Smtp sender restrictions question

I have the following in my main.cf file for sender restrictions. permitsasl_authenticated,permit_mynetworks,rejectn onfqdnsender,permit
Seems pretty standard, but I have had some students in my district send emails to teachers as [email protected] Now the first thing I am going to do is take the building ip ranges out of the mynetworks and require sasl on all email clients. I think this will stop this from happening.
My question is can a student send an email as a bogus user to someone from mydomain if they don't have some way of sasl authentication? I remember in the past that when my teachers were at home and they would send emails they could send to each other mydomain to mydomain but not outside, mydomain to yahoo.com for example.
So they were not using sasl or mynetworks because they were using their home ip. If that would still be allowed, what can I do.
Thanks for any clarifications!
JL
Mac OS X (10.4.8)

I was a little confused by your question, so this may
sound like more of a "buck-shot" approach to your
problem than you would like. I apologize if this
doesn't answer your question directly. However, if I
were you, I would implement Pterobyte's "Frontline
spam defense for Mac OS X Server" located at
http://osx.topicdesk.com/downloads
I have enabled this, it is excellent.
In this PDF file, Pterobyte provides a set of
restrictions for main.cf that optimizes Postfix's
abilities to deal with unwanted mail up-front before
it reaches your content filter.
Concerning your question specifically, are you saying
that a student can send mail using your mail server
without authenticating as long as they are sending to
another user on the server and claiming to have an
email address originating from your TLD?
I believe the student is using terminal or something similar on some of our less restricted osx laptops, he is then sending emails to users in my domain. If I remove the ip range from the building he is in, will it stop him from sending emails? He is making up a return address like [email protected] and sending to [email protected] He might even be using php, but I only want email to go to any user local or not, from the district, if they have set my server requires authentication in an email client.
Will removing the ip be enough to stop this?
Thanks!
JL

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I'm stucked with smtp authentication in a project.
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It seems that only the half of the authentication process could be successful, as the server accepts EHLO, but when it switches to secure the program fails with the exception:
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public void SendMail() throws Exception{
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I'll copy the full message below:
+2010.06.29. 12:03:10 mailapi_2.Main main+
SEVERE: null
javax.mail.MessagingException: Could not convert socket to TLS;+
nested exception is:
javax.net.ssl.SSLHandshakeException: sun.security.validator.ValidatorException: PKIX path building failed: sun.security.provider.certpath.SunCertPathBuilderException: unable to find valid certification path to requested target
at com.sun.mail.smtp.SMTPTransport.startTLS(SMTPTransport.java:1652)
at com.sun.mail.smtp.SMTPTransport.protocolConnect(SMTPTransport.java:534)
at javax.mail.Service.connect(Service.java:291)
at mailapi_2.SimpleMail.SendMail1(SimpleMail.java:59)
at mailapi_2.Main.main(Main.java:23)
Caused by: javax.net.ssl.SSLHandshakeException: sun.security.validator.ValidatorException: PKIX path building failed: sun.security.provider.certpath.SunCertPathBuilderException: unable to find valid certification path to requested target
at com.sun.net.ssl.internal.ssl.Alerts.getSSLException(Alerts.java:174)
at com.sun.net.ssl.internal.ssl.SSLSocketImpl.fatal(SSLSocketImpl.java:1591)
at com.sun.net.ssl.internal.ssl.Handshaker.fatalSE(Handshaker.java:187)
at com.sun.net.ssl.internal.ssl.Handshaker.fatalSE(Handshaker.java:181)
at com.sun.net.ssl.internal.ssl.ClientHandshaker.serverCertificate(ClientHandshaker.java:1035)
at com.sun.net.ssl.internal.ssl.ClientHandshaker.processMessage(ClientHandshaker.java:124)
at com.sun.net.ssl.internal.ssl.Handshaker.processLoop(Handshaker.java:516)
at com.sun.net.ssl.internal.ssl.Handshaker.process_record(Handshaker.java:454)
at com.sun.net.ssl.internal.ssl.SSLSocketImpl.readRecord(SSLSocketImpl.java:884)
at com.sun.net.ssl.internal.ssl.SSLSocketImpl.performInitialHandshake(SSLSocketImpl.java:1096)
at com.sun.net.ssl.internal.ssl.SSLSocketImpl.startHandshake(SSLSocketImpl.java:1123)
at com.sun.net.ssl.internal.ssl.SSLSocketImpl.startHandshake(SSLSocketImpl.java:1107)
at com.sun.mail.util.SocketFetcher.configureSSLSocket(SocketFetcher.java:503)
at com.sun.mail.util.SocketFetcher.startTLS(SocketFetcher.java:443)
at com.sun.mail.smtp.SMTPTransport.startTLS(SMTPTransport.java:1647)
+... 4 more+
Caused by: sun.security.validator.ValidatorException: PKIX path building failed: sun.security.provider.certpath.SunCertPathBuilderException: unable to find valid certification path to requested target
at sun.security.validator.PKIXValidator.doBuild(PKIXValidator.java:285)
at sun.security.validator.PKIXValidator.engineValidate(PKIXValidator.java:191)
at sun.security.validator.Validator.validate(Validator.java:218)
at com.sun.net.ssl.internal.ssl.X509TrustManagerImpl.validate(X509TrustManagerImpl.java:126)
at com.sun.net.ssl.internal.ssl.X509TrustManagerImpl.checkServerTrusted(X509TrustManagerImpl.java:209)
Could not convert socket to TLS
at com.sun.net.ssl.internal.ssl.X509TrustManagerImpl.checkServerTrusted(X509TrustManagerImpl.java:249)
at com.sun.net.ssl.internal.ssl.ClientHandshaker.serverCertificate(ClientHandshaker.java:1014)
+... 14 more+
Caused by: sun.security.provider.certpath.SunCertPathBuilderException: unable to find valid certification path to requested target
at sun.security.provider.certpath.SunCertPathBuilder.engineBuild(SunCertPathBuilder.java:174)
at java.security.cert.CertPathBuilder.build(CertPathBuilder.java:238)
at sun.security.validator.PKIXValidator.doBuild(PKIXValidator.java:280)
+... 20 more+
And the output panel before the exception:
Sending mail...
DEBUG: setDebug: JavaMail version 1.4.3
+DEBUG: getProvider() returning javax.mail.Provider[TRANSPORT,smtp,com.sun.mail.smtp.SMTPTransport,Sun Microsystems, Inc]+
DEBUG SMTP: useEhlo true, useAuth true
DEBUG SMTP: trying to connect to host "smtpserver", port 587, isSSL false
+220 exch.plt.local Microsoft ESMTP MAIL Service ready at Tue, 29 Jun 2010 12:03:08 +0200+
DEBUG SMTP: connected to host "smtpserver", port: 587
EHLO machine.codomain.local
+250-smtpserver.codomain.local Hello [xxx.xxx.xxx.xxx]+
+250-SIZE 15728640+
+250-PIPELINING+
+250-DSN+
+250-ENHANCEDSTATUSCODES+
+250-STARTTLS+
+250-AUTH GSSAPI NTLM+
+250-8BITMIME+
+250-BINARYMIME+
+250 CHUNKING+
DEBUG SMTP: Found extension "SIZE", arg "15728640"
DEBUG SMTP: Found extension "PIPELINING", arg ""
DEBUG SMTP: Found extension "DSN", arg ""
DEBUG SMTP: Found extension "ENHANCEDSTATUSCODES", arg ""
DEBUG SMTP: Found extension "STARTTLS", arg ""
DEBUG SMTP: Found extension "AUTH", arg "GSSAPI NTLM"
DEBUG SMTP: Found extension "8BITMIME", arg ""
DEBUG SMTP: Found extension "BINARYMIME", arg ""
DEBUG SMTP: Found extension "CHUNKING", arg ""
STARTTLS
+220 2.0.0 SMTP server ready+

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