keycloak email verifiation not working

Question

I am playing with keycloak and created a realm. I have set up the login to enable forget username and verify email. In the email tab I entered

host - smtp.gmail.com
port - 477
username - ***@gmail.com
SSL - enabled
Authentication - enabled with username and password 

Now when I go onto the login page and click forgot password or register a user then keycloak is not able to send email.

I get the error

ERROR [org.keycloak.services] (default task-1) KC-SERVICES0026: Failed to send password reset email: org.keycloak.email.EmailException: Failed to template email
    at org.keycloak.email.freemarker.FreeMarkerEmailTemplateProvider.send(FreeMarkerEmailTemplateProvider.java:185)
    at org.keycloak.email.freemarker.FreeMarkerEmailTemplateProvider.send(FreeMarkerEmailTemplateProvider.java:156)
    at org.keycloak.email.freemarker.FreeMarkerEmailTemplateProvider.sendPasswordReset(FreeMarkerEmailTemplateProvider.java:107)
    at org.keycloak.authentication.authenticators.resetcred.ResetCredentialEmail.authenticate(ResetCredentialEmail.java:96)
    at org.keycloak.authentication.DefaultAuthenticationFlow.processFlow(DefaultAuthenticationFlow.java:184)
    at org.keycloak.authentication.AuthenticationProcessor.authenticateOnly(AuthenticationProcessor.java:792)
    at org.keycloak.authentication.AuthenticationProcessor.authenticate(AuthenticationProcessor.java:667)
    at org.keycloak.services.resources.LoginActionsService.processFlow(LoginActionsService.java:358)
    at org.keycloak.services.resources.LoginActionsService.processResetCredentials(LoginActionsService.java:472)
    at org.keycloak.services.resources.LoginActionsService.resetCredentials(LoginActionsService.java:447)
    at org.keycloak.services.resources.LoginActionsService.resetCredentialsGET(LoginActionsService.java:428)
    at sun.reflect.NativeMethodAccessorImpl.invoke0(Native Method)
    at sun.reflect.NativeMethodAccessorImpl.invoke(NativeMethodAccessorImpl.java:62)
    at sun.reflect.DelegatingMethodAccessorImpl.invoke(DelegatingMethodAccessorImpl.java:43)
    at java.lang.reflect.Method.invoke(Method.java:498)
    at org.jboss.resteasy.core.MethodInjectorImpl.invoke(MethodInjectorImpl.java:139)
    at org.jboss.resteasy.core.ResourceMethodInvoker.invokeOnTarget(ResourceMethodInvoker.java:295)
    at org.jboss.resteasy.core.ResourceMethodInvoker.invoke(ResourceMethodInvoker.java:249)
    at org.jboss.resteasy.core.ResourceLocatorInvoker.invokeOnTargetObject(ResourceLocatorInvoker.java:138)
    at org.jboss.resteasy.core.ResourceLocatorInvoker.invoke(ResourceLocatorInvoker.java:101)
    at org.jboss.resteasy.core.SynchronousDispatcher.invoke(SynchronousDispatcher.java:395)
    at org.jboss.resteasy.core.SynchronousDispatcher.invoke(SynchronousDispatcher.java:202)
    at org.jboss.resteasy.plugins.server.servlet.ServletContainerDispatcher.service(ServletContainerDispatcher.java:221)
    at org.jboss.resteasy.plugins.server.servlet.HttpServletDispatcher.service(HttpServletDispatcher.java:56)
    at org.jboss.resteasy.plugins.server.servlet.HttpServletDispatcher.service(HttpServletDispatcher.java:51)
    at javax.servlet.http.HttpServlet.service(HttpServlet.java:790)
    at io.undertow.servlet.handlers.ServletHandler.handleRequest(ServletHandler.java:85)
    at io.undertow.servlet.handlers.FilterHandler$FilterChainImpl.doFilter(FilterHandler.java:129)
    at org.keycloak.services.filters.KeycloakSessionServletFilter.doFilter(KeycloakSessionServletFilter.java:90)
    at io.undertow.servlet.core.ManagedFilter.doFilter(ManagedFilter.java:60)
    at io.undertow.servlet.handlers.FilterHandler$FilterChainImpl.doFilter(FilterHandler.java:131)
    at io.undertow.servlet.handlers.FilterHandler.handleRequest(FilterHandler.java:84)
    at io.undertow.servlet.handlers.security.ServletSecurityRoleHandler.handleRequest(ServletSecurityRoleHandler.java:62)
    at io.undertow.servlet.handlers.ServletDispatchingHandler.handleRequest(ServletDispatchingHandler.java:36)
    at org.wildfly.extension.undertow.security.SecurityContextAssociationHandler.handleRequest(SecurityContextAssociationHandler.java:78)
    at io.undertow.server.handlers.PredicateHandler.handleRequest(PredicateHandler.java:43)
    at io.undertow.servlet.handlers.security.SSLInformationAssociationHandler.handleRequest(SSLInformationAssociationHandler.java:131)
    at io.undertow.servlet.handlers.security.ServletAuthenticationCallHandler.handleRequest(ServletAuthenticationCallHandler.java:57)
    at io.undertow.server.handlers.PredicateHandler.handleRequest(PredicateHandler.java:43)
    at io.undertow.security.handlers.AbstractConfidentialityHandler.handleRequest(AbstractConfidentialityHandler.java:46)
    at io.undertow.servlet.handlers.security.ServletConfidentialityConstraintHandler.handleRequest(ServletConfidentialityConstraintHandler.java:64)
    at io.undertow.security.handlers.AuthenticationMechanismsHandler.handleRequest(AuthenticationMechanismsHandler.java:60)
    at io.undertow.servlet.handlers.security.CachedAuthenticatedSessionHandler.handleRequest(CachedAuthenticatedSessionHandler.java:77)
    at io.undertow.security.handlers.NotificationReceiverHandler.handleRequest(NotificationReceiverHandler.java:50)
    at io.undertow.security.handlers.AbstractSecurityContextAssociationHandler.handleRequest(AbstractSecurityContextAssociationHandler.java:43)
    at io.undertow.server.handlers.PredicateHandler.handleRequest(PredicateHandler.java:43)
    at org.wildfly.extension.undertow.security.jacc.JACCContextIdHandler.handleRequest(JACCContextIdHandler.java:61)
    at io.undertow.server.handlers.PredicateHandler.handleRequest(PredicateHandler.java:43)
    at io.undertow.server.handlers.PredicateHandler.handleRequest(PredicateHandler.java:43)
    at io.undertow.servlet.handlers.ServletInitialHandler.handleFirstRequest(ServletInitialHandler.java:284)
    at io.undertow.servlet.handlers.ServletInitialHandler.dispatchRequest(ServletInitialHandler.java:263)
    at io.undertow.servlet.handlers.ServletInitialHandler.access$000(ServletInitialHandler.java:81)
    at io.undertow.servlet.handlers.ServletInitialHandler$1.handleRequest(ServletInitialHandler.java:174)
    at io.undertow.server.Connectors.executeRootHandler(Connectors.java:202)
    at io.undertow.server.HttpServerExchange$1.run(HttpServerExchange.java:793)
    at java.util.concurrent.ThreadPoolExecutor.runWorker(ThreadPoolExecutor.java:1142)
    at java.util.concurrent.ThreadPoolExecutor$Worker.run(ThreadPoolExecutor.java:617)
    at java.lang.Thread.run(Thread.java:745)
Caused by: org.keycloak.email.EmailException: com.sun.mail.util.MailConnectException: Couldn't connect to host, port: smtp.gmail.com, 466; timeout 10000;
  nested exception is:
    java.net.SocketTimeoutException: connect timed out
    at org.keycloak.email.DefaultEmailSenderProvider.send(DefaultEmailSenderProvider.java:128)
    at org.keycloak.email.freemarker.FreeMarkerEmailTemplateProvider.send(FreeMarkerEmailTemplateProvider.java:191)
    at org.keycloak.email.freemarker.FreeMarkerEmailTemplateProvider.send(FreeMarkerEmailTemplateProvider.java:183)
    ... 57 more
Caused by: com.sun.mail.util.MailConnectException: Couldn't connect to host, port: smtp.gmail.com, 466; timeout 10000;
  nested exception is:
    java.net.SocketTimeoutException: connect timed out
    at com.sun.mail.smtp.SMTPTransport.openServer(SMTPTransport.java:2100)
    at com.sun.mail.smtp.SMTPTransport.protocolConnect(SMTPTransport.java:699)
    at javax.mail.Service.connect(Service.java:366)
    at javax.mail.Service.connect(Service.java:246)
    at javax.mail.Service.connect(Service.java:267)
    at org.keycloak.email.DefaultEmailSenderProvider.send(DefaultEmailSenderProvider.java:121)
    ... 59 more
Caused by: java.net.SocketTimeoutException: connect timed out
    at java.net.PlainSocketImpl.socketConnect(Native Method)
    at java.net.AbstractPlainSocketImpl.doConnect(AbstractPlainSocketImpl.java:350)
    at java.net.AbstractPlainSocketImpl.connectToAddress(AbstractPlainSocketImpl.java:206)
    at java.net.AbstractPlainSocketImpl.connect(AbstractPlainSocketImpl.java:188)
    at java.net.SocksSocketImpl.connect(SocksSocketImpl.java:392)
    at java.net.Socket.connect(Socket.java:589)
    at com.sun.mail.util.SocketFetcher.createSocket(SocketFetcher.java:329)
    at com.sun.mail.util.SocketFetcher.getSocket(SocketFetcher.java:238)
    at com.sun.mail.smtp.SMTPTransport.openServer(SMTPTransport.java:2066)
    ... 64 more

Answer 1

Use port 465 for a SSL connection to smtp.gmail.com

Attempting to connect to Port 477 (or 466 in your stack trace) will result in a timeout as there is nothing listening there.