Here is the code of the server, i'll try to make a wireshark trace later.
public class ChatroomSipServlet extends SipServlet {
    public final static String USER_LIST = "userList";
    public final static String CHATROOM_SERVER_NAME = "chatroomservername";
    public String serverAddress;
    public SipFactory factory;
    @Override
    public void init(ServletConfig servletConfig) throws ServletException {
        super.init(servletConfig);
        System.out.println("Chatroom sip servlet is gestart!");
        try {
            factory = (SipFactory) getServletContext().getAttribute("javax.servlet.sip.SipFactory");
            System.out.println("Sip Factory: " + factory);
        } catch (Exception e) {
            throw new ServletException("Factory probleem!", e);
        }
        getServletContext().setAttribute(USER_LIST, new ArrayList<String>());
        serverAddress = getServletConfig().getInitParameter(CHATROOM_SERVER_NAME);
        System.out.println("serverAddress is: " + serverAddress);
    }
    @Override
    public void destroy() {
        try {
            sendToAll(serverAddress, "Server sluit af!");
        } catch (Throwable e) {
            e.printStackTrace();
        }
        super.destroy();
    }
    protected void doMessage(SipServletRequest request) throws ServletException, IOException {
        System.out.println(getDateTime() + " Bericht ontvangen");
        request.createResponse(SipServletResponse.SC_OK).send();
        String message = request.getContent().toString();
        String from = ((SipURI) request.getFrom().getURI()).toString();
        if (message.equalsIgnoreCase("/quit")) {
            sendToUser(from, "Bye");
            removeUser(from);
            return;
        }
        if (!containsUser(from)) {
            sendToUser(from, "Welkom in de chatroom. Typ '/quit' om af te sluiten.");
            addUser(from);
        }
        if (message.equalsIgnoreCase("/who")) {
            String users = "Lijst van de gebruikers:\n";
            List<String> list = (List<String>) getServletContext().getAttribute(USER_LIST);
            for (String user : list) {
                users += user + "\n";
            }
            sendToUser(from, users);
            return;
        }
        if (message.equalsIgnoreCase("/join")) {
            return;
        }
        sendToAll(from, message);
    }
    protected void doErrorResponse(SipServletResponse response) throws ServletException, IOException {
//      String receiver = response.getTo().toString();
        String receiver = ((SipURI) response.getTo().getURI()).toString();
        System.out.println(getDateTime() + " Errorresponse voor " + receiver);
        removeUser(receiver);
    }
    protected void doSuccessResponse(SipServletResponse response) throws ServletException, IOException {
        response.getApplicationSession().invalidate();
    }
    private void sendToAll(String from, String message) throws ServletParseException, IOException {
        List<String> list = (List<String>) getServletContext().getAttribute(USER_LIST);
        for (String user : list) {
            SipApplicationSession session = factory.createApplicationSession();
            System.out.println(getDateTime() + " Session created voor " + user);
            SipServletRequest request = factory.createRequest(session, "MESSAGE", serverAddress, user);
            String msg = from + " stuurt: \n" + message;
            request.setContent(msg.getBytes(), "text/plain");
            request.send();
        }
    }
    private void sendToUser(String to, String message) throws ServletParseException, IOException {
        SipApplicationSession session = factory.createApplicationSession();
        SipServletRequest request = factory.createRequest(session, "MESSAGE", serverAddress, to);
        request.setContent(message.getBytes(), "text/plain");
        request.send();
    }
    private boolean containsUser(String from) {
        List<String> list = (List<String>) getServletContext().getAttribute(USER_LIST);
        return list.contains(from);
    }
    private void addUser(String from) {
        List<String> list = (List<String>) getServletContext().getAttribute(USER_LIST);
        list.add(from);
    }
    private void removeUser(String from) {
        System.out.println(getDateTime() + " " + from + " wordt verwijderd uit de lijst.");
        List<String> list = (List<String>) getServletContext().getAttribute(USER_LIST);
        list.remove(from);
    }
    @Override
    protected void doRegister(SipServletRequest req) throws ServletException, IOException {
        System.out.println("Register request ontvangen: " + req.getTo());
        int response = SipServletResponse.SC_OK;
        SipServletResponse resp = req.createResponse(response);
        resp.send();
    }
    private String getDateTime() {
        DateFormat dateFormat = new SimpleDateFormat("[" + "HH:mm:ss" + "]");
        Date date = new Date();
        return dateFormat.format(date);
    }
}
And the sip.xml
<sip-app>
    <app-name>sip.chatvoorbeeld.ChatServer</app-name>
    <display-name>Chatroom Sip Servlet</display-name>
    <description>Chatroom Sip Servlet</description>
    <servlet-selection>
        <main-servlet>
            ChatroomSipServlet
        </main-servlet>
    </servlet-selection>
    <session-config>
        <session-timeout>5</session-timeout>
    </session-config>
    <servlet>
        <servlet-name>ChatroomSipServlet</servlet-name>
        <display-name>ChatroomSipServlet</display-name>
        <description>Chatroom SIP servlet</description>
        <servlet-class>
            sip.chatvoorbeeld.ChatroomSipServlet
        </servlet-class>
        <init-param>
            <param-name>chatroomservername</param-name>
            <param-value>sip:[email protected]:5060</param-value>
        </init-param>
        <load-on-startup>1</load-on-startup>
    </servlet>
</sip-app>
I also tried an empty servlet, just with a doMessage() method that just prints out "message received". Same 32 seconds delay...
Wireshark gives me:
I send the message "test" to the server:
MESSAGE sip:[email protected]:5060;transport=udp SIP/2.0
Call-ID: [email protected]
CSeq: 1 MESSAGE
From: "bobby" <sip:[email protected]:5095>;tag=textclientv1.0
To: "chatserver" <sip:[email protected]:5060>
Via: SIP/2.0/UDP 192.168.56.101:5095;branch=branch1
Max-Forwards: 70
Contact: "bobby" <sip:[email protected]:5095>
Content-Type: text/plain
Content-Length: 4
test
Server sends back:
SIP/2.0 200 OK
Content-Length: 0
To: "chatserver"<sip:[email protected]:5060>;tag=g9vdns7u-e
Cseq: 1 MESSAGE
Via: SIP/2.0/UDP 192.168.56.101:5095;branch=branch1
From: "bobby"<sip:[email protected]:5095>;tag=textclientv1.0
Call-Id: [email protected]
Server: Glassfish_SIP_2.0.0
MESSAGE sip:[email protected]:5095 SIP/2.0
Max-Forwards: 69
Content-Length: 43
To: <sip:[email protected]:5095>
Cseq: 1 MESSAGE
Via: SIP/2.0/UDP 192.168.56.1:5060;branch=z9hG4bKdaacb7673c871796474ca951221a6643db6c
Content-Type: text/plain
Call-Id: 192.168.56.1_11_6595680936174578736
From: <sip:[email protected]:5060>;tag=g9vdns7u-g
sip:[email protected]:5095 stuurt: 
test
Then my client again answers with an OK:
SIP/2.0 200 OK
To: <sip:[email protected]:5095>;tag=888
CSeq: 1 MESSAGE
Via: SIP/2.0/UDP 192.168.56.1:5060;branch=z9hG4bKdaacb7673c871796474ca951221a6643db6c;received=192.168.56.1
Call-ID: 192.168.56.1_11_6595680936174578736
From: <sip:[email protected]:5060>;tag=g9vdns7u-g
Content-Length: 0
So far so good, everything works well.
But now I send a second message to the server "test2" and I get this:
Client to server:
MESSAGE sip:[email protected]:5060;transport=udp SIP/2.0
Call-ID: [email protected]
CSeq: 1 MESSAGE
From: "bobby" <sip:[email protected]:5095>;tag=textclientv1.0
To: "chatserver" <sip:[email protected]:5060>
Via: SIP/2.0/UDP 192.168.56.101:5095;branch=branch1
Max-Forwards: 70
Contact: "bobby" <sip:[email protected]:5095>
Content-Type: text/plain
Content-Length: 5
test2
Then the server does respond with:
SIP/2.0 200 OK
Content-Length: 0
To: "chatserver"<sip:[email protected]:5060>;tag=g9vdns7u-e
Cseq: 1 MESSAGE
Via: SIP/2.0/UDP 192.168.56.101:5095;branch=branch1
From: "bobby"<sip:[email protected]:5095>;tag=textclientv1.0
Call-Id: [email protected]
Server: Glassfish_SIP_2.0.0
But then the communication stops... I get a 200 OK, but the println() in my doMessage() method is not passed.