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spring-mail 3.2.5 intermittent error from HELO/EHLO #44646

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yangzii0920 opened this issue Mar 7, 2025 · 4 comments
Closed

spring-mail 3.2.5 intermittent error from HELO/EHLO #44646

yangzii0920 opened this issue Mar 7, 2025 · 4 comments

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@yangzii0920
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yangzii0920 commented Mar 7, 2025 •
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Error description

Hello spring boot team,

I noticed intermittent error from my spring boot application that uses spring mail. When it sends mail, it sends HELO to 0:0:0:0:0:0:0:1, which is not the mail server configured and resulted in error 501 EHLO requires valid address, even though it also logs SMTP: connected to host <my mail server>. (see screenshot)
Image

I would get similar error caused by HELO from actuator health getting mail health:

jakarta.mail.MessagingException: [EOF]
	at org.eclipse.angus.mail.smtp.SMTPTransport.issueCommand(SMTPTransport.java:2373) ~[jakarta.mail-2.0.3.jar:na]
	at org.eclipse.angus.mail.smtp.SMTPTransport.helo(SMTPTransport.java:1666) ~[jakarta.mail-2.0.3.jar:na]
	at org.eclipse.angus.mail.smtp.SMTPTransport.protocolConnect(SMTPTransport.java:735) ~[jakarta.mail-2.0.3.jar:na]
	at jakarta.mail.Service.connect(Service.java:342) ~[jakarta.jakartaee-api-10.0.0.jar:na]
	at org.springframework.mail.javamail.JavaMailSenderImpl.connectTransport(JavaMailSenderImpl.java:480) ~[spring-context-support-6.1.6.jar:6.1.6]
	at org.springframework.mail.javamail.JavaMailSenderImpl.testConnection(JavaMailSenderImpl.java:360) ~[spring-context-support-6.1.6.jar:6.1.6]
	at org.springframework.boot.actuate.mail.MailHealthIndicator.doHealthCheck(MailHealthIndicator.java:52) ~[spring-boot-actuator-3.2.5.jar:3.2.5]
	at org.springframework.boot.actuate.health.AbstractHealthIndicator.health(AbstractHealthIndicator.java:82) ~[spring-boot-actuator-3.2.5.jar:3.2.5]
	at org.springframework.boot.actuate.health.HealthIndicator.getHealth(HealthIndicator.java:37) ~[spring-boot-actuator-3.2.5.jar:3.2.5]
	at org.springframework.boot.actuate.health.HealthEndpointWebExtension.getHealth(HealthEndpointWebExtension.java:94) ~[spring-boot-actuator-3.2.5.jar:3.2.5]
	at org.springframework.boot.actuate.health.HealthEndpointWebExtension.getHealth(HealthEndpointWebExtension.java:47) ~[spring-boot-actuator-3.2.5.jar:3.2.5]
	at org.springframework.boot.actuate.health.HealthEndpointSupport.getLoggedHealth(HealthEndpointSupport.java:172) ~[spring-boot-actuator-3.2.5.jar:3.2.5]
	at org.springframework.boot.actuate.health.HealthEndpointSupport.getContribution(HealthEndpointSupport.java:145) ~[spring-boot-actuator-3.2.5.jar:3.2.5]
	at org.springframework.boot.actuate.health.HealthEndpointSupport.getAggregateContribution(HealthEndpointSupport.java:156) ~[spring-boot-actuator-3.2.5.jar:3.2.5]
	at org.springframework.boot.actuate.health.HealthEndpointSupport.getContribution(HealthEndpointSupport.java:141) ~[spring-boot-actuator-3.2.5.jar:3.2.5]
	at org.springframework.boot.actuate.health.HealthEndpointSupport.getHealth(HealthEndpointSupport.java:110) ~[spring-boot-actuator-3.2.5.jar:3.2.5]
	at org.springframework.boot.actuate.health.HealthEndpointSupport.getHealth(HealthEndpointSupport.java:81) ~[spring-boot-actuator-3.2.5.jar:3.2.5]
	at org.springframework.boot.actuate.health.HealthEndpointWebExtension.health(HealthEndpointWebExtension.java:80) ~[spring-boot-actuator-3.2.5.jar:3.2.5]
	at org.springframework.boot.actuate.health.HealthEndpointWebExtension.health(HealthEndpointWebExtension.java:69) ~[spring-boot-actuator-3.2.5.jar:3.2.5]
	at java.base/jdk.internal.reflect.NativeMethodAccessorImpl.invoke0(Native Method) ~[na:na]
	at java.base/jdk.internal.reflect.NativeMethodAccessorImpl.invoke(Unknown Source) ~[na:na]
	at java.base/jdk.internal.reflect.DelegatingMethodAccessorImpl.invoke(Unknown Source) ~[na:na]
	at java.base/java.lang.reflect.Method.invoke(Unknown Source) ~[na:na]
	at org.springframework.util.ReflectionUtils.invokeMethod(ReflectionUtils.java:281) ~[spring-core-6.1.6.jar:6.1.6]
	at org.springframework.boot.actuate.endpoint.invoke.reflect.ReflectiveOperationInvoker.invoke(ReflectiveOperationInvoker.java:74) ~[spring-boot-actuator-3.2.5.jar:3.2.5]
	at org.springframework.boot.actuate.endpoint.annotation.AbstractDiscoveredOperation.invoke(AbstractDiscoveredOperation.java:60) ~[spring-boot-actuator-3.2.5.jar:3.2.5]
	at org.springframework.boot.actuate.endpoint.web.servlet.AbstractWebMvcEndpointHandlerMapping$ServletWebOperationAdapter.handle(AbstractWebMvcEndpointHandlerMapping.java:327) ~[spring-boot-actuator-3.2.5.jar:3.2.5]
	at org.springframework.boot.actuate.endpoint.web.servlet.AbstractWebMvcEndpointHandlerMapping$OperationHandler.handle(AbstractWebMvcEndpointHandlerMapping.java:434) ~[spring-boot-actuator-3.2.5.jar:3.2.5]
	at java.base/jdk.internal.reflect.NativeMethodAccessorImpl.invoke0(Native Method) ~[na:na]
	at java.base/jdk.internal.reflect.NativeMethodAccessorImpl.invoke(Unknown Source) ~[na:na]
	at java.base/jdk.internal.reflect.DelegatingMethodAccessorImpl.invoke(Unknown Source) ~[na:na]
	at java.base/java.lang.reflect.Method.invoke(Unknown Source) ~[na:na]
	at org.springframework.web.method.support.InvocableHandlerMethod.doInvoke(InvocableHandlerMethod.java:255) ~[spring-web-6.1.6.jar:6.1.6]
	at org.springframework.web.method.support.InvocableHandlerMethod.invokeForRequest(InvocableHandlerMethod.java:188) ~[spring-web-6.1.6.jar:6.1.6]
	at org.springframework.web.servlet.mvc.method.annotation.ServletInvocableHandlerMethod.invokeAndHandle(ServletInvocableHandlerMethod.java:118) ~[spring-webmvc-6.1.6.jar:6.1.6]
	at org.springframework.web.servlet.mvc.method.annotation.RequestMappingHandlerAdapter.invokeHandlerMethod(RequestMappingHandlerAdapter.java:926) ~[spring-webmvc-6.1.6.jar:6.1.6]
	at org.springframework.web.servlet.mvc.method.annotation.RequestMappingHandlerAdapter.handleInternal(RequestMappingHandlerAdapter.java:831) ~[spring-webmvc-6.1.6.jar:6.1.6]
	at org.springframework.web.servlet.mvc.method.AbstractHandlerMethodAdapter.handle(AbstractHandlerMethodAdapter.java:87) ~[spring-webmvc-6.1.6.jar:6.1.6]
	at org.springframework.web.servlet.DispatcherServlet.doDispatch(DispatcherServlet.java:1089) ~[spring-webmvc-6.1.6.jar:6.1.6]
	at org.springframework.web.servlet.DispatcherServlet.doService(DispatcherServlet.java:979) ~[spring-webmvc-6.1.6.jar:6.1.6]
	at org.springframework.web.servlet.FrameworkServlet.processRequest(FrameworkServlet.java:1014) ~[spring-webmvc-6.1.6.jar:6.1.6]
	at org.springframework.web.servlet.FrameworkServlet.doGet(FrameworkServlet.java:903) ~[spring-webmvc-6.1.6.jar:6.1.6]
	at jakarta.servlet.http.HttpServlet.service(HttpServlet.java:527) ~[jakarta.jakartaee-api-10.0.0.jar:na]
	at org.springframework.web.servlet.FrameworkServlet.service(FrameworkServlet.java:885) ~[spring-webmvc-6.1.6.jar:6.1.6]
	at jakarta.servlet.http.HttpServlet.service(HttpServlet.java:614) ~[jakarta.jakartaee-api-10.0.0.jar:na]
	at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:206) ~[tomcat-embed-core-10.1.20.jar:10.1.20]
	at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:150) ~[tomcat-embed-core-10.1.20.jar:10.1.20]
	at org.apache.tomcat.websocket.server.WsFilter.doFilter(WsFilter.java:51) ~[tomcat-embed-websocket-10.1.20.jar:10.1.20]
	at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:175) ~[tomcat-embed-core-10.1.20.jar:10.1.20]
	at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:150) ~[tomcat-embed-core-10.1.20.jar:10.1.20]
	at com.ford.cybersecurity.lookupportal.configuration.TraceIdObservationFilter.doFilterInternal(TraceIdObservationFilter.kt:32) ~[classes/:na]
	at org.springframework.web.filter.OncePerRequestFilter.doFilter(OncePerRequestFilter.java:116) ~[spring-web-6.1.6.jar:6.1.6]
	at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:175) ~[tomcat-embed-core-10.1.20.jar:10.1.20]
	at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:150) ~[tomcat-embed-core-10.1.20.jar:10.1.20]
	at org.springframework.web.filter.CompositeFilter$VirtualFilterChain.doFilter(CompositeFilter.java:108) ~[spring-web-6.1.6.jar:6.1.6]
	at org.springframework.security.web.FilterChainProxy.lambda$doFilterInternal$3(FilterChainProxy.java:231) ~[spring-security-web-6.2.4.jar:6.2.4]
	at org.springframework.security.web.ObservationFilterChainDecorator$FilterObservation$SimpleFilterObservation.lambda$wrap$1(ObservationFilterChainDecorator.java:479) ~[spring-security-web-6.2.4.jar:6.2.4]
	at org.springframework.security.web.ObservationFilterChainDecorator$AroundFilterObservation$SimpleAroundFilterObservation.lambda$wrap$1(ObservationFilterChainDecorator.java:340) ~[spring-security-web-6.2.4.jar:6.2.4]
	at org.springframework.security.web.ObservationFilterChainDecorator.lambda$wrapSecured$0(ObservationFilterChainDecorator.java:82) ~[spring-security-web-6.2.4.jar:6.2.4]
	at org.springframework.security.web.ObservationFilterChainDecorator$VirtualFilterChain.doFilter(ObservationFilterChainDecorator.java:128) ~[spring-security-web-6.2.4.jar:6.2.4]
	at org.springframework.security.web.access.intercept.AuthorizationFilter.doFilter(AuthorizationFilter.java:100) ~[spring-security-web-6.2.4.jar:6.2.4]
	at org.springframework.security.web.ObservationFilterChainDecorator$ObservationFilter.wrapFilter(ObservationFilterChainDecorator.java:240) ~[spring-security-web-6.2.4.jar:6.2.4]
	at org.springframework.security.web.ObservationFilterChainDecorator$ObservationFilter.doFilter(ObservationFilterChainDecorator.java:227) ~[spring-security-web-6.2.4.jar:6.2.4]
	at org.springframework.security.web.ObservationFilterChainDecorator$VirtualFilterChain.doFilter(ObservationFilterChainDecorator.java:137) ~[spring-security-web-6.2.4.jar:6.2.4]
	at org.springframework.security.web.access.ExceptionTranslationFilter.doFilter(ExceptionTranslationFilter.java:126) ~[spring-security-web-6.2.4.jar:6.2.4]
	at org.springframework.security.web.access.ExceptionTranslationFilter.doFilter(ExceptionTranslationFilter.java:120) ~[spring-security-web-6.2.4.jar:6.2.4]
	at org.springframework.security.web.ObservationFilterChainDecorator$ObservationFilter.wrapFilter(ObservationFilterChainDecorator.java:240) ~[spring-security-web-6.2.4.jar:6.2.4]
	at org.springframework.security.web.ObservationFilterChainDecorator$ObservationFilter.doFilter(ObservationFilterChainDecorator.java:227) ~[spring-security-web-6.2.4.jar:6.2.4]
	at org.springframework.security.web.ObservationFilterChainDecorator$VirtualFilterChain.doFilter(ObservationFilterChainDecorator.java:137) ~[spring-security-web-6.2.4.jar:6.2.4]
	at org.springframework.security.web.session.SessionManagementFilter.doFilter(SessionManagementFilter.java:131) ~[spring-security-web-6.2.4.jar:6.2.4]
	at org.springframework.security.web.session.SessionManagementFilter.doFilter(SessionManagementFilter.java:85) ~[spring-security-web-6.2.4.jar:6.2.4]
	at org.springframework.security.web.ObservationFilterChainDecorator$ObservationFilter.wrapFilter(ObservationFilterChainDecorator.java:240) ~[spring-security-web-6.2.4.jar:6.2.4]
	at org.springframework.security.web.ObservationFilterChainDecorator$ObservationFilter.doFilter(ObservationFilterChainDecorator.java:227) ~[spring-security-web-6.2.4.jar:6.2.4]
	at org.springframework.security.web.ObservationFilterChainDecorator$VirtualFilterChain.doFilter(ObservationFilterChainDecorator.java:137) ~[spring-security-web-6.2.4.jar:6.2.4]
	at org.springframework.security.web.authentication.AnonymousAuthenticationFilter.doFilter(AnonymousAuthenticationFilter.java:100) ~[spring-security-web-6.2.4.jar:6.2.4]
	at org.springframework.security.web.ObservationFilterChainDecorator$ObservationFilter.wrapFilter(ObservationFilterChainDecorator.java:240) ~[spring-security-web-6.2.4.jar:6.2.4]
	at org.springframework.security.web.ObservationFilterChainDecorator$ObservationFilter.doFilter(ObservationFilterChainDecorator.java:227) ~[spring-security-web-6.2.4.jar:6.2.4]
	at org.springframework.security.web.ObservationFilterChainDecorator$VirtualFilterChain.doFilter(ObservationFilterChainDecorator.java:137) ~[spring-security-web-6.2.4.jar:6.2.4]
	at org.springframework.security.web.servletapi.SecurityContextHolderAwareRequestFilter.doFilter(SecurityContextHolderAwareRequestFilter.java:179) ~[spring-security-web-6.2.4.jar:6.2.4]
	at org.springframework.security.web.ObservationFilterChainDecorator$ObservationFilter.wrapFilter(ObservationFilterChainDecorator.java:240) ~[spring-security-web-6.2.4.jar:6.2.4]
	at org.springframework.security.web.ObservationFilterChainDecorator$ObservationFilter.doFilter(ObservationFilterChainDecorator.java:227) ~[spring-security-web-6.2.4.jar:6.2.4]
	at org.springframework.security.web.ObservationFilterChainDecorator$VirtualFilterChain.doFilter(ObservationFilterChainDecorator.java:137) ~[spring-security-web-6.2.4.jar:6.2.4]
	at org.springframework.security.web.savedrequest.RequestCacheAwareFilter.doFilter(RequestCacheAwareFilter.java:63) ~[spring-security-web-6.2.4.jar:6.2.4]
	at org.springframework.security.web.ObservationFilterChainDecorator$ObservationFilter.wrapFilter(ObservationFilterChainDecorator.java:240) ~[spring-security-web-6.2.4.jar:6.2.4]
	at org.springframework.security.web.ObservationFilterChainDecorator$ObservationFilter.doFilter(ObservationFilterChainDecorator.java:227) ~[spring-security-web-6.2.4.jar:6.2.4]
	at org.springframework.security.web.ObservationFilterChainDecorator$VirtualFilterChain.doFilter(ObservationFilterChainDecorator.java:137) ~[spring-security-web-6.2.4.jar:6.2.4]
	at com.ford.cybersecurity.lookupportal.security.ResponseFilter.doFilter(ResponseFilter.kt:18) ~[classes/:na]
	at org.springframework.security.web.ObservationFilterChainDecorator$ObservationFilter.wrapFilter(ObservationFilterChainDecorator.java:240) ~[spring-security-web-6.2.4.jar:6.2.4]
	at org.springframework.security.web.ObservationFilterChainDecorator$ObservationFilter.doFilter(ObservationFilterChainDecorator.java:227) ~[spring-security-web-6.2.4.jar:6.2.4]
	at org.springframework.security.web.ObservationFilterChainDecorator$VirtualFilterChain.doFilter(ObservationFilterChainDecorator.java:137) ~[spring-security-web-6.2.4.jar:6.2.4]
	at org.springframework.security.oauth2.server.resource.web.authentication.BearerTokenAuthenticationFilter.doFilterInternal(BearerTokenAuthenticationFilter.java:145) ~[spring-security-oauth2-resource-server-6.2.4.jar:6.2.4]
	at org.springframework.web.filter.OncePerRequestFilter.doFilter(OncePerRequestFilter.java:116) ~[spring-web-6.1.6.jar:6.1.6]
	at org.springframework.security.web.ObservationFilterChainDecorator$ObservationFilter.wrapFilter(ObservationFilterChainDecorator.java:240) ~[spring-security-web-6.2.4.jar:6.2.4]
	at org.springframework.security.web.ObservationFilterChainDecorator$ObservationFilter.doFilter(ObservationFilterChainDecorator.java:227) ~[spring-security-web-6.2.4.jar:6.2.4]
	at org.springframework.security.web.ObservationFilterChainDecorator$VirtualFilterChain.doFilter(ObservationFilterChainDecorator.java:137) ~[spring-security-web-6.2.4.jar:6.2.4]
	at org.springframework.security.web.authentication.logout.LogoutFilter.doFilter(LogoutFilter.java:107) ~[spring-security-web-6.2.4.jar:6.2.4]
	at org.springframework.security.web.authentication.logout.LogoutFilter.doFilter(LogoutFilter.java:93) ~[spring-security-web-6.2.4.jar:6.2.4]
	at org.springframework.security.web.ObservationFilterChainDecorator$ObservationFilter.wrapFilter(ObservationFilterChainDecorator.java:240) ~[spring-security-web-6.2.4.jar:6.2.4]
	at org.springframework.security.web.ObservationFilterChainDecorator$ObservationFilter.doFilter(ObservationFilterChainDecorator.java:227) ~[spring-security-web-6.2.4.jar:6.2.4]
	at org.springframework.security.web.ObservationFilterChainDecorator$VirtualFilterChain.doFilter(ObservationFilterChainDecorator.java:137) ~[spring-security-web-6.2.4.jar:6.2.4]
	at org.springframework.web.filter.CorsFilter.doFilterInternal(CorsFilter.java:91) ~[spring-web-6.1.6.jar:6.1.6]
	at org.springframework.web.filter.OncePerRequestFilter.doFilter(OncePerRequestFilter.java:116) ~[spring-web-6.1.6.jar:6.1.6]
	at org.springframework.security.web.ObservationFilterChainDecorator$ObservationFilter.wrapFilter(ObservationFilterChainDecorator.java:240) ~[spring-security-web-6.2.4.jar:6.2.4]
	at org.springframework.security.web.ObservationFilterChainDecorator$ObservationFilter.doFilter(ObservationFilterChainDecorator.java:227) ~[spring-security-web-6.2.4.jar:6.2.4]
	at org.springframework.security.web.ObservationFilterChainDecorator$VirtualFilterChain.doFilter(ObservationFilterChainDecorator.java:137) ~[spring-security-web-6.2.4.jar:6.2.4]
	at org.springframework.security.web.header.HeaderWriterFilter.doHeadersAfter(HeaderWriterFilter.java:90) ~[spring-security-web-6.2.4.jar:6.2.4]
	at org.springframework.security.web.header.HeaderWriterFilter.doFilterInternal(HeaderWriterFilter.java:75) ~[spring-security-web-6.2.4.jar:6.2.4]
	at org.springframework.web.filter.OncePerRequestFilter.doFilter(OncePerRequestFilter.java:116) ~[spring-web-6.1.6.jar:6.1.6]
	at org.springframework.security.web.ObservationFilterChainDecorator$ObservationFilter.wrapFilter(ObservationFilterChainDecorator.java:240) ~[spring-security-web-6.2.4.jar:6.2.4]
	at org.springframework.security.web.ObservationFilterChainDecorator$ObservationFilter.doFilter(ObservationFilterChainDecorator.java:227) ~[spring-security-web-6.2.4.jar:6.2.4]
	at org.springframework.security.web.ObservationFilterChainDecorator$VirtualFilterChain.doFilter(ObservationFilterChainDecorator.java:137) ~[spring-security-web-6.2.4.jar:6.2.4]
	at org.springframework.security.web.context.SecurityContextHolderFilter.doFilter(SecurityContextHolderFilter.java:82) ~[spring-security-web-6.2.4.jar:6.2.4]
	at org.springframework.security.web.context.SecurityContextHolderFilter.doFilter(SecurityContextHolderFilter.java:69) ~[spring-security-web-6.2.4.jar:6.2.4]
	at org.springframework.security.web.ObservationFilterChainDecorator$ObservationFilter.wrapFilter(ObservationFilterChainDecorator.java:240) ~[spring-security-web-6.2.4.jar:6.2.4]
	at org.springframework.security.web.ObservationFilterChainDecorator$ObservationFilter.doFilter(ObservationFilterChainDecorator.java:227) ~[spring-security-web-6.2.4.jar:6.2.4]
	at org.springframework.security.web.ObservationFilterChainDecorator$VirtualFilterChain.doFilter(ObservationFilterChainDecorator.java:137) ~[spring-security-web-6.2.4.jar:6.2.4]
	at org.springframework.security.web.context.request.async.WebAsyncManagerIntegrationFilter.doFilterInternal(WebAsyncManagerIntegrationFilter.java:62) ~[spring-security-web-6.2.4.jar:6.2.4]
	at org.springframework.web.filter.OncePerRequestFilter.doFilter(OncePerRequestFilter.java:116) ~[spring-web-6.1.6.jar:6.1.6]
	at org.springframework.security.web.ObservationFilterChainDecorator$ObservationFilter.wrapFilter(ObservationFilterChainDecorator.java:240) ~[spring-security-web-6.2.4.jar:6.2.4]
	at org.springframework.security.web.ObservationFilterChainDecorator$ObservationFilter.doFilter(ObservationFilterChainDecorator.java:227) ~[spring-security-web-6.2.4.jar:6.2.4]
	at org.springframework.security.web.ObservationFilterChainDecorator$VirtualFilterChain.doFilter(ObservationFilterChainDecorator.java:137) ~[spring-security-web-6.2.4.jar:6.2.4]
	at org.springframework.security.web.session.DisableEncodeUrlFilter.doFilterInternal(DisableEncodeUrlFilter.java:42) ~[spring-security-web-6.2.4.jar:6.2.4]
	at org.springframework.web.filter.OncePerRequestFilter.doFilter(OncePerRequestFilter.java:116) ~[spring-web-6.1.6.jar:6.1.6]
	at org.springframework.security.web.ObservationFilterChainDecorator$ObservationFilter.wrapFilter(ObservationFilterChainDecorator.java:240) ~[spring-security-web-6.2.4.jar:6.2.4]
	at org.springframework.security.web.ObservationFilterChainDecorator$AroundFilterObservation$SimpleAroundFilterObservation.lambda$wrap$0(ObservationFilterChainDecorator.java:323) ~[spring-security-web-6.2.4.jar:6.2.4]
	at org.springframework.security.web.ObservationFilterChainDecorator$ObservationFilter.doFilter(ObservationFilterChainDecorator.java:224) ~[spring-security-web-6.2.4.jar:6.2.4]
	at org.springframework.security.web.ObservationFilterChainDecorator$VirtualFilterChain.doFilter(ObservationFilterChainDecorator.java:137) ~[spring-security-web-6.2.4.jar:6.2.4]
	at org.springframework.security.web.FilterChainProxy.doFilterInternal(FilterChainProxy.java:233) ~[spring-security-web-6.2.4.jar:6.2.4]
	at org.springframework.security.web.FilterChainProxy.doFilter(FilterChainProxy.java:191) ~[spring-security-web-6.2.4.jar:6.2.4]
	at org.springframework.web.filter.CompositeFilter$VirtualFilterChain.doFilter(CompositeFilter.java:113) ~[spring-web-6.1.6.jar:6.1.6]
	at org.springframework.web.servlet.handler.HandlerMappingIntrospector.lambda$createCacheFilter$3(HandlerMappingIntrospector.java:195) ~[spring-webmvc-6.1.6.jar:6.1.6]
	at org.springframework.web.filter.CompositeFilter$VirtualFilterChain.doFilter(CompositeFilter.java:113) ~[spring-web-6.1.6.jar:6.1.6]
	at org.springframework.web.filter.CompositeFilter.doFilter(CompositeFilter.java:74) ~[spring-web-6.1.6.jar:6.1.6]
	at org.springframework.security.config.annotation.web.configuration.WebMvcSecurityConfiguration$CompositeFilterChainProxy.doFilter(WebMvcSecurityConfiguration.java:230) ~[spring-security-config-6.2.4.jar:6.2.4]
	at org.springframework.web.filter.DelegatingFilterProxy.invokeDelegate(DelegatingFilterProxy.java:352) ~[spring-web-6.1.6.jar:6.1.6]
	at org.springframework.web.filter.DelegatingFilterProxy.doFilter(DelegatingFilterProxy.java:268) ~[spring-web-6.1.6.jar:6.1.6]
	at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:175) ~[tomcat-embed-core-10.1.20.jar:10.1.20]
	at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:150) ~[tomcat-embed-core-10.1.20.jar:10.1.20]
	at org.springframework.web.filter.RequestContextFilter.doFilterInternal(RequestContextFilter.java:100) ~[spring-web-6.1.6.jar:6.1.6]
	at org.springframework.web.filter.OncePerRequestFilter.doFilter(OncePerRequestFilter.java:116) ~[spring-web-6.1.6.jar:6.1.6]
	at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:175) ~[tomcat-embed-core-10.1.20.jar:10.1.20]
	at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:150) ~[tomcat-embed-core-10.1.20.jar:10.1.20]
	at org.springframework.web.filter.FormContentFilter.doFilterInternal(FormContentFilter.java:93) ~[spring-web-6.1.6.jar:6.1.6]
	at org.springframework.web.filter.OncePerRequestFilter.doFilter(OncePerRequestFilter.java:116) ~[spring-web-6.1.6.jar:6.1.6]
	at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:175) ~[tomcat-embed-core-10.1.20.jar:10.1.20]
	at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:150) ~[tomcat-embed-core-10.1.20.jar:10.1.20]
	at org.springframework.web.filter.ServerHttpObservationFilter.doFilterInternal(ServerHttpObservationFilter.java:109) ~[spring-web-6.1.6.jar:6.1.6]
	at org.springframework.web.filter.OncePerRequestFilter.doFilter(OncePerRequestFilter.java:116) ~[spring-web-6.1.6.jar:6.1.6]
	at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:175) ~[tomcat-embed-core-10.1.20.jar:10.1.20]
	at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:150) ~[tomcat-embed-core-10.1.20.jar:10.1.20]
	at org.springframework.web.filter.CharacterEncodingFilter.doFilterInternal(CharacterEncodingFilter.java:201) ~[spring-web-6.1.6.jar:6.1.6]
	at org.springframework.web.filter.OncePerRequestFilter.doFilter(OncePerRequestFilter.java:116) ~[spring-web-6.1.6.jar:6.1.6]
	at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:175) ~[tomcat-embed-core-10.1.20.jar:10.1.20]
	at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:150) ~[tomcat-embed-core-10.1.20.jar:10.1.20]
	at com.ford.cybersecurity.lookupportal.logging.LoggingFilter.doFilterInternal(LoggingFilter.kt:29) ~[classes/:na]
	at org.springframework.web.filter.OncePerRequestFilter.doFilter(OncePerRequestFilter.java:116) ~[spring-web-6.1.6.jar:6.1.6]
	at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:175) ~[tomcat-embed-core-10.1.20.jar:10.1.20]
	at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:150) ~[tomcat-embed-core-10.1.20.jar:10.1.20]
	at org.apache.catalina.core.StandardWrapperValve.invoke(StandardWrapperValve.java:167) ~[tomcat-embed-core-10.1.20.jar:10.1.20]
	at org.apache.catalina.core.StandardContextValve.invoke(StandardContextValve.java:90) ~[tomcat-embed-core-10.1.20.jar:10.1.20]
	at org.apache.catalina.authenticator.AuthenticatorBase.invoke(AuthenticatorBase.java:482) ~[tomcat-embed-core-10.1.20.jar:10.1.20]
	at org.apache.catalina.core.StandardHostValve.invoke(StandardHostValve.java:115) ~[tomcat-embed-core-10.1.20.jar:10.1.20]
	at org.apache.catalina.valves.ErrorReportValve.invoke(ErrorReportValve.java:93) ~[tomcat-embed-core-10.1.20.jar:10.1.20]
	at org.apache.catalina.core.StandardEngineValve.invoke(StandardEngineValve.java:74) ~[tomcat-embed-core-10.1.20.jar:10.1.20]
	at org.apache.catalina.connector.CoyoteAdapter.service(CoyoteAdapter.java:344) ~[tomcat-embed-core-10.1.20.jar:10.1.20]
	at org.apache.coyote.http11.Http11Processor.service(Http11Processor.java:391) ~[tomcat-embed-core-10.1.20.jar:10.1.20]
	at org.apache.coyote.AbstractProcessorLight.process(AbstractProcessorLight.java:63) ~[tomcat-embed-core-10.1.20.jar:10.1.20]
	at org.apache.coyote.AbstractProtocol$ConnectionHandler.process(AbstractProtocol.java:896) ~[tomcat-embed-core-10.1.20.jar:10.1.20]
	at org.apache.tomcat.util.net.NioEndpoint$SocketProcessor.doRun(NioEndpoint.java:1736) ~[tomcat-embed-core-10.1.20.jar:10.1.20]
	at org.apache.tomcat.util.net.SocketProcessorBase.run(SocketProcessorBase.java:52) ~[tomcat-embed-core-10.1.20.jar:10.1.20]
	at org.apache.tomcat.util.threads.ThreadPoolExecutor.runWorker(ThreadPoolExecutor.java:1191) ~[tomcat-embed-core-10.1.20.jar:10.1.20]
	at org.apache.tomcat.util.threads.ThreadPoolExecutor$Worker.run(ThreadPoolExecutor.java:659) ~[tomcat-embed-core-10.1.20.jar:10.1.20]
	at org.apache.tomcat.util.threads.TaskThread$WrappingRunnable.run(TaskThread.java:63) ~[tomcat-embed-core-10.1.20.jar:10.1.20]
	at java.base/java.lang.Thread.run(Unknown Source) ~[na:na]"

Application specification

Java 17

Related libraries:

org.springframework.boot gradle plugin, version 3.2.5
io.spring.dependency-management gradle plugin, version 1.1.5
org.springframework.boot:spring-boot-starter-mail dependency, version 3.2.5
com.icegreen:greenmail test dependency, version 2.1.2

Spring Boot properties:

spring.mail.host=<my-mail-host>
spring.mail.username=<my-mail-username>
spring.mail.password=<my-mail-password>
spring.mail.port=25
spring.mail.properties.mail.smtp.auth=true
spring.mail.properties.mail.smtp.starttls.enable=true
spring.mail.properties.mail.smtp.debug=true
spring.mail.properties.mail.transport.protocol=smtp

Beans:

I have a configuration for JavaMailSender beans:

@Configuration
class EmailConfiguration {

    @Bean
    @Profile("!qa & !prod & !email-test")
    fun localMailSender(): JavaMailSender {
        return JavaMailSenderImpl()
    }

    @Bean
    @Profile("email-test")
    fun testMailSender(): JavaMailSender {
        val testMailSender = JavaMailSenderImpl()
        testMailSender.host = "localhost"
        testMailSender.port = 3025
        return testMailSender
    }

}

email-test profile is used with greenmail in some mail related Spring Boot Test, and default profile is used in other Spring Boot Test. prod and qa are cloud profiles that should configure JavaMailSender from Spring Boot properties.

The behavior was intermittent because from time to time it was able to send mail. I read about the error online, and the remediation I found working was to set another mail property to the mail host:

spring.mail.properties.mail.smtp.localhost=${spring.mail.host}

I would like to know what caused this sudden change of intermittent error behavior. Please let me know if you need me to provide more information.
@spring-projects-issues spring-projects-issues added the status: waiting-for-triage An issue we've not yet triaged label Mar 7, 2025
@yangzii0920 yangzii0920 changed the title Spring Mail intermittent error from HELO/EHLO spring-mail 3.2.5 intermittent error from HELO/EHLO Mar 7, 2025
@wilkinsona
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Spring Boot 3.2.x is no longer supported. Please upgrade to a supported version (3.3.x or later). If the problem remains, please provide a complete yet minimal sample that reproduces the problem.

@wilkinsona wilkinsona added the status: waiting-for-feedback We need additional information before we can continue label Mar 7, 2025
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If you would like us to look at this issue, please provide the requested information. If the information is not provided within the next 7 days this issue will be closed.

@spring-projects-issues spring-projects-issues added the status: feedback-reminder We've sent a reminder that we need additional information before we can continue label Mar 14, 2025
@yangzii0920
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Thank you for following up on this! I'm working on upgrading the application to Spring Boot 3.4 but it's taking longer than I expected with all the dependencies. I'll try to reproduce the issue with Spring Boot 3.4, but since the issue seemed to be intermittent and specific to one of deployment environment, I understand if this has to be closed for now in 7 days.

@spring-projects-issues spring-projects-issues added status: feedback-provided Feedback has been provided and removed status: waiting-for-feedback We need additional information before we can continue status: feedback-reminder We've sent a reminder that we need additional information before we can continue labels Mar 14, 2025
@wilkinsona wilkinsona added status: waiting-for-feedback We need additional information before we can continue status: feedback-reminder We've sent a reminder that we need additional information before we can continue and removed status: feedback-provided Feedback has been provided labels Mar 14, 2025
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Closing due to lack of requested feedback. If you would like us to look at this issue, please provide the requested information and we will re-open the issue.

@spring-projects-issues spring-projects-issues closed this as not planned Won't fix, can't repro, duplicate, stale Mar 28, 2025
@spring-projects-issues spring-projects-issues removed status: waiting-for-feedback We need additional information before we can continue status: feedback-reminder We've sent a reminder that we need additional information before we can continue status: waiting-for-triage An issue we've not yet triaged labels Mar 28, 2025
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