ho provato lo stesso ad importare mail.jar e activation.jar, non presenti nella lib di tomcat, e risolve il problema legato a quanto detto precedentemente (Anche la guida di tomcat 6 dice di dover fare questa cosa). Ho aggiunto WEB-INF/web.xml con questo contenuto:

<?xml version="1.0" encoding="ISO-8859-1"?>
<!--
Licensed to the Apache Software Foundation (ASF) under one or more
contributor license agreements. See the NOTICE file distributed with
this work for additional information regarding copyright ownership.
The ASF licenses this file to You under the Apache License, Version 2.0
(the "License"); you may not use this file except in compliance with
the License. You may obtain a copy of the License at

http://www.apache.org/licenses/LICENSE-2.0

Unless required by applicable law or agreed to in writing, software
distributed under the License is distributed on an "AS IS" BASIS,
WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
See the License for the specific language governing permissions and
limitations under the License.
-->
<web-app xmlns="http://java.sun.com/xml/ns/javaee"
xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance"
xsi:schemaLocation="http://java.sun.com/xml/ns/javaee http://java.sun.com/xml/ns/javaee/web-app_2_5.xsd"
version="2.5">

<display-name>Tomcat Documentation</display-name>
<description>
Tomcat Documentation.
</description>


<resource-ref>
<description>
Resource reference to a factory for javax.mail.Session
instances that may be used for sending electronic mail
messages, preconfigured to connect to the appropriate
SMTP server.
</description>
<res-ref-name>
mail/Session
</res-ref-name>
<res-type>
javax.mail.Session
</res-type>
<res-auth>
Container
</res-auth>
</resource-ref>

</web-app>

Ma ancora niente: errore sempre identico :
com.sun.mail.smtp.SMTPSendFailedException: 530 5.7.0 Must issue a STARTTLS command first