Sorry for the delay in response.

I created a new VM with Server 2025.

I didn't exactly recreate current environment because I didn't want to install 
versions with known vulnerabilities.  I got it as close as I could.  I am still 
having the same problem with sending email notifications.  Here is my current 
setup:

Firebird
        Original Server   3.0.4.33054
        New Server w/Latest Software   3.0.13.33818
        New Server w/Older Software   3.0.13.33818

Java
        Original Server   8
        New Server w/Latest Software   Microsoft JDK with Hotspot 11.0.23+9
        New Server w/Older Software   8

Apache Tomcat
        Original Server   9.0.16
        New Server w/Latest Software   10.1.8
        New Server w/Older Software   9.0.115

Here is the webpage of "errors" that comes up when I test:

HTTP Status 500 – Internal Server Error
Type Exception Report

Message An exception occurred processing [MainView.jsp] at line [85]

Description The server encountered an unexpected condition that prevented it 
from fulfilling the request.

Exception

org.apache.jasper.JasperException: An exception occurred processing 
[MainView.jsp] at line [85]

82:             response.sendRedirect("login.action?reason="
83:                             + sessionBeanId.getLoginStatus());
84:     } else {
85:             MainViewBeanId.initialize(request);
86:             //              MainViewBeanId.retrieveChanges(sessionBeanId);
87:             //              MainViewBeanId.retrieveTasks(sessionBeanId);
88:             //<body onLoad="return showDeletionMessage('<jsp:getProperty 
name="MainViewBeanId" property="deletionError"/>')">


Stacktrace:
        
org.apache.jasper.servlet.JspServletWrapper.handleJspException(JspServletWrapper.java:581)
        
org.apache.jasper.servlet.JspServletWrapper.service(JspServletWrapper.java:457)
        org.apache.jasper.servlet.JspServlet.serviceJspFile(JspServlet.java:349)
        org.apache.jasper.servlet.JspServlet.service(JspServlet.java:300)
        javax.servlet.http.HttpServlet.service(HttpServlet.java:623)
        org.apache.tomcat.websocket.server.WsFilter.doFilter(WsFilter.java:51)
        octane.Home.doGet(Home.java:314)
        javax.servlet.http.HttpServlet.service(HttpServlet.java:529)
        javax.servlet.http.HttpServlet.service(HttpServlet.java:623)
        org.apache.tomcat.websocket.server.WsFilter.doFilter(WsFilter.java:51)
Root Cause

javax.servlet.ServletException: java.lang.NoClassDefFoundError: 
com/sun/mail/util/MailLogger
        
org.apache.jasper.runtime.PageContextImpl.handlePageException(PageContextImpl.java:625)
        org.apache.jsp.MainView_jsp._jspService(MainView_jsp.java:293)
        org.apache.jasper.runtime.HttpJspBase.service(HttpJspBase.java:62)
        javax.servlet.http.HttpServlet.service(HttpServlet.java:623)
        
org.apache.jasper.servlet.JspServletWrapper.service(JspServletWrapper.java:438)
        org.apache.jasper.servlet.JspServlet.serviceJspFile(JspServlet.java:349)
        org.apache.jasper.servlet.JspServlet.service(JspServlet.java:300)
        javax.servlet.http.HttpServlet.service(HttpServlet.java:623)
        org.apache.tomcat.websocket.server.WsFilter.doFilter(WsFilter.java:51)
        octane.Home.doGet(Home.java:314)
        javax.servlet.http.HttpServlet.service(HttpServlet.java:529)
        javax.servlet.http.HttpServlet.service(HttpServlet.java:623)
        org.apache.tomcat.websocket.server.WsFilter.doFilter(WsFilter.java:51)
Root Cause

java.lang.NoClassDefFoundError: com/sun/mail/util/MailLogger
        javax.mail.Session.initLogger(Session.java:283)
        javax.mail.Session.<init>(Session.java:268)
        javax.mail.Session.getDefaultInstance(Session.java:378)
        octane.JobManager.sendSingleEmail(JobManager.java:242)
        octane.MainViewBean.initialize(MainViewBean.java:145)
        org.apache.jsp.MainView_jsp._jspService(MainView_jsp.java:232)
        org.apache.jasper.runtime.HttpJspBase.service(HttpJspBase.java:62)
        javax.servlet.http.HttpServlet.service(HttpServlet.java:623)
        
org.apache.jasper.servlet.JspServletWrapper.service(JspServletWrapper.java:438)
        org.apache.jasper.servlet.JspServlet.serviceJspFile(JspServlet.java:349)
        org.apache.jasper.servlet.JspServlet.service(JspServlet.java:300)
        javax.servlet.http.HttpServlet.service(HttpServlet.java:623)
        org.apache.tomcat.websocket.server.WsFilter.doFilter(WsFilter.java:51)
        octane.Home.doGet(Home.java:314)
        javax.servlet.http.HttpServlet.service(HttpServlet.java:529)
        javax.servlet.http.HttpServlet.service(HttpServlet.java:623)
        org.apache.tomcat.websocket.server.WsFilter.doFilter(WsFilter.java:51)
Note The full stack trace of the root cause is available in the server logs.

Apache Tomcat/9.0.115

-----Original Message-----
From: Sebastian Trost via users <[email protected]> 
Sent: Monday, March 2, 2026 1:16 PM
To: [email protected]
Cc: Sebastian Trost <[email protected]>
Subject: Re: Apache Tomcat 10 Issue

(Sorry for the previous empty mail)

On 2/27/26 15:49, Short, William J. wrote:
> Moving it to a new Windows Server and upgrading because of vulnerabilities in 
> Apache Tomcat 9.0.16.
>
> Java 8 to Microsoft JDK with Hotspot 11.0.23+9
>
> Apache Tomcat 9.0.16 to 10.1.8
>
Bill,

why are you moving to Tomcat 10 when Tomcat 9 isn't end of life yet? Did the 
vendor recommend Tomcat 10 with their application?

My advice would be to only change one thing at a time and then test it.

In your case:

1. Move your old working software stack to the new machine (old java, old 
tomcat, old everything) -> test it 2. Create a second tomcat 9 (download the 
latest one) directory next to the old working one, stop the old tomcat and copy 
everything from old-tomcat9/webapps to new-tomcat9/webapps. Also, check if any 
other file is present in the old tomcat (you already mentioned you a files.xml, 
etc). Also copy these files to the new tomcat directory. 
Maybe even check contents of files, they may have been changed in the old 
tomcat directory. Test it!
3. Update to java 11. Test it!

And so on.

Sebastian





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