Mount tomcat9[2234]: 09:54:40.584 [main] INFO  
o.a.g.t.w.WebSocketTunnelModule - Loading JSR-356 WebSocket support...
Dec 19 09:54:41 Mount tomcat9[2234]: Registering 
org.apache.guacamole.rest.RESTExceptionMapper as a provider class
Dec 19 09:54:41 Mount tomcat9[2234]: Registering 
org.apache.guacamole.rest.extension.ExtensionRESTService as a root resource 
class
Dec 19 09:54:41 Mount tomcat9[2234]: Registering 
org.apache.guacamole.rest.language.LanguageRESTService as a root resource class
Dec 19 09:54:41 Mount tomcat9[2234]: Registering 
org.apache.guacamole.rest.patch.PatchRESTService as a root resource class
Dec 19 09:54:41 Mount tomcat9[2234]: Registering 
org.apache.guacamole.rest.auth.TokenRESTService as a root resource class
Dec 19 09:54:41 Mount tomcat9[2234]: Registering 
org.apache.guacamole.rest.session.SessionRESTService as a root resource class
Dec 19 09:54:41 Mount tomcat9[2234]: Registering 
org.codehaus.jackson.jaxrs.JacksonJsonProvider as a provider class
Dec 19 09:54:41 Mount tomcat9[2234]: Initiating Jersey application, version 
'Jersey: 1.17.1 02/28/2013 12:47 PM'
Dec 19 09:54:41 Mount tomcat9[2234]: Binding 
org.apache.guacamole.rest.RESTExceptionMapper to GuiceManagedComponentProvider 
with the scope "Singleton"
Dec 19 09:54:41 Mount tomcat9[2234]: Binding 
org.codehaus.jackson.jaxrs.JacksonJsonProvider to GuiceManagedComponentProvider 
with the scope "Singleton"
Dec 19 09:54:42 Mount tomcat9[2234]: Binding 
org.apache.guacamole.rest.extension.ExtensionRESTService to 
GuiceManagedComponentProvider with the scope "PerRequest"
Dec 19 09:54:42 Mount tomcat9[2234]: Binding 
org.apache.guacamole.rest.language.LanguageRESTService to 
GuiceManagedComponentProvider with the scope "PerRequest"
Dec 19 09:54:42 Mount tomcat9[2234]: Binding 
org.apache.guacamole.rest.patch.PatchRESTService to 
GuiceManagedComponentProvider with the scope "PerRequest"
Dec 19 09:54:42 Mount tomcat9[2234]: Binding 
org.apache.guacamole.rest.auth.TokenRESTService to 
GuiceManagedComponentProvider with the scope "PerRequest"
Dec 19 09:54:42 Mount tomcat9[2234]: Binding 
org.apache.guacamole.rest.session.SessionRESTService to 
GuiceManagedComponentProvider with the scope "PerRequest"
Dec 19 09:54:42 Mount tomcat9[2234]: WebjarsServlet initialization completed
Dec 19 09:54:42 Mount tomcat9[2234]: Deployment of web application archive 
[/var/lib/tomcat9/webapps/guacamole.war] has finished in [6,444] ms
Dec 19 09:54:42 Mount tomcat9[2234]: Deploying web application directory 
[/var/lib/tomcat9/webapps/ROOT]
Dec 19 09:54:43 Mount tomcat9[2234]: At least one JAR was scanned for TLDs yet 
contained no TLDs. Enable debug logging for this logger for a complete list of 
JARs that were scanned but no TLDs were found in them. Skipping unneeded JARs 
during scanning can improve startup time and JSP compilation time.
Dec 19 09:54:43 Mount tomcat9[2234]: Deployment of web application directory 
[/var/lib/tomcat9/webapps/ROOT] has finished in [1,042] ms
Dec 19 09:54:43 Mount tomcat9[2234]: Starting ProtocolHandler ["http-nio-8080"]
Dec 19 09:54:43 Mount tomcat9[2234]: Server startup in [10,492] milliseconds
(END)

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