Getting "MessagingException: Could not convert socket to TLS" when sending mail via SMTP

java smtp jakarta-mail starttls
17,186

Looks like something is going wrong in the JDK's SSL support. Perhaps something about the certificate from the server is confusing it. You're using a pretty old version of the JDK. I would try upgrading to a current version to see if that resolves the problem. You can also try enabling some of the low level SSL debugging output in the JDK, as described in the links in the JavaMail SSLNOTES.txt.

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xpages-noob
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xpages-noob

Updated on June 04, 2022

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  • xpages-noob
    xpages-noob almost 2 years

    When using JavaMail to send a message via SMTP (+STARTTLS) the following exception is raised:

    javax.mail.MessagingException: Could not convert socket to TLS;
nested exception is:
javax.net.ssl.SSLException: java.lang.ArrayIndexOutOfBoundsException

    Multiple posts here (on stackoverflow) and elsewhere suggest that some properties for the mail transport session, namely

    props.put("mail.smtp.starttls.enable","true");
props.put("mail.smtp.ssl.trust","*");

    play a role in solving this issue, but I have tried all combinations of those parameters (present / absent), and none of them solves the problem.

    Does anybody have an idea how to fix this?

    Additional Information / Details:

    Java version: 1.6.0

    JavaMail version: 1.5.2

    Properties for mail transport session:

    props.put("mail.transport.protocol","smtp");
props.put("mail.smtp.host","XXX");
props.put("mail.smtp.port","587");
props.put("mail.smtp.auth","true");
props.put("mail.smtp.starttls.enable","true");
props.put("mail.smtp.ssl.trust","*");
props.put("mail.smtp.user","XXX");
props.put("mail.smtp.password","XXX");
props.put("mail.smtp.connectiontimeout","60000");
props.put("mail.smtp.timeout","600000");
props.put("mail.smtp.writetimeout","60000");

    Debug output from JavaMail (before Exception is raised):

    DEBUG: JavaMail version 1.5.2
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.
MTPTransport,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 Mi
rosystems, 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,
mtps,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: need username and password for authentication
DEBUG SMTP: useEhlo true, useAuth true
DEBUG SMTP: trying to connect to host "XXX", port 587, isSSL false
220 bsmtp.bon.at ESMTP (1)
DEBUG SMTP: connected to host "XXX", port: 587
EHLO ZZZ
250-bsmtp.bon.at
250-PIPELINING
250-SIZE 104857600
250-ETRN
250-STARTTLS
250-ENHANCEDSTATUSCODES
250 8BITMIME
DEBUG SMTP: Found extension "PIPELINING", arg ""
DEBUG SMTP: Found extension "SIZE", arg "104857600"
DEBUG SMTP: Found extension "ETRN", arg ""
DEBUG SMTP: Found extension "STARTTLS", arg ""
DEBUG SMTP: Found extension "ENHANCEDSTATUSCODES", arg ""
DEBUG SMTP: Found extension "8BITMIME", arg ""
STARTTLS
220 2.0.0 Ready to start TLS

    Full stacktrace for the exception:

    javax.mail.MessagingException: Could not convert socket to TLS;
  nested exception is:
    javax.net.ssl.SSLException: java.lang.ArrayIndexOutOfBoundsException
    at com.sun.mail.smtp.SMTPTransport.startTLS(SMTPTransport.java:1999)
    at com.sun.mail.smtp.SMTPTransport.protocolConnect(SMTPTransport.java:709)
    at javax.mail.Service.connect(Service.java:386)
    at javax.mail.Service.connect(Service.java:245)
    at javax.mail.Service.connect(Service.java:194)
    at com.safebook.MailMessage.send(MailMessage.java:144)
    at com.safebook.MailMessage.send(MailMessage.java:80)
    at sun.reflect.NativeMethodAccessorImpl.invoke0(Native Method)
    at sun.reflect.NativeMethodAccessorImpl.invoke(NativeMethodAccessorImpl.java:60)
    at sun.reflect.DelegatingMethodAccessorImpl.invoke(DelegatingMethodAccessorImpl.java:37)
    at java.lang.reflect.Method.invoke(Method.java:611)
    at com.ibm.jscript.types.JavaAccessObject.call(JavaAccessObject.java:321)
    at com.ibm.jscript.types.FBSObject.call(FBSObject.java:161)
    at com.ibm.jscript.ASTTree.ASTCall.interpret(ASTCall.java:197)
    at com.ibm.jscript.ASTTree.ASTAssign.interpret(ASTAssign.java:91)
    at com.ibm.jscript.ASTTree.ASTBlock.interpret(ASTBlock.java:100)
    at com.ibm.jscript.ASTTree.ASTTry.interpret(ASTTry.java:109)
    at com.ibm.jscript.std.FunctionObject._executeFunction(FunctionObject.java:261)
    at com.ibm.jscript.std.FunctionObject.executeFunction(FunctionObject.java:185)
    at com.ibm.jscript.std.FunctionObject.call(FunctionObject.java:171)
    at com.ibm.jscript.types.FBSObject.call(FBSObject.java:161)
    at com.ibm.jscript.ASTTree.ASTCall.interpret(ASTCall.java:197)
    at com.ibm.jscript.ASTTree.ASTIf.interpret(ASTIf.java:85)
    at com.ibm.jscript.ASTTree.ASTProgram.interpret(ASTProgram.java:119)
    at com.ibm.jscript.types.FBSGlobalObject$GlobalMethod.call(FBSGlobalObject.java:280)
    at com.ibm.jscript.types.FBSObject.call(FBSObject.java:161)
    at com.ibm.jscript.types.FBSGlobalObject$GlobalMethod.call(FBSGlobalObject.java:219)
    at com.ibm.jscript.ASTTree.ASTCall.interpret(ASTCall.java:197)
    at com.ibm.jscript.ASTTree.ASTBlock.interpret(ASTBlock.java:100)
    at com.ibm.jscript.ASTTree.ASTTry.interpret(ASTTry.java:109)
    at com.ibm.jscript.ASTTree.ASTProgram.interpret(ASTProgram.java:119)
    at com.ibm.jscript.ASTTree.ASTProgram.interpretEx(ASTProgram.java:139)
    at com.ibm.jscript.JSExpression._interpretExpression(JSExpression.java:435)
    at com.ibm.jscript.JSExpression.access$1(JSExpression.java:424)
    at com.ibm.jscript.JSExpression$2.run(JSExpression.java:414)
    at java.security.AccessController.doPrivileged(AccessController.java:448)
    at com.ibm.jscript.JSExpression.interpretExpression(JSExpression.java:410)
    at com.ibm.jscript.JSExpression.evaluateValue(JSExpression.java:251)
    at com.ibm.jscript.JSExpression.evaluateValue(JSExpression.java:234)
    at com.ibm.xsp.javascript.JavaScriptInterpreter.interpret(JavaScriptInterpreter.java:222)
    at com.ibm.xsp.binding.javascript.JavaScriptMethodBinding.invoke(JavaScriptMethodBinding.java:111)
    at com.ibm.xsp.component.UIViewRootEx.initBeforeContents(UIViewRootEx.java:1621)
    at com.ibm.xsp.page.compiled.AbstractCompiledPage.initComponent(AbstractCompiledPage.java:333)
    at com.ibm.xsp.page.compiled.AbstractCompiledPage.createTree(AbstractCompiledPage.java:256)
    at com.ibm.xsp.page.compiled.AbstractCompiledPage.createViewRoot(AbstractCompiledPage.java:167)
    at com.ibm.xsp.application.ViewHandlerExImpl._createViewRoot(ViewHandlerExImpl.java:521)
    at com.ibm.xsp.application.ViewHandlerExImpl.createViewRoot(ViewHandlerExImpl.java:567)
    at com.ibm.xsp.application.ViewHandlerExImpl.doCreateView(ViewHandlerExImpl.java:142)
    at com.ibm.xsp.application.ViewHandlerEx.createView(ViewHandlerEx.java:90)
    at com.ibm.xsp.webapp.FacesServlet.serviceView(FacesServlet.java:251)
    at com.ibm.xsp.webapp.FacesServletEx.serviceView(FacesServletEx.java:157)
    at com.ibm.xsp.webapp.FacesServlet.service(FacesServlet.java:160)
    at com.ibm.xsp.webapp.FacesServletEx.service(FacesServletEx.java:138)
    at com.ibm.xsp.webapp.DesignerFacesServlet.service(DesignerFacesServlet.java:103)
    at com.ibm.designer.runtime.domino.adapter.ComponentModule.invokeServlet(ComponentModule.java:576)
    at com.ibm.domino.xsp.module.nsf.NSFComponentModule.invokeServlet(NSFComponentModule.java:1335)
    at com.ibm.designer.runtime.domino.adapter.ComponentModule$AdapterInvoker.invokeServlet(ComponentModule.java:853)
    at com.ibm.designer.runtime.domino.adapter.ComponentModule$ServletInvoker.doService(ComponentModule.java:796)
    at com.ibm.designer.runtime.domino.adapter.ComponentModule.doService(ComponentModule.java:565)
    at com.ibm.domino.xsp.module.nsf.NSFComponentModule.doService(NSFComponentModule.java:1319)
    at com.ibm.domino.xsp.module.nsf.NSFService.doServiceInternal(NSFService.java:662)
    at com.ibm.domino.xsp.module.nsf.NSFService.doService(NSFService.java:482)
    at com.ibm.designer.runtime.domino.adapter.LCDEnvironment.doService(LCDEnvironment.java:357)
    at com.ibm.designer.runtime.domino.adapter.LCDEnvironment.service(LCDEnvironment.java:313)
    at com.ibm.domino.xsp.bridge.http.engine.XspCmdManager.service(XspCmdManager.java:272)
Caused by: 
javax.net.ssl.SSLException: java.lang.ArrayIndexOutOfBoundsException
    at com.ibm.jsse2.o.a(o.java:26)
    at com.ibm.jsse2.SSLSocketImpl.a(SSLSocketImpl.java:340)
    at com.ibm.jsse2.SSLSocketImpl.a(SSLSocketImpl.java:225)
    at com.ibm.jsse2.SSLSocketImpl.a(SSLSocketImpl.java:367)
    at com.ibm.jsse2.SSLSocketImpl.a(SSLSocketImpl.java:32)
    at com.ibm.jsse2.SSLSocketImpl.startHandshake(SSLSocketImpl.java:95)
    at com.sun.mail.util.SocketFetcher.configureSSLSocket(SocketFetcher.java:543)
    at com.sun.mail.util.SocketFetcher.startTLS(SocketFetcher.java:480)
    at com.sun.mail.smtp.SMTPTransport.startTLS(SMTPTransport.java:1994)
    ... 64 more
Caused by: 
java.lang.ArrayIndexOutOfBoundsException
    at com.ibm.crypto.provider.yc.a(Unknown Source)
    at com.ibm.crypto.provider.yc.a(Unknown Source)
    at com.ibm.crypto.provider.yc.a(Unknown Source)
    at com.ibm.crypto.provider.TlsMasterSecretGenerator.engineGenerateKey(Unknown Source)
    at javax.crypto.KeyGenerator.generateKey(Unknown Source)
    at com.ibm.jsse2.kb.b(kb.java:114)
    at com.ibm.jsse2.kb.a(kb.java:138)
    at com.ibm.jsse2.lb.a(lb.java:113)
    at com.ibm.jsse2.lb.a(lb.java:120)
    at com.ibm.jsse2.kb.t(kb.java:227)
    at com.ibm.jsse2.kb.a(kb.java:425)
    at com.ibm.jsse2.SSLSocketImpl.a(SSLSocketImpl.java:785)
    at com.ibm.jsse2.SSLSocketImpl.h(SSLSocketImpl.java:675)
    at com.ibm.jsse2.SSLSocketImpl.a(SSLSocketImpl.java:669)
    ... 68 more

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