# Invalid email addresses error? **URL:** \ **Category:** Ignition\ **Tags:** ignition80\ **Created:** [April 5, 2022, 1:57pm UTC](https://forum.inductiveautomation.com/t/invalid-email-addresses-error/58047 "2022-04-05T13:57:12Z")\ **Posts on this page:** 9\ **Page:** 1
**Author:** ![bkarabinchak.psi](https://sea1.discourse-cdn.com/inductiveautomation/user_avatar/forum.inductiveautomation.com/bkarabinchak.psi/32/83567_2.png) [@bkarabinchak.psi](https://forum.inductiveautomation.com/u/bkarabinchak.psi)\ **Post date:** [April 5, 2022, 1:57pm UTC](https://forum.inductiveautomation.com/t/invalid-email-addresses-error/58047/1 "2022-04-05T13:57:12Z")
Part of my application is emailing out invoices. Today and yesterday apparently the emails have been not sending. I see the following in my logs ```auto javax.mail.SendFailedException: Invalid Addresses at com.sun.mail.smtp.SMTPTransport.rcptTo(SMTPTransport.java:1949) at com.sun.mail.smtp.SMTPTransport.sendMessage(SMTPTransport.java:1195) at javax.mail.Transport.send0(Transport.java:254) at javax.mail.Transport.send(Transport.java:124) at com.inductiveautomation.ignition.gateway.smtp.SmtpManagerImpl.sendMailWithRetries(SmtpManagerImpl.java:239) at com.inductiveautomation.ignition.gateway.smtp.SmtpManagerImpl.sendEmail(SmtpManagerImpl.java:206) at com.inductiveautomation.ignition.gateway.servlets.Gateway.sendEmail(Gateway.java:1221) at com.inductiveautomation.ignition.gateway.servlets.Gateway.doPost(Gateway.java:478) at javax.servlet.http.HttpServlet.service(HttpServlet.java:707) at javax.servlet.http.HttpServlet.service(HttpServlet.java:790) at com.inductiveautomation.ignition.gateway.bootstrap.MapServlet.service(MapServlet.java:86) at org.eclipse.jetty.servlet.ServletHolder$NotAsyncServlet.service(ServletHolder.java:1391) at org.eclipse.jetty.servlet.ServletHolder.handle(ServletHolder.java:760) at org.eclipse.jetty.servlet.ServletHandler.doHandle(ServletHandler.java:547) at org.eclipse.jetty.server.handler.ScopedHandler.handle(ScopedHandler.java:143) at org.eclipse.jetty.security.SecurityHandler.handle(SecurityHandler.java:590) at org.eclipse.jetty.server.handler.HandlerWrapper.handle(HandlerWrapper.java:127) at org.eclipse.jetty.server.handler.ScopedHandler.nextHandle(ScopedHandler.java:235) at org.eclipse.jetty.server.session.SessionHandler.doHandle(SessionHandler.java:1607) at org.eclipse.jetty.server.handler.ScopedHandler.nextHandle(ScopedHandler.java:233) at org.eclipse.jetty.server.handler.ContextHandler.doHandle(ContextHandler.java:1297) at org.eclipse.jetty.server.handler.ScopedHandler.nextScope(ScopedHandler.java:188) at org.eclipse.jetty.servlet.ServletHandler.doScope(ServletHandler.java:485) at org.eclipse.jetty.server.session.SessionHandler.doScope(SessionHandler.java:1577) at org.eclipse.jetty.server.handler.ScopedHandler.nextScope(ScopedHandler.java:186) at org.eclipse.jetty.server.handler.ContextHandler.doScope(ContextHandler.java:1212) at org.eclipse.jetty.server.handler.ScopedHandler.handle(ScopedHandler.java:141) at org.eclipse.jetty.server.handler.HandlerList.handle(HandlerList.java:59) at org.eclipse.jetty.server.handler.HandlerWrapper.handle(HandlerWrapper.java:127) at org.eclipse.jetty.rewrite.handler.RewriteHandler.handle(RewriteHandler.java:322) at org.eclipse.jetty.server.handler.HandlerList.handle(HandlerList.java:59) at org.eclipse.jetty.server.handler.HandlerCollection.handle(HandlerCollection.java:146) at org.eclipse.jetty.server.handler.HandlerWrapper.handle(HandlerWrapper.java:127) at org.eclipse.jetty.server.Server.handle(Server.java:500) at org.eclipse.jetty.server.HttpChannel.lambda$handle$1(HttpChannel.java:383) at org.eclipse.jetty.server.HttpChannel.dispatch(HttpChannel.java:547) at org.eclipse.jetty.server.HttpChannel.handle(HttpChannel.java:375) at org.eclipse.jetty.server.HttpConnection.onFillable(HttpConnection.java:270) at org.eclipse.jetty.io.AbstractConnection$ReadCallback.succeeded(AbstractConnection.java:311) at org.eclipse.jetty.io.FillInterest.fillable(FillInterest.java:103) at org.eclipse.jetty.io.ChannelEndPoint$2.run(ChannelEndPoint.java:117) at org.eclipse.jetty.util.thread.strategy.EatWhatYouKill.runTask(EatWhatYouKill.java:336) at org.eclipse.jetty.util.thread.strategy.EatWhatYouKill.doProduce(EatWhatYouKill.java:313) at org.eclipse.jetty.util.thread.strategy.EatWhatYouKill.tryProduce(EatWhatYouKill.java:171) at org.eclipse.jetty.util.thread.strategy.EatWhatYouKill.run(EatWhatYouKill.java:129) at org.eclipse.jetty.util.thread.ReservedThreadExecutor$ReservedThread.run(ReservedThreadExecutor.java:388) at org.eclipse.jetty.util.thread.QueuedThreadPool.runJob(QueuedThreadPool.java:806) at org.eclipse.jetty.util.thread.QueuedThreadPool$Runner.run(QueuedThreadPool.java:938) at java.base/java.lang.Thread.run(Unknown Source) Caused by: com.sun.mail.smtp.SMTPAddressFailedException: 452 4.5.3 Too many recipients ATTR48 [MW2NAM12FT038.eop-nam12.prod.protection.outlook.com] at com.sun.mail.smtp.SMTPTransport.rcptTo(SMTPTransport.java:1816) ... 48 common frames omitted Caused by: com.sun.mail.smtp.SMTPAddressFailedException: 452 4.5.3 Too many recipients ATTR48 [MW2NAM12FT038.eop-nam12.prod.protection.outlook.com] ``` And beneath that two logs leading up to it - first one ```auto Trying to send email 'Invoice #5100-2022-1-6, Computer Support - 2021-10-29 thru 2022-03-13 plus hardware' to [someone@someCompany.com, ealter@primarysys.com, kcampo@primarysys.com] failed. Please correct the problem and try again. ``` Followed by ```auto Sending email Invoice #5100-2022-1-6, Computer Support - 2021-10-29 thru 2022-03-13 plus hardware to address(es) [someone@someCompany.com, ealter@primarysys.com, kcampo@primarysys.com] failed. Will retry 0 more time(s). ``` I know all three of those email addresses are valid - ealter and kcampo are emails within my company (for which I have credentials in the gateway, not that should matter - but ealter is the sender here). And [someone@someCompany.com](mailto:someone@someCompany.com), changed for privacy, I emailed them directly just last week (through outlook, not through Ignition). So I am at a loss as to what is causing these errors - the past two days no emails have gone out (not just for [someone@someCompany.com](mailto:someone@someCompany.com), but other customer emails known to be valid from direct communications via outlook and not Ignition based). Any ideas as to what is going wrong? ---
**Author:** ![lrose](https://sea1.discourse-cdn.com/inductiveautomation/user_avatar/forum.inductiveautomation.com/lrose/32/62724_2.png) [@lrose](https://forum.inductiveautomation.com/u/lrose)\ **Post date:** [April 5, 2022, 2:07pm UTC](https://forum.inductiveautomation.com/t/invalid-email-addresses-error/58047/2 "2022-04-05T14:07:52Z")
Are there only the 3 recipients on the message? Seems odd to be getting: ```auto Caused by: com.sun.mail.smtp.SMTPAddressFailedException: 452 4.5.3 Too many recipients ATTR48 [MW2NAM12FT038.eop-nam12.prod.protection.outlook.com] ``` For only 3 addresses. ---
**Author:** ![pturmel](https://sea1.discourse-cdn.com/inductiveautomation/user_avatar/forum.inductiveautomation.com/pturmel/32/3295_2.png) [@pturmel](https://forum.inductiveautomation.com/u/pturmel)\ **Post date:** [April 5, 2022, 2:08pm UTC](https://forum.inductiveautomation.com/t/invalid-email-addresses-error/58047/3 "2022-04-05T14:08:02Z")
Without seeing the actual TO address, it is hard to tell. But the RFC for email addresses is pretty strict, and not tolerant of international characters. Most email clients will encode otherwise non-compliant addresses automatically. Use “view source” on one of those emails to see the “real” address. I bet it is encoded. ---
**Author:** ![bkarabinchak.psi](https://sea1.discourse-cdn.com/inductiveautomation/user_avatar/forum.inductiveautomation.com/bkarabinchak.psi/32/83567_2.png) [@bkarabinchak.psi](https://forum.inductiveautomation.com/u/bkarabinchak.psi)\ **Post date:** [April 5, 2022, 2:08pm UTC](https://forum.inductiveautomation.com/t/invalid-email-addresses-error/58047/4 "2022-04-05T14:08:49Z")
Yes only three addresses, a customer, and then two employees here get a copy. ---
**Author:** ![paul-griffith](https://sea1.discourse-cdn.com/inductiveautomation/user_avatar/forum.inductiveautomation.com/paul-griffith/32/37249_2.png) [@paul-griffith](https://forum.inductiveautomation.com/u/paul-griffith)\ **Post date:** [April 5, 2022, 2:17pm UTC](https://forum.inductiveautomation.com/t/invalid-email-addresses-error/58047/5 "2022-04-05T14:17:11Z")
To @lrose’ point : maybe your SMTP server doesn’t “like” sending an outbound mail (from Ignition) to someone outside of your domain now, due to an IT restriction? ---
**Author:** ![bkarabinchak.psi](https://sea1.discourse-cdn.com/inductiveautomation/user_avatar/forum.inductiveautomation.com/bkarabinchak.psi/32/83567_2.png) [@bkarabinchak.psi](https://forum.inductiveautomation.com/u/bkarabinchak.psi)\ **Post date:** [April 5, 2022, 2:23pm UTC](https://forum.inductiveautomation.com/t/invalid-email-addresses-error/58047/6 "2022-04-05T14:23:32Z")
Yea apparently IT did change something recently. Talking with them now. Seems to be something on the Outlook side of things. It thinks things are spam when they are not. Will post an answer when it’s figured out. ---
**Author:** ![lrose](https://sea1.discourse-cdn.com/inductiveautomation/user_avatar/forum.inductiveautomation.com/lrose/32/62724_2.png) [@lrose](https://forum.inductiveautomation.com/u/lrose)\ **Post date:** [April 5, 2022, 3:21pm UTC](https://forum.inductiveautomation.com/t/invalid-email-addresses-error/58047/7 "2022-04-05T15:21:33Z")
Perhaps this will help? > **[Error: 452 4.5.3 Too many recipients](https://bqekb.zendesk.com/hc/en-us/articles/360042951692-Error-452-4-5-3-Too-many-recipients)** > > When emailing invoices to the clients from ArchiOffice (or EngineerOffice), the users sometimes get the following error message from the recipient email servers: > Error: 452 4.5.3 Too many recipient... ---
**Author:** ![bkarabinchak.psi](https://sea1.discourse-cdn.com/inductiveautomation/user_avatar/forum.inductiveautomation.com/bkarabinchak.psi/32/83567_2.png) [@bkarabinchak.psi](https://forum.inductiveautomation.com/u/bkarabinchak.psi)\ **Post date:** [April 5, 2022, 4:50pm UTC](https://forum.inductiveautomation.com/t/invalid-email-addresses-error/58047/8 "2022-04-05T16:50:13Z")
I tested sending emails out directly from the gateway page and within our company domain it worked but going out to any other domain, even something like gmail, was throwing a Relay Access Denied Error. Found this related to it > **[550 5.7.64 TenantAttribution; Relay Access Denied SMTP when users send mails...](https://docs.microsoft.com/en-us/exchange/troubleshoot/email-delivery/relay-access-denied-smtp)** > > 550 5.7.64 TenantAttribution; Relay Access Denied SMTP bounce backs for external emails being relayed out through Office 365. IT took care of it so I can’t give list out the exact trouble shooting steps they took. However, to any future viewers of this post, I would recommend doing some email testing from within your gateway page and check - does outgoing work for other people in your domain? Does it work for people on a different domain? And go from there. ---
**Author:** ![josborn](https://avatars.discourse-cdn.com/v4/letter/j/4bbf92/32.png) [@josborn](https://forum.inductiveautomation.com/u/josborn)\ **Post date:** [April 5, 2022, 5:10pm UTC](https://forum.inductiveautomation.com/t/invalid-email-addresses-error/58047/9 "2022-04-05T17:10:26Z")
You really are at IT’s mercy in this kind of situation. As an example, i had a long standing issue where some emails would randomly just not be delivered. No error, they just went into the void. Turns out they imposed a limit on how many emails could go out per an arbitrary time interval.