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Error while configuring mail server

Amit Rotti
Amit Rotti February 18, 2013

Hi,

We are not able to configure mail server and we are getting error as

"Caused by: javax.mail.MessagingException: Could not connect to SMTP host: smtp.gmail.com, port: 587" and also we have tried to configure our smtp server and getting error as "Caused by: java.net.SocketException: Permission denied: connect"

Kindly help us to resolve this error. NOTE: We are trying this from both Windows and Linux OS.

Here are the logs for both scenarios,

***** When tried to configure our gmail smtp server as instructed *****

[catalina.jar:7.0.32]

at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:210) [catalina.jar:7.0.32]

at org.apache.catalina.core.StandardWrapperValve.invoke(StandardWrapperValve.java:222) [catalina.jar:7.0.32]

at org.apache.catalina.core.StandardContextValve.invoke(StandardContextValve.java:123) [catalina.jar:7.0.32]

at org.apache.catalina.core.StandardHostValve.invoke(StandardHostValve.java:168) [catalina.jar:7.0.32]

at org.apache.catalina.valves.ErrorReportValve.invoke(ErrorReportValve.java:99) [catalina.jar:7.0.32]

at org.apache.catalina.core.StandardEngineValve.invoke(StandardEngineValve.java:118) [catalina.jar:7.0.32]

at org.apache.catalina.connector.CoyoteAdapter.service(CoyoteAdapter.java:407) [catalina.jar:7.0.32]

at org.apache.coyote.http11.AbstractHttp11Processor.process(AbstractHttp11Processor.java:1002) [tomcat-coyote.jar:7.0.32]

at org.apache.coyote.AbstractProtocol$AbstractConnectionHandler.process(AbstractProtocol.java:585) [tomcat-coyote.jar:7.0.32]

at org.apache.tomcat.util.net.JIoEndpoint$SocketProcessor.run(JIoEndpoint.java:310) [tomcat-coyote.jar:7.0.32]

at java.util.concurrent.ThreadPoolExecutor.runWorker(ThreadPoolExecutor.java:1110) [na:1.7.0_10]

at java.util.concurrent.ThreadPoolExecutor$Worker.run(ThreadPoolExecutor.java:603) [na:1.7.0_10]

at java.lang.Thread.run(Thread.java:722) [na:1.7.0_10]

Caused by: javax.mail.MessagingException: Could not connect to SMTP host: smtp.gmail.com, port: 587

at com.sun.mail.smtp.SMTPTransport.openServer(SMTPTransport.java:1972) ~[mail-1.4.5.jar:1.4.5]

at com.sun.mail.smtp.SMTPTransport.protocolConnect(SMTPTransport.java:642) ~[mail-1.4.5.jar:1.4.5]

at javax.mail.Service.connect(Service.java:295) ~[mail-1.4.5.jar:1.4.5]

at org.springframework.mail.javamail.JavaMailSenderImpl.doSend(JavaMailSenderImpl.java:389) ~[spring-context-support-3.1.2.RELEASE.jar:3.1.2.RELEASE]

... 206 common frames omitted

Caused by: java.net.ConnectException: Connection timed out: connect

at java.net.DualStackPlainSocketImpl.waitForConnect(Native Method) ~[na:1.7.0_10]

at java.net.DualStackPlainSocketImpl.socketConnect(DualStackPlainSocketImpl.java:75) ~[na:1.7.0_10]

at java.net.AbstractPlainSocketImpl.doConnect(AbstractPlainSocketImpl.java:339) ~[na:1.7.0_10]

at java.net.AbstractPlainSocketImpl.connectToAddress(AbstractPlainSocketImpl.java:200) ~[na:1.7.0_10]

at java.net.AbstractPlainSocketImpl.connect(AbstractPlainSocketImpl.java:182) ~[na:1.7.0_10]

at java.net.PlainSocketImpl.connect(PlainSocketImpl.java:157) ~[na:1.7.0_10]

at java.net.SocksSocketImpl.connect(SocksSocketImpl.java:391) ~[na:1.7.0_10]

at java.net.Socket.connect(Socket.java:579) ~[na:1.7.0_10]

at com.sun.mail.util.SocketFetcher.createSocket(SocketFetcher.java:317) ~[mail-1.4.5.jar:1.4.5]

at com.sun.mail.util.SocketFetcher.getSocket(SocketFetcher.java:233) ~[mail-1.4.5.jar:1.4.5]

at com.sun.mail.smtp.SMTPTransport.openServer(SMTPTransport.java:1938) ~[mail-1.4.5.jar:1.4.5]

... 209 common frames omitted

#####################################################################################################################

***** When tried to configure our smtp servers *****

[catalina.jar:7.0.32]

at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:210) [catalina.jar:7.0.32]

at org.apache.catalina.core.StandardWrapperValve.invoke(StandardWrapperValve.java:222) [catalina.jar:7.0.32]

at org.apache.catalina.core.StandardContextValve.invoke(StandardContextValve.java:123) [catalina.jar:7.0.32]

at org.apache.catalina.core.StandardHostValve.invoke(StandardHostValve.java:168) [catalina.jar:7.0.32]

at org.apache.catalina.valves.ErrorReportValve.invoke(ErrorReportValve.java:99) [catalina.jar:7.0.32]

at org.apache.catalina.core.StandardEngineValve.invoke(StandardEngineValve.java:118) [catalina.jar:7.0.32]

at org.apache.catalina.connector.CoyoteAdapter.service(CoyoteAdapter.java:407) [catalina.jar:7.0.32]

at org.apache.coyote.http11.AbstractHttp11Processor.process(AbstractHttp11Processor.java:1002) [tomcat-coyote.jar:7.0.32]

at org.apache.coyote.AbstractProtocol$AbstractConnectionHandler.process(AbstractProtocol.java:585) [tomcat-coyote.jar:7.0.32]

at org.apache.tomcat.util.net.JIoEndpoint$SocketProcessor.run(JIoEndpoint.java:312) [tomcat-coyote.jar:7.0.32]

at java.util.concurrent.ThreadPoolExecutor.runWorker(ThreadPoolExecutor.java:1110) [na:1.7.0_10]

at java.util.concurrent.ThreadPoolExecutor$Worker.run(ThreadPoolExecutor.java:603) [na:1.7.0_10]

at java.lang.Thread.run(Thread.java:722) [na:1.7.0_10]

Caused by: javax.mail.MessagingException: Could not connect to SMTP host: remotesmtp.hostName.com, port: 25

at com.sun.mail.smtp.SMTPTransport.openServer(SMTPTransport.java:1972) ~[mail-1.4.5.jar:1.4.5]

at com.sun.mail.smtp.SMTPTransport.protocolConnect(SMTPTransport.java:642) ~[mail-1.4.5.jar:1.4.5]

at javax.mail.Service.connect(Service.java:295) ~[mail-1.4.5.jar:1.4.5]

at org.springframework.mail.javamail.JavaMailSenderImpl.doSend(JavaMailSenderImpl.java:389) ~[spring-context-support-3.1.2.RELEASE.jar:3.1.2.RELEASE]

... 177 common frames omitted

Caused by: java.net.SocketException: Permission denied: connect

at java.net.DualStackPlainSocketImpl.waitForConnect(Native Method) ~[na:1.7.0_10]

at java.net.DualStackPlainSocketImpl.socketConnect(DualStackPlainSocketImpl.java:75) ~[na:1.7.0_10]

at java.net.AbstractPlainSocketImpl.doConnect(AbstractPlainSocketImpl.java:339) ~[na:1.7.0_10]

at java.net.AbstractPlainSocketImpl.connectToAddress(AbstractPlainSocketImpl.java:200) ~[na:1.7.0_10]

at java.net.AbstractPlainSocketImpl.connect(AbstractPlainSocketImpl.java:182) ~[na:1.7.0_10]

at java.net.PlainSocketImpl.connect(PlainSocketImpl.java:157) ~[na:1.7.0_10]

at java.net.SocksSocketImpl.connect(SocksSocketImpl.java:391) ~[na:1.7.0_10]

at java.net.Socket.connect(Socket.java:579) ~[na:1.7.0_10]

at com.sun.mail.util.SocketFetcher.createSocket(SocketFetcher.java:317) ~[mail-1.4.5.jar:1.4.5]

at com.sun.mail.util.SocketFetcher.getSocket(SocketFetcher.java:233) ~[mail-1.4.5.jar:1.4.5]

at com.sun.mail.smtp.SMTPTransport.openServer(SMTPTransport.java:1938) ~[mail-1.4.5.jar:1.4.5]

... 180 common frames omitted

2013-02-19 19:52:48,054 INFO [AtlassianEvent::pool-3-thread-3] hcmd48 1192x895x1 1cr4ov8 10.232.70.66 "POST /admin/mail-server HTTP/1.1" stash.mail-log MailService reconfigured

2013-02-19 19:53:14,587 ERROR [http-bio-7990-exec-3] hcmd48 1192x900x1 1cr4ov8 10.232.70.66 "POST /admin/mail-server HTTP/1.1" stash.mail-log Message not sent: Mail sending failed; recipient: a22732@companyName.com; subject: MOTOROLA - Test email for your SMTP configuration

org.springframework.mail.MailSendException: Mail server connection failed; nested exception is javax.mail.MessagingException: Could not connect to SMTP host: smtp.gmail.com, port: 857;

nested exception is:

java.net.ConnectException: Connection timed out: connect. Failed messages: javax.mail.MessagingException: Could not connect to SMTP host: smtp.gmail.com, port: 857;

nested exception is:

java.net.ConnectException: Connection timed out: connect

at org.springframework.mail.javamail.JavaMailSenderImpl.doSend(JavaMailSenderImpl.java:400) ~[spring-context-support-3.1.2.RELEASE.jar:3.1.2.RELEASE]

at org.springframework.mail.javamail.JavaMailSenderImpl.send(JavaMailSenderImpl.java:340) ~[spring-context-support-3.1.2.RELEASE.jar:3.1.2.RELEASE]

at org.springframework.mail.javamail.JavaMailSenderImpl.send(JavaMailSenderImpl.java:355) ~[spring-context-support-3.1.2.RELEASE.jar:3.1.2.RELEASE]

at org.springframework.mail.javamail.JavaMailSenderImpl.send(JavaMailSenderImpl.java:344) ~[spring-context-support-3.1.2.RELEASE.jar:3.1.2.RELEASE]

at com.atlassian.stash.internal.mail.MailServiceImpl.sendMessageSynchronously(MailServiceImpl.java:205) [stash-service-impl-2.0.2.jar:na]

at com.atlassian.stash.internal.mail.MailServiceImpl.sendTest(MailServiceImpl.java:198) [stash-service-impl-2.0.2.jar:na]

at sun.reflect.GeneratedMethodAccessor450.invoke(Unknown Source) ~[na:na]

at sun.reflect.DelegatingMethodAccessorImpl.invoke(DelegatingMethodAccessorImpl.java:43) ~[na:1.7.0_10]

at java.lang.reflect.Method.invoke(Method.java:601) ~[na:1.7.0_10]

at org.springframework.aop.support.AopUtils.invokeJoinpointUsingReflection(AopUtils.java:319) [spring-aop-3.1.2.RELEASE.jar:3.1.2.RELEASE]

at org.springframework.aop.framework.ReflectiveMethodInvocation.invokeJoinpoint(ReflectiveMethodInvocation.java:183) [spring-aop-3.1.2.RELEASE.jar:3.1.2.RELEASE]

at org.springframework.aop.framework.ReflectiveMethodInvocation.proceed(ReflectiveMethodInvocation.java:150) [spring-aop-3.1.2.RELEASE.jar:3.1.2.RELEASE]

at org.springframework.security.access.intercept.aopalliance.MethodSecurityInterceptor.invoke(MethodSecurityInterceptor.java:61) [spring-security-core-3.1.0.RELEASE.jar:3.1.0.RELEASE]

at org.springframework.aop.framework.ReflectiveMethodInvocation.proceed(ReflectiveMethodInvocation.java:172) [spring-aop-3.1.2.RELEASE.jar:3.1.2.RELEASE]

at org.springframework.aop.framework.JdkDynamicAopProxy.invoke(JdkDynamicAopProxy.java:202) [spring-aop-3.1.2.RELEASE.jar:3.1.2.RELEASE]

at $Proxy190.sendTest(Unknown Source) [na:na]

at com.atlassian.stash.internal.web.admin.MailServerConfigurationController.testSettings(MailServerConfigurationController.java:77) [MailServerConfigurationController.class:na]

at sun.reflect.GeneratedMethodAccessor449.invoke(Unknown Source) ~[na:na]

at sun.reflect.DelegatingMethodAccessorImpl.invoke(DelegatingMethodAccessorImpl.java:43) ~[na:1.7.0_10]

at java.lang.reflect.Method.invoke(Method.java:601) ~[na:1.7.0_10]

at org.springframework.web.method.support.InvocableHandlerMethod.invoke(InvocableHandlerMethod.java:213) [spring-web-3.1.2.RELEASE.jar:3.1.2.RELEASE]

at org.springframework.web.method.support.InvocableHandlerMethod.invokeForRequest(InvocableHandlerMethod.java:126) [spring-web-3.1.2.RELEASE.jar:3.1.2.RELEASE]

at org.springframework.web.servlet.mvc.method.annotation.ServletInvocableHandlerMethod.invokeAndHandle(ServletInvocableHandlerMethod.java:96) [spring-webmvc-3.1.2.RELEASE.jar:3.1.2.RELEASE]

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cofarrell
cofarrell
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February 19, 2013

Hi Amit,

Looks like there might be two different problems here. The first error "Permission denied: connect" is sometimes caused by a bug on JDK7, which can be fixed by adding the following to setenv.sh or setenv.bat on Windows.

-Djava.net.preferIPv4Stack=true

Another exception is talking about port 857, which is incorrect. It should be port 465 (with SSL) or port 587 (with TLS),

http://support.google.com/mail/bin/answer.py?hl=en&answer=78775

I hope this helps.

Charles

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Ivan Tse
Ivan Tse
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Atlassian Team members are employees working across the company in a wide variety of roles.
February 19, 2013

You should also check the protocol you're using. I believe that google apps only allow secure prococols (SMTP/S, IMAP/S, POP/s). Make sure those protocols are selected.

In JIRA there is an option to just ust the pre-definied Google Apps/Gmail option that should populate the right options.

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Amit Rotti
Amit Rotti April 3, 2013

Hi Charles and Ivan,

Thanks for reply, it worked for me. :)

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