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  • Redirecting or routing all traffic to OpenVPN on a Mac OS X client

    - by sdr56p
    I have configured an OpenVPN (2.2.1) server on an Ubuntu virtual machine in the Amazon elastic compute cloud. The server is up and running. I have installed OpenVPN (2.2.1) on a Mac OS X (10.8.2) client and I am using the openvpn2 binary to connect (in opposition to other clients like Tunnelblick or Viscosity). I can connect with the client and successfully ping or ssh the server through the tunnel. However, I can't redirect all internet traffic through the VPN even if I use the push "redirect-gateway def1 bypass-dhcp" option in the server.conf configurations. When I connect to the server with these configurations, I get a successful connection, but then an infinite series of error messages: "write UDPv4: No route to host (code=65)". Traffic routing seems to be compromised because I am not able to access anything anymore, not even the OpenVPN server (by pinging 10.8.0.1 for instance). This is beyond me. I am finding little help on the web and don't know what to try next. I don't think it is a problem of forwarding the traffic on the server since, first, I have also took care of that and, second, I can't even ping the VPN server locally through the tunnel (or ping anything at all for that matter). Thank you for your help. Here is the server.conf. file: port 1194 proto udp dev tun ca ca.crt cert ec2-server.crt key ec2-server.key # This file should be kept secret dh dh1024.pem server 10.8.0.0 255.255.255.0 ifconfig-pool-persist ipp.txt push "redirect-gateway def1 bypass-dhcp" client-to-client keepalive 10 120 comp-lzo persist-key persist-tun status openvpn-status.log verb 3 And the client.conf file: client dev tun proto udp remote servername.com 1194 resolv-retry infinite nobind persist-key persist-tun ca ca.crt cert Toto5.crt key Toto5.key ns-cert-type server comp-lzo verb 3 Here is the connection log with the error messages: $ sudo openvpn2 --config client.conf Wed Mar 13 22:58:22 2013 OpenVPN 2.2.1 x86_64-apple-darwin12.2.0 [SSL] [LZO2] [eurephia] built on Mar 4 2013 Wed Mar 13 22:58:22 2013 NOTE: OpenVPN 2.1 requires '--script-security 2' or higher to call user-defined scripts or executables Wed Mar 13 22:58:22 2013 LZO compression initialized Wed Mar 13 22:58:22 2013 Control Channel MTU parms [ L:1542 D:138 EF:38 EB:0 ET:0 EL:0 ] Wed Mar 13 22:58:22 2013 Socket Buffers: R=[196724->65536] S=[9216->65536] Wed Mar 13 22:58:22 2013 Data Channel MTU parms [ L:1542 D:1450 EF:42 EB:135 ET:0 EL:0 AF:3/1 ] Wed Mar 13 22:58:22 2013 Local Options hash (VER=V4): '41690919' Wed Mar 13 22:58:22 2013 Expected Remote Options hash (VER=V4): '530fdded' Wed Mar 13 22:58:22 2013 UDPv4 link local: [undef] Wed Mar 13 22:58:22 2013 UDPv4 link remote: 54.234.43.171:1194 Wed Mar 13 22:58:22 2013 TLS: Initial packet from 54.234.43.171:1194, sid=ffbaf343 d0c1a266 Wed Mar 13 22:58:22 2013 VERIFY OK: depth=1, /C=US/ST=CA/L=SanFrancisco/O=Fort-Funst ... ost.domain Wed Mar 13 22:58:22 2013 VERIFY OK: nsCertType=SERVER Wed Mar 13 22:58:22 2013 VERIFY OK: depth=0, /C=US/ST=CA/L=SanFrancisco/O=Fort-Funst ... ost.domain Wed Mar 13 22:58:23 2013 Data Channel Encrypt: Cipher 'BF-CBC' initialized with 128 bit key Wed Mar 13 22:58:23 2013 Data Channel Encrypt: Using 160 bit message hash 'SHA1' for HMAC authentication Wed Mar 13 22:58:23 2013 Data Channel Decrypt: Cipher 'BF-CBC' initialized with 128 bit key Wed Mar 13 22:58:23 2013 Data Channel Decrypt: Using 160 bit message hash 'SHA1' for HMAC authentication Wed Mar 13 22:58:23 2013 Control Channel: TLSv1, cipher TLSv1/SSLv3 DHE-RSA-AES256-SHA, 1024 bit RSA Wed Mar 13 22:58:23 2013 [ec2-server] Peer Connection Initiated with 54.234.43.171:1194 Wed Mar 13 22:58:25 2013 SENT CONTROL [ec2-server]: 'PUSH_REQUEST' (status=1) Wed Mar 13 22:58:25 2013 PUSH: Received control message: 'PUSH_REPLY,route 10.8.0.0 255.255.255.0,topology net30,ping 10,ping-restart 120,ifconfig 10.8.0.6 10.8.0.5' Wed Mar 13 22:58:25 2013 OPTIONS IMPORT: timers and/or timeouts modified Wed Mar 13 22:58:25 2013 OPTIONS IMPORT: --ifconfig/up options modified Wed Mar 13 22:58:25 2013 OPTIONS IMPORT: route options modified Wed Mar 13 22:58:25 2013 ROUTE default_gateway=0.0.0.0 Wed Mar 13 22:58:25 2013 TUN/TAP device /dev/tun0 opened Wed Mar 13 22:58:25 2013 /sbin/ifconfig tun0 delete ifconfig: ioctl (SIOCDIFADDR): Can't assign requested address Wed Mar 13 22:58:25 2013 NOTE: Tried to delete pre-existing tun/tap instance -- No Problem if failure Wed Mar 13 22:58:25 2013 /sbin/ifconfig tun0 10.8.0.6 10.8.0.5 mtu 1500 netmask 255.255.255.255 up Wed Mar 13 22:58:25 2013 /sbin/route add -net 10.8.0.0 10.8.0.5 255.255.255.0 add net 10.8.0.0: gateway 10.8.0.5 Wed Mar 13 22:58:25 2013 Initialization Sequence Completed ^CWed Mar 13 22:58:30 2013 event_wait : Interrupted system call (code=4) Wed Mar 13 22:58:30 2013 TCP/UDP: Closing socket Wed Mar 13 22:58:30 2013 /sbin/route delete -net 10.8.0.0 10.8.0.5 255.255.255.0 delete net 10.8.0.0: gateway 10.8.0.5 Wed Mar 13 22:58:30 2013 Closing TUN/TAP interface Wed Mar 13 22:58:30 2013 SIGINT[hard,] received, process exiting toto5:ttntec2 Dominic$ sudo openvpn2 --config client.conf --remote ec2-54-234-43-171.compute-1.amazonaws.com Wed Mar 13 22:58:57 2013 OpenVPN 2.2.1 x86_64-apple-darwin12.2.0 [SSL] [LZO2] [eurephia] built on Mar 4 2013 Wed Mar 13 22:58:57 2013 NOTE: OpenVPN 2.1 requires '--script-security 2' or higher to call user-defined scripts or executables Wed Mar 13 22:58:57 2013 LZO compression initialized Wed Mar 13 22:58:57 2013 Control Channel MTU parms [ L:1542 D:138 EF:38 EB:0 ET:0 EL:0 ] Wed Mar 13 22:58:57 2013 Socket Buffers: R=[196724->65536] S=[9216->65536] Wed Mar 13 22:58:57 2013 Data Channel MTU parms [ L:1542 D:1450 EF:42 EB:135 ET:0 EL:0 AF:3/1 ] Wed Mar 13 22:58:57 2013 Local Options hash (VER=V4): '41690919' Wed Mar 13 22:58:57 2013 Expected Remote Options hash (VER=V4): '530fdded' Wed Mar 13 22:58:57 2013 UDPv4 link local: [undef] Wed Mar 13 22:58:57 2013 UDPv4 link remote: 54.234.43.171:1194 Wed Mar 13 22:58:57 2013 TLS: Initial packet from 54.234.43.171:1194, sid=a0d75468 ec26de14 Wed Mar 13 22:58:58 2013 VERIFY OK: depth=1, /C=US/ST=CA/L=SanFrancisco/O=Fort-Funst ... ost.domain Wed Mar 13 22:58:58 2013 VERIFY OK: nsCertType=SERVER Wed Mar 13 22:58:58 2013 VERIFY OK: depth=0, /C=US/ST=CA/L=SanFrancisco/O=Fort-Funst ... ost.domain Wed Mar 13 22:58:58 2013 Data Channel Encrypt: Cipher 'BF-CBC' initialized with 128 bit key Wed Mar 13 22:58:58 2013 Data Channel Encrypt: Using 160 bit message hash 'SHA1' for HMAC authentication Wed Mar 13 22:58:58 2013 Data Channel Decrypt: Cipher 'BF-CBC' initialized with 128 bit key Wed Mar 13 22:58:58 2013 Data Channel Decrypt: Using 160 bit message hash 'SHA1' for HMAC authentication Wed Mar 13 22:58:58 2013 Control Channel: TLSv1, cipher TLSv1/SSLv3 DHE-RSA-AES256-SHA, 1024 bit RSA Wed Mar 13 22:58:58 2013 [ec2-server] Peer Connection Initiated with 54.234.43.171:1194 Wed Mar 13 22:59:00 2013 SENT CONTROL [ec2-server]: 'PUSH_REQUEST' (status=1) Wed Mar 13 22:59:00 2013 PUSH: Received control message: 'PUSH_REPLY,redirect-gateway def1 bypass-dhcp,route 10.8.0.0 255.255.255.0,topology net30,ping 10,ping-restart 120,ifconfig 10.8.0.6 10.8.0.5' Wed Mar 13 22:59:00 2013 OPTIONS IMPORT: timers and/or timeouts modified Wed Mar 13 22:59:00 2013 OPTIONS IMPORT: --ifconfig/up options modified Wed Mar 13 22:59:00 2013 OPTIONS IMPORT: route options modified Wed Mar 13 22:59:00 2013 ROUTE default_gateway=0.0.0.0 Wed Mar 13 22:59:00 2013 TUN/TAP device /dev/tun0 opened Wed Mar 13 22:59:00 2013 /sbin/ifconfig tun0 delete ifconfig: ioctl (SIOCDIFADDR): Can't assign requested address Wed Mar 13 22:59:00 2013 NOTE: Tried to delete pre-existing tun/tap instance -- No Problem if failure Wed Mar 13 22:59:00 2013 /sbin/ifconfig tun0 10.8.0.6 10.8.0.5 mtu 1500 netmask 255.255.255.255 up Wed Mar 13 22:59:00 2013 /sbin/route add -net 54.234.43.171 0.0.0.0 255.255.255.255 add net 54.234.43.171: gateway 0.0.0.0 Wed Mar 13 22:59:00 2013 /sbin/route add -net 0.0.0.0 10.8.0.5 128.0.0.0 add net 0.0.0.0: gateway 10.8.0.5 Wed Mar 13 22:59:00 2013 /sbin/route add -net 128.0.0.0 10.8.0.5 128.0.0.0 add net 128.0.0.0: gateway 10.8.0.5 Wed Mar 13 22:59:00 2013 /sbin/route add -net 10.8.0.0 10.8.0.5 255.255.255.0 add net 10.8.0.0: gateway 10.8.0.5 Wed Mar 13 22:59:00 2013 Initialization Sequence Completed Wed Mar 13 22:59:00 2013 write UDPv4: No route to host (code=65) Wed Mar 13 22:59:00 2013 write UDPv4: No route to host (code=65) Wed Mar 13 22:59:01 2013 write UDPv4: No route to host (code=65) Wed Mar 13 22:59:01 2013 write UDPv4: No route to host (code=65) Wed Mar 13 22:59:01 2013 write UDPv4: No route to host (code=65) Wed Mar 13 22:59:02 2013 write UDPv4: No route to host (code=65) Wed Mar 13 22:59:02 2013 write UDPv4: No route to host (code=65) Wed Mar 13 22:59:02 2013 write UDPv4: No route to host (code=65) Wed Mar 13 22:59:02 2013 write UDPv4: No route to host (code=65) Wed Mar 13 22:59:02 2013 write UDPv4: No route to host (code=65) ... The routing table after a connection WITHOUT the push redirect-gateway (all traffic is not redirected to the VPN and everything is working fine, I can ping or ssh the OpenVPN server and access all other Internet resources through my default gateway): Destination Gateway Flags Refs Use Netif Expire default user148-1.wireless UGSc 50 0 en1 10.8/24 10.8.0.5 UGSc 2 7 tun0 10.8.0.5 10.8.0.6 UH 3 2 tun0 127 localhost UCS 0 0 lo0 localhost localhost UH 6 6692 lo0 client.openvpn.net client.openvpn.net UH 3 18 lo0 142.1.148/22 link#5 UCS 2 0 en1 user148-1.wireless 0:90:b:27:10:71 UHLWIir 50 0 en1 76 user150-173.wirele localhost UHS 0 0 lo0 142.1.151.255 ff:ff:ff:ff:ff:ff UHLWbI 0 2 en1 169.254 link#5 UCS 1 0 en1 169.254.255.255 0:90:b:27:10:71 UHLSWi 0 0 en1 71 The routing table after a connection with the push redirect-gateway option enable as in the server.conf file above (all internet traffic should be redirected to the VPN tunnel, but nothing is working, I can't access any Internet ressources at all): Destination Gateway Flags Refs Use Netif Expire 0/1 10.8.0.5 UGSc 1 0 tun0 default user148-1.wireless UGSc 7 0 en1 10.8/24 10.8.0.5 UGSc 0 0 tun0 10.8.0.5 10.8.0.6 UHr 6 0 tun0 54.234.43.171/32 0.0.0.0 UGSc 1 0 en1 127 localhost UCS 0 0 lo0 localhost localhost UH 3 6698 lo0 client.openvpn.net client.openvpn.net UH 0 27 lo0 128.0/1 10.8.0.5 UGSc 2 0 tun0 142.1.148/22 link#5 UCS 1 0 en1 user148-1.wireless 0:90:b:27:10:71 UHLWIir 1 0 en1 833 user150-173.wirele localhost UHS 0 0 lo0 169.254 link#5 UCS 1 0 en1 169.254.255.255 0:90:b:27:10:71 UHLSW 0 0 en1

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  • JavaMail not sending Subject or From under jetty:run-war

    - by Jason Thrasher
    Has anyone seen JavaMail not sending proper MimeMessages to an SMTP server, depending on how the JVM in started? At the end of the day, I can't send JavaMail SMTP messages with Subject: or From: fields, and it appears other headers are missing, only when running the app as a war. The web project is built with Maven and I'm testing sending JavaMail using a browser and a simple mail.jsp to debug and see different behavior when launching the app with: 1) mvn jetty:run (mail sends fine, with proper Subject and From fields) 2) mvn jetty:run-war (mail sends fine, but missing Subject, From, and other fields) I've meticulously run diff on the (verbose) Maven debug output (-X), and there are zero differences in the runtime dependencies between the two. I've also compared System properties, and they are identical. Something else is happening the jetty:run-war case that changes the way JavaMail behaves. What other stones need turning? Curiously, I've tried a debugger in both situations and found that the javax.mail.internet.MimeMessage instance is getting created differently. The webapp is using Spring to send email picked off of an Apache ActiveMQ queue. When running the app as mvn jetty:run the MimeMessage.contentStream variable is used for message content. When running as mvn jetty:run-war, the MimeMessage.content variable is used for the message contents, and the content = ASCIIUtility.getBytes(is); call removes all of the header data from the parsed content. Since this seemed very odd, and debugging Spring/ActiveMQ is a deep dive, I created a simplified test without any of that infrastructure: just a JSP using mail-1.4.2.jar, yet the same headers are missing. Also of note, these headers are missing when running the WAR file under Tomcat 5.5.27. Tomcat behaves just like Jetty when running the WAR, with the same missing headers. With JavaMail debugging turned on, I clearly see different output. GOOD CASE: In the jetty:run (non-WAR) the log output is: DEBUG: JavaMail version 1.4.2 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: 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 "mail.authsmtp.com", port 465, isSSL false 220 mail.authsmtp.com ESMTP Sendmail 8.14.2/8.14.2/Kp; Thu, 18 Jun 2009 01:35:24 +0100 (BST) DEBUG SMTP: connected to host "mail.authsmtp.com", port: 465 EHLO jmac.local 250-mail.authsmtp.com Hello sul-pubs-3a.Stanford.EDU [171.66.201.2], pleased to meet you 250-ENHANCEDSTATUSCODES 250-PIPELINING 250-8BITMIME 250-SIZE 52428800 250-AUTH CRAM-MD5 DIGEST-MD5 LOGIN PLAIN 250-DELIVERBY 250 HELP DEBUG SMTP: Found extension "ENHANCEDSTATUSCODES", arg "" DEBUG SMTP: Found extension "PIPELINING", arg "" DEBUG SMTP: Found extension "8BITMIME", arg "" DEBUG SMTP: Found extension "SIZE", arg "52428800" DEBUG SMTP: Found extension "AUTH", arg "CRAM-MD5 DIGEST-MD5 LOGIN PLAIN" DEBUG SMTP: Found extension "DELIVERBY", arg "" DEBUG SMTP: Found extension "HELP", arg "" DEBUG SMTP: Attempt to authenticate DEBUG SMTP: check mechanisms: LOGIN PLAIN DIGEST-MD5 AUTH LOGIN 334 VXNlcm5hjbt7 YWM0MDkwhi== 334 UGFzc3dvjbt7 YXV0aHNtdHAydog3 235 2.0.0 OK Authenticated DEBUG SMTP: use8bit false MAIL FROM:<[email protected]> 250 2.1.0 <[email protected]>... Sender ok RCPT TO:<[email protected]> 250 2.1.5 <[email protected]>... Recipient ok DEBUG SMTP: Verified Addresses DEBUG SMTP: Jason Thrasher <[email protected]> DATA 354 Enter mail, end with "." on a line by itself From: Webmaster <[email protected]> To: Jason Thrasher <[email protected]> Message-ID: <[email protected]> Subject: non-Spring: Hello World MIME-Version: 1.0 Content-Type: text/plain;charset=UTF-8 Content-Transfer-Encoding: 7bit Hello World: message body here . 250 2.0.0 n5I0ZOkD085654 Message accepted for delivery QUIT 221 2.0.0 mail.authsmtp.com closing connection BAD CASE: The log output when running as a WAR, with missing headers, is quite different: Loading javamail.default.providers from jar:file:/Users/jason/.m2/repository/javax/mail/mail/1.4.2/mail-1.4.2.jar!/META-INF/javamail.default.providers DEBUG: loading new provider protocol=imap, className=com.sun.mail.imap.IMAPStore, vendor=Sun Microsystems, Inc, version=null DEBUG: loading new provider protocol=imaps, className=com.sun.mail.imap.IMAPSSLStore, vendor=Sun Microsystems, Inc, version=null DEBUG: loading new provider protocol=smtp, className=com.sun.mail.smtp.SMTPTransport, vendor=Sun Microsystems, Inc, version=null DEBUG: loading new provider protocol=smtps, className=com.sun.mail.smtp.SMTPSSLTransport, vendor=Sun Microsystems, Inc, version=null DEBUG: loading new provider protocol=pop3, className=com.sun.mail.pop3.POP3Store, vendor=Sun Microsystems, Inc, version=null DEBUG: loading new provider protocol=pop3s, className=com.sun.mail.pop3.POP3SSLStore, vendor=Sun Microsystems, Inc, version=null Loading javamail.default.providers from jar:file:/Users/jason/Documents/dev/subscribeatron/software/trunk/web/struts/target/work/webapp/WEB-INF/lib/mail-1.4.2.jar!/META-INF/javamail.default.providers DEBUG: loading new provider protocol=imap, className=com.sun.mail.imap.IMAPStore, vendor=Sun Microsystems, Inc, version=null DEBUG: loading new provider protocol=imaps, className=com.sun.mail.imap.IMAPSSLStore, vendor=Sun Microsystems, Inc, version=null DEBUG: loading new provider protocol=smtp, className=com.sun.mail.smtp.SMTPTransport, vendor=Sun Microsystems, Inc, version=null DEBUG: loading new provider protocol=smtps, className=com.sun.mail.smtp.SMTPSSLTransport, vendor=Sun Microsystems, Inc, version=null DEBUG: loading new provider protocol=pop3, className=com.sun.mail.pop3.POP3Store, vendor=Sun Microsystems, Inc, version=null DEBUG: loading new provider protocol=pop3s, className=com.sun.mail.pop3.POP3SSLStore, vendor=Sun Microsystems, Inc, version=null DEBUG: getProvider() returning provider protocol=smtp; type=javax.mail.Provider$Type@98203f; class=com.sun.mail.smtp.SMTPTransport; vendor=Sun Microsystems, Inc DEBUG SMTP: useEhlo true, useAuth false DEBUG SMTP: trying to connect to host "mail.authsmtp.com", port 465, isSSL false 220 mail.authsmtp.com ESMTP Sendmail 8.14.2/8.14.2/Kp; Thu, 18 Jun 2009 01:51:46 +0100 (BST) DEBUG SMTP: connected to host "mail.authsmtp.com", port: 465 EHLO jmac.local 250-mail.authsmtp.com Hello sul-pubs-3a.Stanford.EDU [171.66.201.2], pleased to meet you 250-ENHANCEDSTATUSCODES 250-PIPELINING 250-8BITMIME 250-SIZE 52428800 250-AUTH CRAM-MD5 DIGEST-MD5 LOGIN PLAIN 250-DELIVERBY 250 HELP DEBUG SMTP: Found extension "ENHANCEDSTATUSCODES", arg "" DEBUG SMTP: Found extension "PIPELINING", arg "" DEBUG SMTP: Found extension "8BITMIME", arg "" DEBUG SMTP: Found extension "SIZE", arg "52428800" DEBUG SMTP: Found extension "AUTH", arg "CRAM-MD5 DIGEST-MD5 LOGIN PLAIN" DEBUG SMTP: Found extension "DELIVERBY", arg "" DEBUG SMTP: Found extension "HELP", arg "" DEBUG SMTP: Attempt to authenticate DEBUG SMTP: check mechanisms: LOGIN PLAIN DIGEST-MD5 AUTH LOGIN 334 VXNlcm5hjbt7 YWM0MDkwhi== 334 UGFzc3dvjbt7 YXV0aHNtdHAydog3 235 2.0.0 OK Authenticated DEBUG SMTP: use8bit false MAIL FROM:<[email protected]> 250 2.1.0 <[email protected]>... Sender ok RCPT TO:<[email protected]> 250 2.1.5 <[email protected]>... Recipient ok DEBUG SMTP: Verified Addresses DEBUG SMTP: Jason Thrasher <[email protected]> DATA 354 Enter mail, end with "." on a line by itself Hello World: message body here . 250 2.0.0 n5I0pkSc090137 Message accepted for delivery QUIT 221 2.0.0 mail.authsmtp.com closing connection Here's the actual mail.jsp that I'm testing war/non-war with. <%@page import="java.util.*"%> <%@page import="javax.mail.internet.*"%> <%@page import="javax.mail.*"%> <% InternetAddress from = new InternetAddress("[email protected]", "Webmaster"); InternetAddress to = new InternetAddress("[email protected]", "Jason Thrasher"); String subject = "non-Spring: Hello World"; String content = "Hello World: message body here"; final Properties props = new Properties(); props.setProperty("mail.transport.protocol", "smtp"); props.setProperty("mail.host", "mail.authsmtp.com"); props.setProperty("mail.port", "465"); props.setProperty("mail.username", "myusername"); props.setProperty("mail.password", "secret"); props.setProperty("mail.debug", "true"); props.setProperty("mail.smtp.auth", "true"); props.setProperty("mail.smtp.socketFactory.class", "javax.net.ssl.SSLSocketFactory"); props.setProperty("mail.smtp.socketFactory.fallback", "false"); Session mailSession = Session.getDefaultInstance(props); Message message = new MimeMessage(mailSession); message.setFrom(from); message.setRecipient(Message.RecipientType.TO, to); message.setSubject(subject); message.setContent(content, "text/plain;charset=UTF-8"); Transport trans = mailSession.getTransport(); trans.connect(props.getProperty("mail.host"), Integer .parseInt(props.getProperty("mail.port")), props .getProperty("mail.username"), props .getProperty("mail.password")); trans.sendMessage(message, message .getRecipients(Message.RecipientType.TO)); trans.close(); %> email was sent SOLUTION: Yes, the problem was transitive dependencies of Apache CXF 2. I had to exclude geronimo-javamail_1.4_spec from the build, and just rely on javax's mail-1.4.jar. <dependency> <groupId>org.apache.cxf</groupId> <artifactId>cxf-rt-frontend-jaxws</artifactId> <version>2.2.6</version> <exclusions> <exclusion> <groupId>org.apache.geronimo.specs</groupId> <artifactId>geronimo-javamail_1.4_spec</artifactId> </exclusion> </exclusions> </dependency> Thanks for all of the answers.

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