Thanks. I'll do a few more tests. This is the debug log from my Seam App: | 17:39:34,635 INFO [MailSession] Creating JavaMail Session (mysmtpserver:587) | 17:39:34,641 INFO [STDOUT] DEBUG: setDebug: JavaMail version 1.4ea | 17:39:34,641 INFO [MailSession] connected to mail server | 17:39:34,666 INFO [STDOUT] DEBUG: getProvider() returning javax.mail.Provider[TRANSPORT,smtp,com.sun.mail.smtp.SMTPTransport,Sun Microsystems, Inc] | 17:39:34,668 INFO [STDOUT] DEBUG SMTP: useEhlo true, useAuth true | 17:39:34,668 INFO [STDOUT] DEBUG SMTP: useEhlo true, useAuth true | 17:39:34,668 INFO [STDOUT] DEBUG SMTP: trying to connect to host mysmtpserver", port 587, isSSL false | 17:39:35,046 INFO [STDOUT] 220 spunkymail-a14.g.dreamhost.com ESMTP | 17:39:35,046 INFO [STDOUT] DEBUG SMTP: connected to host "mysmtpserver", port: 587 | 17:39:35,047 INFO [STDOUT] EHLO myhostname.local | 17:39:35,222 INFO [STDOUT] 250-spunkymail-a14.g.dreamhost.com | 250-PIPELINING | 250-SIZE 40960000 | 250-ETRN | 250-STARTTLS | 250-AUTH LOGIN PLAIN | 250-AUTH=LOGIN PLAIN | 250 8BITMIME | 17:39:35,222 INFO [STDOUT] DEBUG SMTP: Found extension "PIPELINING", arg "" | 17:39:35,222 INFO [STDOUT] DEBUG SMTP: Found extension "SIZE", arg "40960000" | 17:39:35,222 INFO [STDOUT] DEBUG SMTP: Found extension "ETRN", arg "" | 17:39:35,222 INFO [STDOUT] DEBUG SMTP: Found extension "STARTTLS", arg "" | 17:39:35,223 INFO [STDOUT] DEBUG SMTP: Found extension "AUTH", arg "LOGIN PLAIN" | 17:39:35,223 INFO [STDOUT] DEBUG SMTP: Found extension "AUTH=LOGIN", arg "PLAIN" | 17:39:35,223 INFO [STDOUT] DEBUG SMTP: Found extension "8BITMIME", arg "" | 17:39:35,223 INFO [STDOUT] STARTTLS | 17:39:35,401 INFO [STDOUT] 220 Ready to start TLS | 17:39:35,402 INFO [STDOUT] EHLO myhostname.local | 17:39:35,595 ERROR [PasswordReset] Exception while sending Password reset email: Can't send command to SMTP host | And this is the debug log from my test harness using the same config: | DEBUG: JavaMail version 1.4ea | DEBUG: java.io.FileNotFoundException: /System/Library/Frameworks/JavaVM.framework/Versions/1.5.0/Home/lib/javamail.providers (No such file or directory) | DEBUG: !anyLoaded | DEBUG: not loading resource: /META-INF/javamail.providers | DEBUG: successfully loaded resource: /META-INF/javamail.default.providers | DEBUG: Tables of loaded providers | DEBUG: Providers Listed By Class Name: {com.sun.mail.smtp.SMTPSSLTransport=javax.mail.Provider[TRANSPORT,smtps,com.sun.mail.smtp.SMTPSSLTransport,Sun Microsystems, Inc], com.sun.mail.smtp.SMTPTransport=javax.mail.Provider[TRANSPORT,smtp,com.sun.mail.smtp.SMTPTransport,Sun Microsystems, Inc], com.sun.mail.imap.IMAPSSLStore=javax.mail.Provider[STORE,imaps,com.sun.mail.imap.IMAPSSLStore,Sun Microsystems, Inc], com.sun.mail.pop3.POP3SSLStore=javax.mail.Provider[STORE,pop3s,com.sun.mail.pop3.POP3SSLStore,Sun Microsystems, Inc], com.sun.mail.imap.IMAPStore=javax.mail.Provider[STORE,imap,com.sun.mail.imap.IMAPStore,Sun Microsystems, Inc], com.sun.mail.pop3.POP3Store=javax.mail.Provider[STORE,pop3,com.sun.mail.pop3.POP3Store,Sun Microsystems, Inc]} | DEBUG: Providers Listed By Protocol: {imaps=javax.mail.Provider[STORE,imaps,com.sun.mail.imap.IMAPSSLStore,Sun Microsystems, Inc], imap=javax.mail.Provider[STORE,imap,com.sun.mail.imap.IMAPStore,Sun Microsystems, Inc], smtps=javax.mail.Provider[TRANSPORT,smtps,com.sun.mail.smtp.SMTPSSLTransport,Sun Microsystems, Inc], pop3=javax.mail.Provider[STORE,pop3,com.sun.mail.pop3.POP3Store,Sun Microsystems, Inc], pop3s=javax.mail.Provider[STORE,pop3s,com.sun.mail.pop3.POP3SSLStore,Sun Microsystems, Inc], smtp=javax.mail.Provider[TRANSPORT,smtp,com.sun.mail.smtp.SMTPTransport,Sun Microsystems, Inc]} | DEBUG: successfully loaded resource: /META-INF/javamail.default.address.map | DEBUG: !anyLoaded | DEBUG: not loading resource: /META-INF/javamail.address.map | DEBUG: java.io.FileNotFoundException: /System/Library/Frameworks/JavaVM.framework/Versions/1.5.0/Home/lib/javamail.address.map (No such file or directory) | DEBUG: getProvider() returning javax.mail.Provider[TRANSPORT,smtp,com.sun.mail.smtp.SMTPTransport,Sun Microsystems, Inc] | DEBUG SMTP: useEhlo true, useAuth false | DEBUG SMTP: trying to connect to host "mysmtpserver", port 587, isSSL false | 220 spunkymail-a2.g.dreamhost.com ESMTP | DEBUG SMTP: connected to host "mysmtpserver", port: 587 | | EHLO myhostname.local | 250-spunkymail-a2.g.dreamhost.com | 250-PIPELINING | 250-SIZE 40960000 | 250-ETRN | 250-STARTTLS | 250-AUTH PLAIN LOGIN | 250-AUTH=PLAIN LOGIN | 250 8BITMIME | DEBUG SMTP: Found extension "PIPELINING", arg "" | DEBUG SMTP: Found extension "SIZE", arg "40960000" | DEBUG SMTP: Found extension "ETRN", arg "" | DEBUG SMTP: Found extension "STARTTLS", arg "" | DEBUG SMTP: Found extension "AUTH", arg "PLAIN LOGIN" | DEBUG SMTP: Found extension "AUTH=PLAIN", arg "LOGIN" | DEBUG SMTP: Found extension "8BITMIME", arg "" | DEBUG SMTP: use8bit false | MAIL FROM:<test@mysmtpserver> | 250 Ok | RCPT TO:<test@myemail.com> | 250 Ok | DEBUG SMTP: Verified Addresses | DEBUG SMTP: test@mysmtpserver | DATA | 354 End data with <CR><LF>.<CR><LF> | To: test(a)myemail.com | Message-ID: <14732323.01178728958895.JavaMail.test@mysmtpserver> | Subject: Testing javamail plain | MIME-Version: 1.0 | Content-Type: text/plain; charset=us-ascii | Content-Transfer-Encoding: 7bit | | This is a test at Wed May 09 17:42:37 BST 2007 | . | 250 Ok: queued as 4DB0E87CAF | QUIT | 221 Bye | View the original post : http://www.jboss.com/index.html?module=bb&op=viewtopic&p=4044485#... 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