Office 365 SMTP Issue

Hi
I have a local community version of Metabase, but I am unable to get it to configure the email service.

I have tried both smtp-mail.outlook.com and smtp.office365.com Host names, with port 587 and with security setting as STARTTLS, and tried with all other options, but it just keeps coming back with wrong username or password.

But I have logged in with the credentials fine.

The error log states

[c25a73be-0857-45b9-9e60-9efcdb90a9b3] 2024-06-03T13:56:18+01:00 ERROR metabase.email Error testing SMTP connection,javax.mail.AuthenticationFailedException: ;, nested exception is:, javax.mail.MessagingException: Exception reading response;, nested exception is:, java.net.SocketTimeoutException: Read timed out, at com.sun.mail.smtp.SMTPTransport$Authenticator.authenticate(SMTPTransport.java:942), at com.sun.mail.smtp.SMTPTransport.authenticate(SMTPTransport.java:858), at com.sun.mail.smtp.SMTPTransport.protocolConnect(SMTPTransport.java:762), at javax.mail.Service.connect(Service.java:342), at metabase.email$test_smtp_settings$fn__75838.invoke(email.clj:235), at metabase.email$test_smtp_settings.invokeStatic(email.clj:234), at metabase.email$test_smtp_settings.invoke(email.clj:220), at metabase.email$test_smtp_connection.invokeStatic(email.clj:280), at metabase.email$test_smtp_connection.invoke(email.clj:266), at metabase.api.email$fn__87131.invokeStatic(email.clj:112), at metabase.api.email$fn__87131.invoke(email.clj:92), at compojure.core$wrap_response$fn__44682.invoke(core.clj:160), at compojure.core$wrap_route_middleware$fn__44666.invoke(core.clj:132), at compojure.core$wrap_route_info$fn__44671.invoke(core.clj:139), at compojure.core$wrap_route_matches$fn__44675.invoke(core.clj:151), at clojure.lang.Var.invoke(Var.java:393), at compojure.core$routes$fn__44694$f__44695.invoke(core.clj:198), at compojure.core$routes$fn__44694$f__44695$respond_SINGLEQUOTE___44696.invoke(core.clj:197), at compojure.core$wrap_route_matches$fn__44675.invoke(core.clj:153), at clojure.lang.Var.invoke(Var.java:393), at compojure.core$routes$fn__44694$f__44695.invoke(core.clj:198), at compojure.core$routes$fn__44694.invoke(core.clj:200), at metabase.server.middleware.auth$enforce_authentication$fn__94085.invoke(auth.clj:17), at compojure.core$routes$fn__44694$f__44695.invoke(core.clj:198), at compojure.core$routes$fn__44694.invoke(core.clj:200), at compojure.core$make_context$handler__44722.invoke(core.clj:290), at compojure.core$make_context$fn__44726.invoke(core.clj:300), at compojure.core$routes$fn__44694$f__44695.invoke(core.clj:198), at compojure.core$routes$fn__44694$f__44695$respond_SINGLEQUOTE___44696.invoke(core.clj:197), at compojure.core$make_context$fn__44726.invoke(core.clj:301), at compojure.core$routes$fn__44694$f__44695.invoke(core.clj:198), at compojure.core$routes$fn__44694$f__44695$respond_SINGLEQUOTE___44696.invoke(core.clj:197), at compojure.core$make_context$fn__44726.invoke(core.clj:301), at compojure.core$routes$fn__44694$f__44695.invoke(core.clj:198), at compojure.core$routes$fn__44694$f__44695$respond_SINGLEQUOTE___44696.invoke(core.clj:197), at compojure.core$make_context$fn__44726.invoke(core.clj:301), at compojure.core$routes$fn__44694$f__44695.invoke(core.clj:198), at compojure.core$routes$fn__44694$f__44695$respond_SINGLEQUOTE___44696.invoke(core.clj:197), at compojure.core$make_context$fn__44726.invoke(core.clj:301), at compojure.core$routes$fn__44694$f__44695.invoke(core.clj:198), at compojure.core$routes$fn__44694$f__44695$respond_SINGLEQUOTE___44696.invoke(core.clj:197), at compojure.core$make_context$fn__44726.invoke(core.clj:301), at compojure.core$routes$fn__44694$f__44695.invoke(core.clj:198), at compojure.core$routes$fn__44694$f__44695$respond_SINGLEQUOTE___44696.invoke(core.clj:197), at compojure.core$make_context$fn__44726.invoke(core.clj:301), at compojure.core$routes$fn__44694$f__44695.invoke(core.clj:198), at compojure.core$routes$fn__44694$f__44695$respond_SINGLEQUOTE___44696.invoke(core.clj:197), at compojure.core$make_context$fn__44726.invoke(core.clj:301), at compojure.core$routes$fn__44694$f__44695.invoke(core.clj:198), at compojure.core$routes$fn__44694$f__44695$respond_SINGLEQUOTE___44696.invoke(core.clj:197), at compojure.core$make_context$fn__44726.invoke(core.clj:301), at compojure.core$routes$fn__44694$f__44695.invoke(core.clj:198), at compojure.core$routes$fn__44694$f__44695$respond_SINGLEQUOTE___44696.invoke(core.clj:197), at compojure.core$make_context$fn__44726.invoke(core.clj:301), at compojure.core$routes$fn__44694$f__44695.invoke(core.clj:198), at compojure.core$routes$fn__44694$f__44695$respond_SINGLEQUOTE___44696.invoke(core.clj:197), at compojure.core$make_context$fn__44726.invoke(core.clj:301), at compojure.core$routes$fn__44694$f__44695.invoke(core.clj:198), at compojure.core$routes$fn__44694$f__44695$respond_SINGLEQUOTE___44696.invoke(core.clj:197), at metabase.api.routes$fn__102118$fn__102121.invoke(routes.clj:67), at compojure.core$routes$fn__44694$f__44695.invoke(core.clj:198), at compojure.core$routes$fn__44694.invoke(core.clj:200), at clojure.lang.AFn.applyToHelper(AFn.java:160), at clojure.lang.AFn.applyTo(AFn.java:144), at clojure.core$apply.invokeStatic(core.clj:667), at clojure.core$apply.invoke(core.clj:662), at metabase.server.routes$fn__102283$fn__102284.doInvoke(routes.clj:72), at clojure.lang.RestFn.invoke(RestFn.java:436), at compojure.core$routes$fn__44694$f__44695.invoke(core.clj:198), at compojure.core$routes$fn__44694.invoke(core.clj:200), at compojure.core$make_context$handler__44722.invoke(core.clj:290), at compojure.core$make_context$fn__44726.invoke(core.clj:300), at compojure.core$routes$fn__44694$f__44695.invoke(core.clj:198), at compojure.core$routes$fn__44694$f__44695$respond_SINGLEQUOTE___44696.invoke(core.clj:197), at compojure.core$wrap_route_matches$fn__44675.invoke(core.clj:153), at compojure.core$routes$fn__44694$f__44695.invoke(core.clj:198), at compojure.core$routes$fn__44694$f__44695$respond_SINGLEQUOTE___44696.invoke(core.clj:197), at compojure.core$wrap_route_matches$fn__44675.invoke(core.clj:153), at compojure.core$routes$fn__44694$f__44695.invoke(core.clj:198), at compojure.core$routes$fn__44694$f__44695$respond_SINGLEQUOTE___44696.invoke(core.clj:197), at compojure.core$wrap_route_matches$fn__44675.invoke(core.clj:153), at compojure.core$routes$fn__44694$f__44695.invoke(core.clj:198), at compojure.core$routes$fn__44694$f__44695$respond_SINGLEQUOTE___44696.invoke(core.clj:197), at metabase.server.routes$fn__102268$fn__102270.invoke(routes.clj:49), at compojure.core$routes$fn__44694$f__44695.invoke(core.clj:198), at compojure.core$routes$fn__44694.invoke(core.clj:200), at metabase.server.middleware.exceptions$catch_uncaught_exceptions$fn__98829.invoke(exceptions.clj:108), at metabase.server.middleware.exceptions$catch_api_exceptions$fn__98826.invoke(exceptions.clj:96), at metabase.server.middleware.log$log_api_call$fn__102560$fn__102561$fn__102562.invoke(log.clj:230), at metabase.driver.sql_jdbc.execute.diagnostic$do_with_diagnostic_info.invokeStatic(diagnostic.clj:18), at metabase.driver.sql_jdbc.execute.diagnostic$do_with_diagnostic_info.invoke(diagnostic.clj:12), at metabase.server.middleware.log$log_api_call$fn__102560$fn__102561.invoke(log.clj:222), at toucan2.execute$do_with_call_counts.invokeStatic(execute.clj:112), at toucan2.execute$do_with_call_counts.invoke(execute.clj:103), at metabase.server.middleware.log$log_api_call$fn__102560.invoke(log.clj:221), at metabase.server.middleware.browser_cookie$ensure_browser_id_cookie$fn__104625.invoke(browser_cookie.clj:40), at metabase.server.middleware.security$add_security_headers$fn__98785.invoke(security.clj:182), at metabase.server.middleware.json$wrap_json_body$fn__46039.invoke(json.clj:67), at metabase.server.middleware.offset_paging$handle_paging$fn__84983.invoke(offset_paging.clj:43), at metabase.server.middleware.json$wrap_streamed_json_response$fn__46057.invoke(json.clj:103), at ring.middleware.keyword_params$wrap_keyword_params$fn__104892.invoke(keyword_params.clj:55), at ring.middleware.params$wrap_params$fn__104911.invoke(params.clj:77), at metabase.server.middleware.misc$maybe_set_site_url$fn__67273.invoke(misc.clj:61), at metabase.server.middleware.session$reset_session_timeout$fn__72704.invoke(session.clj:546), at metabase.server.middleware.session$bind_current_user$fn__72670$fn__72671.invoke(session.clj:440), at metabase.server.middleware.session$do_with_current_user.invokeStatic(session.clj:419), at metabase.server.middleware.session$do_with_current_user.invoke(session.clj:403), at metabase.server.middleware.session$bind_current_user$fn__72670.invoke(session.clj:439), at metabase.server.middleware.session$wrap_current_user_info$fn__72653.invoke(session.clj:378), at metabase.server.middleware.session$wrap_session_id$fn__72625.invoke(session.clj:257), at metabase.server.middleware.auth$wrap_static_api_key$fn__94093.invoke(auth.clj:30), at ring.middleware.cookies$wrap_cookies$fn__104812.invoke(cookies.clj:194), at metabase.server.middleware.misc$add_content_type$fn__67255.invoke(misc.clj:29), at metabase.server.middleware.misc$disable_streaming_buffering$fn__67281.invoke(misc.clj:78), at ring.middleware.gzip$wrap_gzip$fn__104854.invoke(gzip.clj:86), at metabase.server.middleware.misc$bind_request$fn__67284.invoke(misc.clj:95), at metabase.server.middleware.ssl$redirect_to_https_middleware$fn__104641.invoke(ssl.clj:51), at metabase.server$async_proxy_handler$fn__67695.invoke(server.clj:78), at metabase.server.proxy$org.eclipse.jetty.server.handler.AbstractHandler$ff19274a.handle(Unknown Source), at org.eclipse.jetty.server.handler.StatisticsHandler.handle(StatisticsHandler.java:173), at org.eclipse.jetty.server.handler.HandlerWrapper.handle(HandlerWrapper.java:122), at org.eclipse.jetty.server.Server.handle(Server.java:563), at org.eclipse.jetty.server.HttpChannel$RequestDispatchable.dispatch(HttpChannel.java:1598), at org.eclipse.jetty.server.HttpChannel.dispatch(HttpChannel.java:753), at org.eclipse.jetty.server.HttpChannel.handle(HttpChannel.java:501), at org.eclipse.jetty.server.HttpConnection.onFillable(HttpConnection.java:287), at org.eclipse.jetty.io.AbstractConnection$ReadCallback.succeeded(AbstractConnection.java:314), at org.eclipse.jetty.io.FillInterest.fillable(FillInterest.java:100), at org.eclipse.jetty.io.SelectableChannelEndPoint$1.run(SelectableChannelEndPoint.java:53), at org.eclipse.jetty.util.thread.QueuedThreadPool.runJob(QueuedThreadPool.java:969), at org.eclipse.jetty.util.thread.QueuedThreadPool$Runner.doRunJob(QueuedThreadPool.java:1194), at org.eclipse.jetty.util.thread.QueuedThreadPool$Runner.run(QueuedThreadPool.java:1149), at java.base/java.lang.Thread.run(Thread.java:840),Caused by: javax.mail.MessagingException: Exception reading response;, nested exception is:, java.net.SocketTimeoutException: Read timed out, at com.sun.mail.smtp.SMTPTransport.readServerResponse(SMTPTransport.java:2476), at com.sun.mail.smtp.SMTPTransport.simpleCommand(SMTPTransport.java:2406), at com.sun.mail.smtp.SMTPTransport$LoginAuthenticator.doAuth(SMTPTransport.java:983), at com.sun.mail.smtp.SMTPTransport$Authenticator.authenticate(SMTPTransport.java:924), ... 132 more,Caused by: java.net.SocketTimeoutException: Read timed out, at java.base/sun.nio.ch.NioSocketImpl.timedRead(NioSocketImpl.java:288), at java.base/sun.nio.ch.NioSocketImpl.implRead(NioSocketImpl.java:314), at java.base/sun.nio.ch.NioSocketImpl.read(NioSocketImpl.java:355), at java.base/sun.nio.ch.NioSocketImpl$1.read(NioSocketImpl.java:808), at java.base/java.net.Socket$SocketInputStream.read(Socket.java:966), at java.base/sun.security.ssl.SSLSocketInputRecord.read(SSLSocketInputRecord.java:484), at java.base/sun.security.ssl.SSLSocketInputRecord.readHeader(SSLSocketInputRecord.java:478), at java.base/sun.security.ssl.SSLSocketInputRecord.bytesInCompletePacket(SSLSocketInputRecord.java:70), at java.base/sun.security.ssl.SSLSocketImpl.readApplicationRecord(SSLSocketImpl.java:1465), at java.base/sun.security.ssl.SSLSocketImpl$AppInputStream.read(SSLSocketImpl.java:1069), at com.sun.mail.util.TraceInputStream.read(TraceInputStream.java:102), at java.base/java.io.BufferedInputStream.fill(BufferedInputStream.java:244), at java.base/java.io.BufferedInputStream.read(BufferedInputStream.java:263), at com.sun.mail.util.LineInputStream.readLine(LineInputStream.java:100), at com.sun.mail.smtp.SMTPTransport.readServerResponse(SMTPTransport.java:2456), ... 135 more
[c25a73be-0857-45b9-9e60-9efcdb90a9b3] 2024-06-03T13:56:23+01:00 ERROR metabase.email Error testing SMTP connection,javax.mail.AuthenticationFailedException: ;, nested exception is:, javax.mail.MessagingException: Exception reading response;, nested exception is:, java.net.SocketTimeoutException: Read timed out, at com.sun.mail.smtp.SMTPTransport$Authenticator.authenticate(SMTPTransport.java:942), at com.sun.mail.smtp.SMTPTransport.authenticate(SMTPTransport.java:858), at com.sun.mail.smtp.SMTPTransport.protocolConnect(SMTPTransport.java:762), at javax.mail.Service.connect(Service.java:342), at metabase.email$test_smtp_settings$fn__75838.invoke(email.clj:235), at metabase.email$test_smtp_settings.invokeStatic(email.clj:234), at metabase.email$test_smtp_settings.invoke(email.clj:220), at metabase.email$guess_smtp_security$fn__75843.invoke(email.clj:259), at clojure.core$some.invokeStatic(core.clj:2718), at clojure.core$some.invoke(core.clj:2709), at metabase.email$guess_smtp_security.invokeStatic(email.clj:257), at metabase.email$guess_smtp_security.invoke(email.clj:248), at metabase.email$test_smtp_connection.invokeStatic(email.clj:283), at metabase.email$test_smtp_connection.invoke(email.clj:266), at metabase.api.email$fn__87131.invokeStatic(email.clj:112), at metabase.api.email$fn__87131.invoke(email.clj:92), at compojure.core$wrap_response$fn__44682.invoke(core.clj:160), at compojure.core$wrap_route_middleware$fn__44666.invoke(core.clj:132), at compojure.core$wrap_route_info$fn__44671.invoke(core.clj:139), at compojure.core$wrap_route_matches$fn__44675.invoke(core.clj:151), at clojure.lang.Var.invoke(Var.java:393), at compojure.core$routes$fn__44694$f__44695.invoke(core.clj:198), at compojure.core$routes$fn__44694$f__44695$respond_SINGLEQUOTE___44696.invoke(core.clj:197), at compojure.core$wrap_route_matches$fn__44675.invoke(core.clj:153), at clojure.lang.Var.invoke(Var.java:393), at compojure.core$routes$fn__44694$f__44695.invoke(core.clj:198), at compojure.core$routes$fn__44694.invoke(core.clj:200), at metabase.server.middleware.auth$enforce_authentication$fn__94085.invoke(auth.clj:17), at compojure.core$routes$fn__44694$f__44695.invoke(core.clj:198), at compojure.core$routes$fn__44694.invoke(core.clj:200), at compojure.core$make_context$handler__44722.invoke(core.clj:290), at compojure.core$make_context$fn__44726.invoke(core.clj:300), at compojure.core$routes$fn__44694$f__44695.invoke(core.clj:198), at compojure.core$routes$fn__44694$f__44695$respond_SINGLEQUOTE___44696.invoke(core.clj:197), at compojure.core$make_context$fn__44726.invoke(core.clj:301), at compojure.core$routes$fn__44694$f__44695.invoke(core.clj:198), at compojure.core$routes$fn__44694$f__44695$respond_SINGLEQUOTE___44696.invoke(core.clj:197), at compojure.core$make_context$fn__44726.invoke(core.clj:301), at compojure.core$routes$fn__44694$f__44695.invoke(core.clj:198), at compojure.core$routes$fn__44694$f__44695$respond_SINGLEQUOTE___44696.invoke(core.clj:197), at compojure.core$make_context$fn__44726.invoke(core.clj:301), at compojure.core$routes$fn__44694$f__44695.invoke(core.clj:198), at compojure.core$routes$fn__44694$f__44695$respond_SINGLEQUOTE___44696.invoke(core.clj:197), at compojure.core$make_context$fn__44726.invoke(core.clj:301), at compojure.core$routes$fn__44694$f__44695.invoke(core.clj:198), at compojure.core$routes$fn__44694$f__44695$respond_SINGLEQUOTE___44696.invoke(core.clj:197), at compojure.core$make_context$fn__44726.invoke(core.clj:301), at compojure.core$routes$fn__44694$f__44695.invoke(core.clj:198), at compojure.core$routes$fn__44694$f__44695$respond_SINGLEQUOTE___44696.invoke(core.clj:197), at compojure.core$make_context$fn__44726.invoke(core.clj:301), at compojure.core$routes$fn__44694$f__44695.invoke(core.clj:198), at compojure.core$routes$fn__44694$f__44695$respond_SINGLEQUOTE___44696.invoke(core.clj:197), at compojure.core$make_context$fn__44726.invoke(core.clj:301), at compojure.core$routes$fn__44694$f__44695.invoke(core.clj:198), at compojure.core$routes$fn__44694$f__44695$respond_SINGLEQUOTE___44696.invoke(core.clj:197), at compojure.core$make_context$fn__44726.invoke(core.clj:301), at compojure.core$routes$fn__44694$f__44695.invoke(core.clj:198), at compojure.core$routes$fn__44694$f__44695$respond_SINGLEQUOTE___44696.invoke(core.clj:197), at compojure.core$make_context$fn__44726.invoke(core.clj:301), at compojure.core$routes$fn__44694$f__44695.invoke(core.clj:198), at compojure.core$routes$fn__44694$f__44695$respond_SINGLEQUOTE___44696.invoke(core.clj:197), at compojure.core$make_context$fn__44726.invoke(core.clj:301), at compojure.core$routes$fn__44694$f__44695.invoke(core.clj:198), at compojure.core$routes$fn__44694$f__44695$respond_SINGLEQUOTE___44696.invoke(core.clj:197), at metabase.api.routes$fn__102118$fn__102121.invoke(routes.clj:67), at compojure.core$routes$fn__44694$f__44695.invoke(core.clj:198), at compojure.core$routes$fn__44694.invoke(core.clj:200), at clojure.lang.AFn.applyToHelper(AFn.java:160), at clojure.lang.AFn.applyTo(AFn.java:144), at clojure.core$apply.invokeStatic(core.clj:667), at clojure.core$apply.invoke(core.clj:662), at metabase.server.routes$fn__102283$fn__102284.doInvoke(routes.clj:72), at clojure.lang.RestFn.invoke(RestFn.java:436), at compojure.core$routes$fn__44694$f__44695.invoke(core.clj:198), at compojure.core$routes$fn__44694.invoke(core.clj:200), at compojure.core$make_context$handler__44722.invoke(core.clj:290), at compojure.core$make_context$fn__44726.invoke(core.clj:300), at compojure.core$routes$fn__44694$f__44695.invoke(core.clj:198), at compojure.core$routes$fn__44694$f__44695$respond_SINGLEQUOTE___44696.invoke(core.clj:197), at compojure.core$wrap_route_matches$fn__44675.invoke(core.clj:153), at compojure.core$routes$fn__44694$f__44695.invoke(core.clj:198), at compojure.core$routes$fn__44694$f__44695$respond_SINGLEQUOTE___44696.invoke(core.clj:197), at compojure.core$wrap_route_matches$fn__44675.invoke(core.clj:153), at compojure.core$routes$fn__44694$f__44695.invoke(core.clj:198), at compojure.core$routes$fn__44694$f__44695$respond_SINGLEQUOTE___44696.invoke(core.clj:197), at compojure.core$wrap_route_matches$fn__44675.invoke(core.clj:153), at compojure.core$routes$fn__44694$f__44695.invoke(core.clj:198), at compojure.core$routes$fn__44694$f__44695$respond_SINGLEQUOTE___44696.invoke(core.clj:197), at metabase.server.routes$fn__102268$fn__102270.invoke(routes.clj:49), at compojure.core$routes$fn__44694$f__44695.invoke(core.clj:198), at compojure.core$routes$fn__44694.invoke(core.clj:200), at metabase.server.middleware.exceptions$catch_uncaught_exceptions$fn__98829.invoke(exceptions.clj:108), at metabase.server.middleware.exceptions$catch_api_exceptions$fn__98826.invoke(exceptions.clj:96), at metabase.server.middleware.log$log_api_call$fn__102560$fn__102561$fn__102562.invoke(log.clj:230), at metabase.driver.sql_jdbc.execute.diagnostic$do_with_diagnostic_info.invokeStatic(diagnostic.clj:18), at metabase.driver.sql_jdbc.execute.diagnostic$do_with_diagnostic_info.invoke(diagnostic.clj:12), at metabase.server.middleware.log$log_api_call$fn__102560$fn__102561.invoke(log.clj:222), at toucan2.execute$do_with_call_counts.invokeStatic(execute.clj:112), at toucan2.execute$do_with_call_counts.invoke(execute.clj:103), at metabase.server.middleware.log$log_api_call$fn__102560.invoke(log.clj:221), at metabase.server.middleware.browser_cookie$ensure_browser_id_cookie$fn__104625.invoke(browser_cookie.clj:40), at metabase.server.middleware.security$add_security_headers$fn__98785.invoke(security.clj:182), at metabase.server.middleware.json$wrap_json_body$fn__46039.invoke(json.clj:67), at metabase.server.middleware.offset_paging$handle_paging$fn__84983.invoke(offset_paging.clj:43), at metabase.server.middleware.json$wrap_streamed_json_response$fn__46057.invoke(json.clj:103), at ring.middleware.keyword_params$wrap_keyword_params$fn__104892.invoke(keyword_params.clj:55), at ring.middleware.params$wrap_params$fn__104911.invoke(params.clj:77), at metabase.server.middleware.misc$maybe_set_site_url$fn__67273.invoke(misc.clj:61), at metabase.server.middleware.session$reset_session_timeout$fn__72704.invoke(session.clj:546), at metabase.server.middleware.session$bind_current_user$fn__72670$fn__72671.invoke(session.clj:440), at metabase.server.middleware.session$do_with_current_user.invokeStatic(session.clj:419), at metabase.server.middleware.session$do_with_current_user.invoke(session.clj:403), at metabase.server.middleware.session$bind_current_user$fn__72670.invoke(session.clj:439), at metabase.server.middleware.session$wrap_current_user_info$fn__72653.invoke(session.clj:378), at metabase.server.middleware.session$wrap_session_id$fn__72625.invoke(session.clj:257), at metabase.server.middleware.auth$wrap_static_api_key$fn__94093.invoke(auth.clj:30), at ring.middleware.cookies$wrap_cookies$fn__104812.invoke(cookies.clj:194), at metabase.server.middleware.misc$add_content_type$fn__67255.invoke(misc.clj:29), at metabase.server.middleware.misc$disable_streaming_buffering$fn__67281.invoke(misc.clj:78), at ring.middleware.gzip$wrap_gzip$fn__104854.invoke(gzip.clj:86), at metabase.server.middleware.misc$bind_request$fn__67284.invoke(misc.clj:95), at metabase.server.middleware.ssl$redirect_to_https_middleware$fn__104641.invoke(ssl.clj:51), at metabase.server$async_proxy_handler$fn__67695.invoke(server.clj:78), at metabase.server.proxy$org.eclipse.jetty.server.handler.AbstractHandler$ff19274a.handle(Unknown Source), at org.eclipse.jetty.server.handler.StatisticsHandler.handle(StatisticsHandler.java:173), at org.eclipse.jetty.server.handler.HandlerWrapper.handle(HandlerWrapper.java:122), at org.eclipse.jetty.server.Server.handle(Server.java:563), at org.eclipse.jetty.server.HttpChannel$RequestDispatchable.dispatch(HttpChannel.java:1598), at org.eclipse.jetty.server.HttpChannel.dispatch(HttpChannel.java:753), at org.eclipse.jetty.server.HttpChannel.handle(HttpChannel.java:501), at org.eclipse.jetty.server.HttpConnection.onFillable(HttpConnection.java:287), at org.eclipse.jetty.io.AbstractConnection$ReadCallback.succeeded(AbstractConnection.java:314), at org.eclipse.jetty.io.FillInterest.fillable(FillInterest.java:100), at org.eclipse.jetty.io.SelectableChannelEndPoint$1.run(SelectableChannelEndPoint.java:53), at org.eclipse.jetty.util.thread.QueuedThreadPool.runJob(QueuedThreadPool.java:969), at org.eclipse.jetty.util.thread.QueuedThreadPool$Runner.doRunJob(QueuedThreadPool.java:1194), at org.eclipse.jetty.util.thread.QueuedThreadPool$Runner.run(QueuedThreadPool.java:1149), at java.base/java.lang.Thread.run(Thread.java:840),Caused by: javax.mail.MessagingException: Exception reading response;, nested exception is:, java.net.SocketTimeoutException: Read timed out, at com.sun.mail.smtp.SMTPTransport.readServerResponse(SMTPTransport.java:2476), at com.sun.mail.smtp.SMTPTransport.simpleCommand(SMTPTransport.java:2406), at com.sun.mail.smtp.SMTPTransport$LoginAuthenticator.doAuth(SMTPTransport.java:983), at com.sun.mail.smtp.SMTPTransport$Authenticator.authenticate(SMTPTransport.java:924), ... 137 more,Caused by: java.net.SocketTimeoutException: Read timed out, at java.base/sun.nio.ch.NioSocketImpl.timedRead(NioSocketImpl.java:288), at java.base/sun.nio.ch.NioSocketImpl.implRead(NioSocketImpl.java:314), at java.base/sun.nio.ch.NioSocketImpl.read(NioSocketImpl.java:355), at java.base/sun.nio.ch.NioSocketImpl$1.read(NioSocketImpl.java:808), at java.base/java.net.Socket$SocketInputStream.read(Socket.java:966), at java.base/sun.security.ssl.SSLSocketInputRecord.read(SSLSocketInputRecord.java:484), at java.base/sun.security.ssl.SSLSocketInputRecord.readHeader(SSLSocketInputRecord.java:478), at java.base/sun.security.ssl.SSLSocketInputRecord.bytesInCompletePacket(SSLSocketInputRecord.java:70), at java.base/sun.security.ssl.SSLSocketImpl.readApplicationRecord(SSLSocketImpl.java:1465), at java.base/sun.security.ssl.SSLSocketImpl$AppInputStream.read(SSLSocketImpl.java:1069), at com.sun.mail.util.TraceInputStream.read(TraceInputStream.java:102), at java.base/java.io.BufferedInputStream.fill(BufferedInputStream.java:244), at java.base/java.io.BufferedInputStream.read(BufferedInputStream.java:263), at com.sun.mail.util.LineInputStream.readLine(LineInputStream.java:100), at com.sun.mail.smtp.SMTPTransport.readServerResponse(SMTPTransport.java:2456), ... 140 more
[c25a73be-0857-45b9-9e60-9efcdb90a9b3] 2024-06-03T13:56:29+01:00 ERROR metabase.email Error testing SMTP connection,javax.mail.AuthenticationFailedException: ;, nested exception is:, javax.mail.MessagingException: Exception reading response;, nested exception is:, java.net.SocketTimeoutException: Read timed out, at com.sun.mail.smtp.SMTPTransport$Authenticator.authenticate(SMTPTransport.java:942), at com.sun.mail.smtp.SMTPTransport.authenticate(SMTPTransport.java:858), at com.sun.mail.smtp.SMTPTransport.protocolConnect(SMTPTransport.java:762), at javax.mail.Service.connect(Service.java:342), at metabase.email$test_smtp_settings$fn__75838.invoke(email.clj:235), at metabase.email$test_smtp_settings.invokeStatic(email.clj:234), at metabase.email$test_smtp_settings.invoke(email.clj:220), at metabase.email$guess_smtp_security$fn__75843.invoke(email.clj:259), at clojure.core$some.invokeStatic(core.clj:2718), at clojure.core$some.invoke(core.clj:2709), at metabase.email$guess_smtp_security.invokeStatic(email.clj:257), at metabase.email$guess_smtp_security.invoke(email.clj:248), at metabase.email$test_smtp_connection.invokeStatic(email.clj:283), at metabase.email$test_smtp_connection.invoke(email.clj:266), at metabase.api.email$fn__87131.invokeStatic(email.clj:112), at metabase.api.email$fn__87131.invoke(email.clj:92), at compojure.core$wrap_response$fn__44682.invoke(core.clj:160), at compojure.core$wrap_route_middleware$fn__44666.invoke(core.clj:132), at compojure.core$wrap_route_info$fn__44671.invoke(core.clj:139), at compojure.core$wrap_route_matches$fn__44675.invoke(core.clj:151), at clojure.lang.Var.invoke(Var.java:393), at compojure.core$routes$fn__44694$f__44695.invoke(core.clj:198), at compojure.core$routes$fn__44694$f__44695$respond_SINGLEQUOTE___44696.invoke(core.clj:197), at compojure.core$wrap_route_matches$fn__44675.invoke(core.clj:153), at clojure.lang.Var.invoke(Var.java:393), at compojure.core$routes$fn__44694$f__44695.invoke(core.clj:198), at compojure.core$routes$fn__44694.invoke(core.clj:200), at metabase.server.middleware.auth$enforce_authentication$fn__94085.invoke(auth.clj:17), at compojure.core$routes$fn__44694$f__44695.invoke(core.clj:198), at compojure.core$routes$fn__44694.invoke(core.clj:200), at compojure.core$make_context$handler__44722.invoke(core.clj:290), at compojure.core$make_context$fn__44726.invoke(core.clj:300), at compojure.core$routes$fn__44694$f__44695.invoke(core.clj:198), at compojure.core$routes$fn__44694$f__44695$respond_SINGLEQUOTE___44696.invoke(core.clj:197), at compojure.core$make_context$fn__44726.invoke(core.clj:301), at compojure.core$routes$fn__44694$f__44695.invoke(core.clj:198), at compojure.core$routes$fn__44694$f__44695$respond_SINGLEQUOTE___44696.invoke(core.clj:197), at compojure.core$make_context$fn__44726.invoke(core.clj:301), at compojure.core$routes$fn__44694$f__44695.invoke(core.clj:198), at compojure.core$routes$fn__44694$f__44695$respond_SINGLEQUOTE___44696.invoke(core.clj:197), at compojure.core$make_context$fn__44726.invoke(core.clj:301), at compojure.core$routes$fn__44694$f__44695.invoke(core.clj:198), at compojure.core$routes$fn__44694$f__44695$respond_SINGLEQUOTE___44696.invoke(core.clj:197), at compojure.core$make_context$fn__44726.invoke(core.clj:301), at compojure.core$routes$fn__44694$f__44695.invoke(core.clj:198), at compojure.core$routes$fn__44694$f__44695$respond_SINGLEQUOTE___44696.invoke(core.clj:197), at compojure.core$make_context$fn__44726.invoke(core.clj:301), at compojure.core$routes$fn__44694$f__44695.invoke(core.clj:198), at compojure.core$routes$fn__44694$f__44695$respond_SINGLEQUOTE___44696.invoke(core.clj:197), at compojure.core$make_context$fn__44726.invoke(core.clj:301), at compojure.core$routes$fn__44694$f__44695.invoke(core.clj:198), at compojure.core$routes$fn__44694$f__44695$respond_SINGLEQUOTE___44696.invoke(core.clj:197), at compojure.core$make_context$fn__44726.invoke(core.clj:301), at compojure.core$routes$fn__44694$f__44695.invoke(core.clj:198), at compojure.core$routes$fn__44694$f__44695$respond_SINGLEQUOTE___44696.invoke(core.clj:197), at compojure.core$make_context$fn__44726.invoke(core.clj:301), at compojure.core$routes$fn__44694$f__44695.invoke(core.clj:198), at compojure.core$routes$fn__44694$f__44695$respond_SINGLEQUOTE___44696.invoke(core.clj:197), at compojure.core$make_context$fn__44726.invoke(core.clj:301), at compojure.core$routes$fn__44694$f__44695.invoke(core.clj:198), at compojure.core$routes$fn__44694$f__44695$respond_SINGLEQUOTE___44696.invoke(core.clj:197), at compojure.core$make_context$fn__44726.invoke(core.clj:301), at compojure.core$routes$fn__44694$f__44695.invoke(core.clj:198), at compojure.core$routes$fn__44694$f__44695$respond_SINGLEQUOTE___44696.invoke(core.clj:197), at metabase.api.routes$fn__102118$fn__102121.invoke(routes.clj:67), at compojure.core$routes$fn__44694$f__44695.invoke(core.clj:198), at compojure.core$routes$fn__44694.invoke(core.clj:200), at clojure.lang.AFn.applyToHelper(AFn.java:160), at clojure.lang.AFn.applyTo(AFn.java:144), at clojure.core$apply.invokeStatic(core.clj:667), at clojure.core$apply.invoke(core.clj:662), at metabase.server.routes$fn__102283$fn__102284.doInvoke(routes.clj:72), at clojure.lang.RestFn.invoke(RestFn.java:436), at compojure.core$routes$fn__44694$f__44695.invoke(core.clj:198), at compojure.core$routes$fn__44694.invoke(core.clj:200), at compojure.core$make_context$handler__44722.invoke(core.clj:290), at compojure.core$make_context$fn__44726.invoke(core.clj:300), at compojure.core$routes$fn__44694$f__44695.invoke(core.clj:198), at compojure.core$routes$fn__44694$f__44695$respond_SINGLEQUOTE___44696.invoke(core.clj:197), at compojure.core$wrap_route_matches$fn__44675.invoke(core.clj:153), at compojure.core$routes$fn__44694$f__44695.invoke(core.clj:198), at compojure.core$routes$fn__44694$f__44695$respond_SINGLEQUOTE___44696.invoke(core.clj:197), at compojure.core$wrap_route_matches$fn__44675.invoke(core.clj:153), at compojure.core$routes$fn__44694$f__44695.invoke(core.clj:198), at compojure.core$routes$fn__44694$f__44695$respond_SINGLEQUOTE___44696.invoke(core.clj:197), at compojure.core$wrap_route_matches$fn__44675.invoke(core.clj:153), at compojure.core$routes$fn__44694$f__44695.invoke(core.clj:198), at compojure.core$routes$fn__44694$f__44695$respond_SINGLEQUOTE___44696.invoke(core.clj:197), at metabase.server.routes$fn__102268$fn__102270.invoke(routes.clj:49), at compojure.core$routes$fn__44694$f__44695.invoke(core.clj:198), at compojure.core$routes$fn__44694.invoke(core.clj:200), at metabase.server.middleware.exceptions$catch_uncaught_exceptions$fn__98829.invoke(exceptions.clj:108), at metabase.server.middleware.exceptions$catch_api_exceptions$fn__98826.invoke(exceptions.clj:96), at metabase.server.middleware.log$log_api_call$fn__102560$fn__102561$fn__102562.invoke(log.clj:230), at metabase.driver.sql_jdbc.execute.diagnostic$do_with_diagnostic_info.invokeStatic(diagnostic.clj:18), at metabase.driver.sql_jdbc.execute.diagnostic$do_with_diagnostic_info.invoke(diagnostic.clj:12), at metabase.server.middleware.log$log_api_call$fn__102560$fn__102561.invoke(log.clj:222), at toucan2.execute$do_with_call_counts.invokeStatic(execute.clj:112), at toucan2.execute$do_with_call_counts.invoke(execute.clj:103), at metabase.server.middleware.log$log_api_call$fn__102560.invoke(log.clj:221), at metabase.server.middleware.browser_cookie$ensure_browser_id_cookie$fn__104625.invoke(browser_cookie.clj:40), at metabase.server.middleware.security$add_security_headers$fn__98785.invoke(security.clj:182), at metabase.server.middleware.json$wrap_json_body$fn__46039.invoke(json.clj:67), at metabase.server.middleware.offset_paging$handle_paging$fn__84983.invoke(offset_paging.clj:43), at metabase.server.middleware.json$wrap_streamed_json_response$fn__46057.invoke(json.clj:103), at ring.middleware.keyword_params$wrap_keyword_params$fn__104892.invoke(keyword_params.clj:55), at ring.middleware.params$wrap_params$fn__104911.invoke(params.clj:77), at metabase.server.middleware.misc$maybe_set_site_url$fn__67273.invoke(misc.clj:61), at metabase.server.middleware.session$reset_session_timeout$fn__72704.invoke(session.clj:546), at metabase.server.middleware.session$bind_current_user$fn__72670$fn__72671.invoke(session.clj:440), at metabase.server.middleware.session$do_with_current_user.invokeStatic(session.clj:419), at metabase.server.middleware.session$do_with_current_user.invoke(session.clj:403), at metabase.server.middleware.session$bind_current_user$fn__72670.invoke(session.clj:439), at metabase.server.middleware.session$wrap_current_user_info$fn__72653.invoke(session.clj:378), at metabase.server.middleware.session$wrap_session_id$fn__72625.invoke(session.clj:257), at metabase.server.middleware.auth$wrap_static_api_key$fn__94093.invoke(auth.clj:30), at ring.middleware.cookies$wrap_cookies$fn__104812.invoke(cookies.clj:194), at metabase.server.middleware.misc$add_content_type$fn__67255.invoke(misc.clj:29), at metabase.server.middleware.misc$disable_streaming_buffering$fn__67281.invoke(misc.clj:78), at ring.middleware.gzip$wrap_gzip$fn__104854.invoke(gzip.clj:86), at metabase.server.middleware.misc$bind_request$fn__67284.invoke(misc.clj:95), at metabase.server.middleware.ssl$redirect_to_https_middleware$fn__104641.invoke(ssl.clj:51), at metabase.server$async_proxy_handler$fn__67695.invoke(server.clj:78), at metabase.server.proxy$org.eclipse.jetty.server.handler.AbstractHandler$ff19274a.handle(Unknown Source), at org.eclipse.jetty.server.handler.StatisticsHandler.handle(StatisticsHandler.java:173), at org.eclipse.jetty.server.handler.HandlerWrapper.handle(HandlerWrapper.java:122), at org.eclipse.jetty.server.Server.handle(Server.java:563), at org.eclipse.jetty.server.HttpChannel$RequestDispatchable.dispatch(HttpChannel.java:1598), at org.eclipse.jetty.server.HttpChannel.dispatch(HttpChannel.java:753), at org.eclipse.jetty.server.HttpChannel.handle(HttpChannel.java:501), at org.eclipse.jetty.server.HttpConnection.onFillable(HttpConnection.java:287), at org.eclipse.jetty.io.AbstractConnection$ReadCallback.succeeded(AbstractConnection.java:314), at org.eclipse.jetty.io.FillInterest.fillable(FillInterest.java:100), at org.eclipse.jetty.io.SelectableChannelEndPoint$1.run(SelectableChannelEndPoint.java:53), at org.eclipse.jetty.util.thread.QueuedThreadPool.runJob(QueuedThreadPool.java:969), at org.eclipse.jetty.util.thread.QueuedThreadPool$Runner.doRunJob(QueuedThreadPool.java:1194), at org.eclipse.jetty.util.thread.QueuedThreadPool$Runner.run(QueuedThreadPool.java:1149), at java.base/java.lang.Thread.run(Thread.java:840),Caused by: javax.mail.MessagingException: Exception reading response;, nested exception is:, java.net.SocketTimeoutException: Read timed out, at com.sun.mail.smtp.SMTPTransport.readServerResponse(SMTPTransport.java:2476), at com.sun.mail.smtp.SMTPTransport.simpleCommand(SMTPTransport.java:2406), at com.sun.mail.smtp.SMTPTransport$LoginAuthenticator.doAuth(SMTPTransport.java:983), at com.sun.mail.smtp.SMTPTransport$Authenticator.authenticate(SMTPTransport.java:924), ... 137 more,Caused by: java.net.SocketTimeoutException: Read timed out, at java.base/sun.nio.ch.NioSocketImpl.timedRead(NioSocketImpl.java:288), at java.base/sun.nio.ch.NioSocketImpl.implRead(NioSocketImpl.java:314), at java.base/sun.nio.ch.NioSocketImpl.read(NioSocketImpl.java:355), at java.base/sun.nio.ch.NioSocketImpl$1.read(NioSocketImpl.java:808), at java.base/java.net.Socket$SocketInputStream.read(Socket.java:966), at java.base/sun.security.ssl.SSLSocketInputRecord.read(SSLSocketInputRecord.java:484), at java.base/sun.security.ssl.SSLSocketInputRecord.readHeader(SSLSocketInputRecord.java:478), at java.base/sun.security.ssl.SSLSocketInputRecord.bytesInCompletePacket(SSLSocketInputRecord.java:70), at java.base/sun.security.ssl.SSLSocketImpl.readApplicationRecord(SSLSocketImpl.java:1465), at java.base/sun.security.ssl.SSLSocketImpl$AppInputStream.read(SSLSocketImpl.java:1069), at com.sun.mail.util.TraceInputStream.read(TraceInputStream.java:102), at java.base/java.io.BufferedInputStream.fill(BufferedInputStream.java:244), at java.base/java.io.BufferedInputStream.read(BufferedInputStream.java:263), at com.sun.mail.util.LineInputStream.readLine(LineInputStream.java:100), at com.sun.mail.smtp.SMTPTransport.readServerResponse(SMTPTransport.java:2456), ... 140 more
[c25a73be-0857-45b9-9e60-9efcdb90a9b3] 2024-06-03T13:56:30+01:00 ERROR metabase.email Error testing SMTP connection,javax.mail.MessagingException: Could not connect to SMTP host: smtp-mail.outlook.com, port: 587;, nested exception is:, javax.net.ssl.SSLException: Unsupported or unrecognized SSL message, at com.sun.mail.smtp.SMTPTransport.openServer(SMTPTransport.java:2212), at com.sun.mail.smtp.SMTPTransport.protocolConnect(SMTPTransport.java:722), at javax.mail.Service.connect(Service.java:342), at metabase.email$test_smtp_settings$fn__75838.invoke(email.clj:235), at metabase.email$test_smtp_settings.invokeStatic(email.clj:234), at metabase.email$test_smtp_settings.invoke(email.clj:220), at metabase.email$guess_smtp_security$fn__75843.invoke(email.clj:259), at clojure.core$some.invokeStatic(core.clj:2718), at clojure.core$some.invoke(core.clj:2709), at metabase.email$guess_smtp_security.invokeStatic(email.clj:257), at metabase.email$guess_smtp_security.invoke(email.clj:248), at metabase.email$test_smtp_connection.invokeStatic(email.clj:283), at metabase.email$test_smtp_connection.invoke(email.clj:266), at metabase.api.email$fn__87131.invokeStatic(email.clj:112), at metabase.api.email$fn__87131.invoke(email.clj:92), at compojure.core$wrap_response$fn__44682.invoke(core.clj:160), at compojure.core$wrap_route_middleware$fn__44666.invoke(core.clj:132), at compojure.core$wrap_route_info$fn__44671.invoke(core.clj:139), at compojure.core$wrap_route_matches$fn__44675.invoke(core.clj:151), at clojure.lang.Var.invoke(Var.java:393), at compojure.core$routes$fn__44694$f__44695.invoke(core.clj:198), at compojure.core$routes$fn__44694$f__44695$respond_SINGLEQUOTE___44696.invoke(core.clj:197), at compojure.core$wrap_route_matches$fn__44675.invoke(core.clj:153), at clojure.lang.Var.invoke(Var.java:393), at compojure.core$routes$fn__44694$f__44695.invoke(core.clj:198), at compojure.core$routes$fn__44694.invoke(core.clj:200), at metabase.server.middleware.auth$enforce_authentication$fn__94085.invoke(auth.clj:17), at compojure.core$routes$fn__44694$f__44695.invoke(core.clj:198), at compojure.core$routes$fn__44694.invoke(core.clj:200), at compojure.core$make_context$handler__44722.invoke(core.clj:290), at compojure.core$make_context$fn__44726.invoke(core.clj:300), at compojure.core$routes$fn__44694$f__44695.invoke(core.clj:198), at compojure.core$routes$fn__44694$f__44695$respond_SINGLEQUOTE___44696.invoke(core.clj:197), at compojure.core$make_context$fn__44726.invoke(core.clj:301), at compojure.core$routes$fn__44694$f__44695.invoke(core.clj:198), at compojure.core$routes$fn__44694$f__44695$respond_SINGLEQUOTE___44696.invoke(core.clj:197), at compojure.core$make_context$fn__44726.invoke(core.clj:301), at compojure.core$routes$fn__44694$f__44695.invoke(core.clj:198), at compojure.core$routes$fn__44694$f__44695$respond_SINGLEQUOTE___44696.invoke(core.clj:197), at compojure.core$make_context$fn__44726.invoke(core.clj:301), at compojure.core$routes$fn__44694$f__44695.invoke(core.clj:198), at compojure.core$routes$fn__44694$f__44695$respond_SINGLEQUOTE___44696.invoke(core.clj:197), at compojure.core$make_context$fn__44726.invoke(core.clj:301), at compojure.core$routes$fn__44694$f__44695.invoke(core.clj:198), at compojure.core$routes$fn__44694$f__44695$respond_SINGLEQUOTE___44696.invoke(core.clj:197), at compojure.core$make_context$fn__44726.invoke(core.clj:301), at compojure.core$routes$fn__44694$f__44695.invoke(core.clj:198), at compojure.core$routes$fn__44694$f__44695$respond_SINGLEQUOTE___44696.invoke(core.clj:197), at compojure.core$make_context$fn__44726.invoke(core.clj:301), at compojure.core$routes$fn__44694$f__44695.invoke(core.clj:198), at compojure.core$routes$fn__44694$f__44695$respond_SINGLEQUOTE___44696.invoke(core.clj:197), at compojure.core$make_context$fn__44726.invoke(core.clj:301), at compojure.core$routes$fn__44694$f__44695.invoke(core.clj:198), at compojure.core$routes$fn__44694$f__44695$respond_SINGLEQUOTE___44696.invoke(core.clj:197), at compojure.core$make_context$fn__44726.invoke(core.clj:301), at compojure.core$routes$fn__44694$f__44695.invoke(core.clj:198), at compojure.core$routes$fn__44694$f__44695$respond_SINGLEQUOTE___44696.invoke(core.clj:197), at compojure.core$make_context$fn__44726.invoke(core.clj:301), at compojure.core$routes$fn__44694$f__44695.invoke(core.clj:198), at compojure.core$routes$fn__44694$f__44695$respond_SINGLEQUOTE___44696.invoke(core.clj:197), at compojure.core$make_context$fn__44726.invoke(core.clj:301), at compojure.core$routes$fn__44694$f__44695.invoke(core.clj:198), at compojure.core$routes$fn__44694$f__44695$respond_SINGLEQUOTE___44696.invoke(core.clj:197), at metabase.api.routes$fn__102118$fn__102121.invoke(routes.clj:67), at compojure.core$routes$fn__44694$f__44695.invoke(core.clj:198), at compojure.core$routes$fn__44694.invoke(core.clj:200), at clojure.lang.AFn.applyToHelper(AFn.java:160), at clojure.lang.AFn.applyTo(AFn.java:144), at clojure.core$apply.invokeStatic(core.clj:667), at clojure.core$apply.invoke(core.clj:662), at metabase.server.routes$fn__102283$fn__102284.doInvoke(routes.clj:72), at clojure.lang.RestFn.invoke(RestFn.java:436), at compojure.core$routes$fn__44694$f__44695.invoke(core.clj:198), at compojure.core$routes$fn__44694.invoke(core.clj:200), at compojure.core$make_context$handler__44722.invoke(core.clj:290), at compojure.core$make_context$fn__44726.invoke(core.clj:300), at compojure.core$routes$fn__44694$f__44695.invoke(core.clj:198), at compojure.core$routes$fn__44694$f__44695$respond_SINGLEQUOTE___44696.invoke(core.clj:197), at compojure.core$wrap_route_matches$fn__44675.invoke(core.clj:153), at compojure.core$routes$fn__44694$f__44695.invoke(core.clj:198), at compojure.core$routes$fn__44694$f__44695$respond_SINGLEQUOTE___44696.invoke(core.clj:197), at compojure.core$wrap_route_matches$fn__44675.invoke(core.clj:153), at compojure.core$routes$fn__44694$f__44695.invoke(core.clj:198), at compojure.core$routes$fn__44694$f__44695$respond_SINGLEQUOTE___44696.invoke(core.clj:197), at compojure.core$wrap_route_matches$fn__44675.invoke(core.clj:153), at compojure.core$routes$fn__44694$f__44695.invoke(core.clj:198), at compojure.core$routes$fn__44694$f__44695$respond_SINGLEQUOTE___44696.invoke(core.clj:197), at metabase.server.routes$fn__102268$fn__102270.invoke(routes.clj:49), at compojure.core$routes$fn__44694$f__44695.invoke(core.clj:198), at compojure.core$routes$fn__44694.invoke(core.clj:200), at metabase.server.middleware.exceptions$catch_uncaught_exceptions$fn__98829.invoke(exceptions.clj:108), at metabase.server.middleware.exceptions$catch_api_exceptions$fn__98826.invoke(exceptions.clj:96), at metabase.server.middleware.log$log_api_call$fn__102560$fn__102561$fn__102562.invoke(log.clj:230), at metabase.driver.sql_jdbc.execute.diagnostic$do_with_diagnostic_info.invokeStatic(diagnostic.clj:18), at metabase.driver.sql_jdbc.execute.diagnostic$do_with_diagnostic_info.invoke(diagnostic.clj:12), at metabase.server.middleware.log$log_api_call$fn__102560$fn__102561.invoke(log.clj:222), at toucan2.execute$do_with_call_counts.invokeStatic(execute.clj:112), at toucan2.execute$do_with_call_counts.invoke(execute.clj:103), at metabase.server.middleware.log$log_api_call$fn__102560.invoke(log.clj:221), at metabase.server.middleware.browser_cookie$ensure_browser_id_cookie$fn__104625.invoke(browser_cookie.clj:40), at metabase.server.middleware.security$add_security_headers$fn__98785.invoke(security.clj:182), at metabase.server.middleware.json$wrap_json_body$fn__46039.invoke(json.clj:67), at metabase.server.middleware.offset_paging$handle_paging$fn__84983.invoke(offset_paging.clj:43), at metabase.server.middleware.json$wrap_streamed_json_response$fn__46057.invoke(json.clj:103), at ring.middleware.keyword_params$wrap_keyword_params$fn__104892.invoke(keyword_params.clj:55), at ring.middleware.params$wrap_params$fn__104911.invoke(params.clj:77), at metabase.server.middleware.misc$maybe_set_site_url$fn__67273.invoke(misc.clj:61), at metabase.server.middleware.session$reset_session_timeout$fn__72704.invoke(session.clj:546), at metabase.server.middleware.session$bind_current_user$fn__72670$fn__72671.invoke(session.clj:440), at metabase.server.middleware.session$do_with_current_user.invokeStatic(session.clj:419), at metabase.server.middleware.session$do_with_current_user.invoke(session.clj:403), at metabase.server.middleware.session$bind_current_user$fn__72670.invoke(session.clj:439), at metabase.server.middleware.session$wrap_current_user_info$fn__72653.invoke(session.clj:378), at metabase.server.middleware.session$wrap_session_id$fn__72625.invoke(session.clj:257), at metabase.server.middleware.auth$wrap_static_api_key$fn__94093.invoke(auth.clj:30), at ring.middleware.cookies$wrap_cookies$fn__104812.invoke(cookies.clj:194), at metabase.server.middleware.misc$add_content_type$fn__67255.invoke(misc.clj:29), at metabase.server.middleware.misc$disable_streaming_buffering$fn__67281.invoke(misc.clj:78), at ring.middleware.gzip$wrap_gzip$fn__104854.invoke(gzip.clj:86), at metabase.server.middleware.misc$bind_request$fn__67284.invoke(misc.clj:95), at metabase.server.middleware.ssl$redirect_to_https_middleware$fn__104641.invoke(ssl.clj:51), at metabase.server$async_proxy_handler$fn__67695.invoke(server.clj:78), at metabase.server.proxy$org.eclipse.jetty.server.handler.AbstractHandler$ff19274a.handle(Unknown Source), at org.eclipse.jetty.server.handler.StatisticsHandler.handle(StatisticsHandler.java:173), at org.eclipse.jetty.server.handler.HandlerWrapper.handle(HandlerWrapper.java:122), at org.eclipse.jetty.server.Server.handle(Server.java:563), at org.eclipse.jetty.server.HttpChannel$RequestDispatchable.dispatch(HttpChannel.java:1598), at org.eclipse.jetty.server.HttpChannel.dispatch(HttpChannel.java:753), at org.eclipse.jetty.server.HttpChannel.handle(HttpChannel.java:501), at org.eclipse.jetty.server.HttpConnection.onFillable(HttpConnection.java:287), at org.eclipse.jetty.io.AbstractConnection$ReadCallback.succeeded(AbstractConnection.java:314), at org.eclipse.jetty.io.FillInterest.fillable(FillInterest.java:100), at org.eclipse.jetty.io.SelectableChannelEndPoint$1.run(SelectableChannelEndPoint.java:53), at org.eclipse.jetty.util.thread.QueuedThreadPool.runJob(QueuedThreadPool.java:969), at org.eclipse.jetty.util.thread.QueuedThreadPool$Runner.doRunJob(QueuedThreadPool.java:1194), at org.eclipse.jetty.util.thread.QueuedThreadPool$Runner.run(QueuedThreadPool.java:1149), at java.base/java.lang.Thread.run(Thread.java:840),Caused by: javax.net.ssl.SSLException: Unsupported or unrecognized SSL message, at java.base/sun.security.ssl.SSLSocketInputRecord.handleUnknownRecord(SSLSocketInputRecord.java:457), at java.base/sun.security.ssl.SSLSocketInputRecord.decode(SSLSocketInputRecord.java:175), at java.base/sun.security.ssl.SSLTransport.decode(SSLTransport.java:111), at java.base/sun.security.ssl.SSLSocketImpl.decode(SSLSocketImpl.java:1510), at java.base/sun.security.ssl.SSLSocketImpl.readHandshakeRecord(SSLSocketImpl.java:1425), at java.base/sun.security.ssl.SSLSocketImpl.startHandshake(SSLSocketImpl.java:455), at java.base/sun.security.ssl.SSLSocketImpl.startHandshake(SSLSocketImpl.java:426), at com.sun.mail.util.SocketFetcher.configureSSLSocket(SocketFetcher.java:602), at com.sun.mail.util.SocketFetcher.createSocket(SocketFetcher.java:376), at com.sun.mail.util.SocketFetcher.getSocket(SocketFetcher.java:214), at com.sun.mail.smtp.SMTPTransport.openServer(SMTPTransport.java:2160), ... 136 more
[c25a73be-0857-45b9-9e60-9efcdb90a9b3] 2024-06-03T13:56:30+01:00 WARN metabase.api.email Problem connecting to mail server: : Exception reading response: Read timed out
[c25a73be-0857-45b9-9e60-9efcdb90a9b3] 2024-06-03T13:56:30+01:00 DEBUG metabase.server.middleware.log PUT /api/email 400 17.8 s (0 DB calls)
{:errors {:email-smtp-username "Wrong username or password", :email-smtp-password "Wrong username or password"}}

Any help would be greatly appreciated

Can you verify that your user name and password are correct? Also, can you verify that authentication password is re/filled by the user account with authenticated SMTP Marked/Enabled? To do so follow these steps to set up SMTP authentication:

  • Go to Admin.Microsoft.com
  • Log in with a security Admin, Global Admin
  • Expand Users > Active Users
  • Click the User that will connect as SMTP
  • Click the Mail Tab
  • Click on Manage Email Apps
  • Make sure that Authenticated SMTP is Marked/Enabled

Enable or disable SMTP AUTH in Exchange Online | Microsoft Learn

Are you following the OAuth 2.0 requirements?

I gave up with MS SMTP. Always seems to be something wrong.
I just use a free account with SMTP2GO. Even if I were to go over the free usage, it's not expensive.
Alternatively, just create an SMTP server that is restricted by IP address of sender. Don't forget to add the IP of the SMTP server to your SPF record.

Hi, I've checked this settings and they are all correct, and still does not connect

Thanks Andrew

Check Can't send emails using smtp with Office 365 · Issue #34229 · metabase/metabase · GitHub and Cannot configure smtp for outgoing email through Office365 · Issue #4272 · metabase/metabase · GitHub