Using smtp.gmail.com for sending mail issues?

For our community we use smtp.gmail.com as the smtp server.  It mostly works but periodically authentication with the SMTP Login Name & Password begins failing and the Verint exception log fills up with EmailUnabletoSend errors.  To fix it, I re-add the SMTP Login Name & Password to the Site - Email Options page and everything begins flowing again.  Is this a common occurrence with smtp.gmail.com?  Is there a better way to mitigate it other than watching for EmailUnabletoSend errors?

Thanks

Bill

Parents
  • Still trying to fix this annoyance with SMTP.  Here's the relevant bits from the exception log:

    UnknownException: Email failed to send (To: jmccarthy@tracelink.com) (Subject: You've been approved! Here's how to activate your profile, JeffreyMcCarthy) Message log: { 19:05:38.910 }---- aspNetEmail 3.7.0.10 [Wednesday, September 21, 2022] -----
    { 19:05:38.910 }.NET Version [4.0.30319.42000]
    { 19:05:38.910 }Opening mail server connection.
    { 19:05:38.910 }Checking for PopBeforeSmtp.
    { 19:05:38.910 }Attempting connection to smtp.gmail.com.
    { 19:05:38.910 }Connecting to mail server [smtp.gmail.com] .
    { 19:05:38.910 }SSL Object Version: 2.0.0.5
    { 19:05:38.910 }Server [smtp.gmail.com] is not an IP address. Performing DNS resolution.
    { 19:05:38.911 }Server [smtp.gmail.com] resolved to IP address 172.253.63.109
    { 19:05:38.913 }Connected to smtp.gmail.com with a timeout of 60000ms.
    { 19:05:38.913 }Remote port: 587
    { 19:05:38.945 }220 smtp.gmail.com ESMTP n18-20020a05622a041200b0035a71a41645sm2326226qtx.37 - gsmtp
    { 19:05:38.945 }EHLO EC2AMAZ-PLDU4IJ
    { 19:05:38.956 }250-smtp.gmail.com at your service, [18.215.19.74]
    250-SIZE 35882577
    250-8BITMIME
    250-STARTTLS
    250-ENHANCEDSTATUSCODES
    250-PIPELINING
    250-CHUNKING
    250 SMTPUTF8
    { 19:05:38.956 }Server does not support the DSN extension.  The DeliveryNotification property will be ignored.
    { 19:05:38.956 }STARTTLS
    { 19:05:38.965 }220 2.0.0 Ready to start TLS
    { 19:05:38.965 }Starting TLS session.
    { 19:05:38.968 }TLS session started.
    { 19:05:38.968 }EHLO EC2AMAZ-PLDU4IJ
    { 19:05:38.984 }250-smtp.gmail.com at your service, [18.215.19.74]
    250-SIZE 35882577
    250-8BITMIME
    250-AUTH LOGIN PLAIN XOAUTH2 PLAIN-CLIENTTOKEN OAUTHBEARER XOAUTH
    250-ENHANCEDSTATUSCODES
    250-PIPELINING
    250-CHUNKING
    250 SMTPUTF8
    { 19:05:38.984 }Server does not support the DSN extension.  The DeliveryNotification property will be ignored.
    { 19:05:38.984 }AUTH LOGIN
    { 19:05:38.993 }334 VXNlcm5hbWU6
    { 19:05:38.993 }YWRtaW5AZ2VvcmdpYW5ncm93dGhuZXR3b3JrLmlv
    { 19:05:39.001 }334 UGFzc3dvcmQ6
    { 19:05:39.001 }UEtCN1pkS0F5dXo4LUpAcl9ARm1qKjMt
    { 19:05:39.012 }454 4.7.0 Too many login attempts, please try again later. n18-20020a05622a041200b0035a71a41645sm2326226qtx.37 - gsmtp
    { 19:05:39.012 } [Additional Help:Authentication failed. Check your username and/or password.454 4.7.0 Too many login attempts, please try again later. n18-20020a05622a041200b0035a71a41645sm2326226qtx.37 - gsmtp
    ]
    { 19:05:39.012 } [Additional Help:Authentication failed. Check your username and/or password.454 4.7.0 Too many login attempts, please try again later. n18-20020a05622a041200b0035a71a41645sm2326226qtx.37 - gsmtp
    ]
     (We apologize, but an error occurred while attempting to send email.) ---> aspNetEmail.SmtpProtocolException:  [Additional Help:Authentication failed. Check your username and/or password.454 4.7.0 Too many login attempts, please try again later. n18-20020a05622a041200b0035a71a41645sm2326226qtx.37 - gsmtp
    ]
       at aspNetEmail.EmailMessage.ᑌ(String , Exception )
       at aspNetEmail.EmailMessage.Send(Boolean openMailServerConnection, Boolean closeMailServerConnection)
       at Telligent.Evolution.Platform.Core.Email.SendEmailService.InternalSend(EmailMessage message)
       --- End of inner exception stack trace ---
       at Telligent.Evolution.Platform.Core.Email.SendEmailService.InternalSend(EmailMessage message)
       at Telligent.Evolution.Platform.Core.Email.SendEmailService.SendMessage(String messageText, Int32 numTries)
       at Telligent.Evolution.Extensibility.Api.Version1.SendEmail.Execute(JobData jobData)
       at Telligent.Evolution.Components.Jobs.DynamicEvolutionJobRunner.SubExecute(JobExecutionContext context)
       at Telligent.Evolution.Components.Jobs.BaseJobRunner.Execute(JobExecutionContext job)
       at Telligent.Jobs.JobConsumer.<>c__DisplayClass20_0.<Consume>b__0()
       at System.Threading.Tasks.Task.InnerInvoke()
       at System.Threading.Tasks.Task.Execute()
       at System.Threading.Tasks.Task.ExecutionContextCallback(Object obj)
       at System.Threading.ExecutionContext.RunInternal(ExecutionContext executionContext, ContextCallback callback, Object state, Boolean preserveSyncCtx)
       at System.Threading.ExecutionContext.Run(ExecutionContext executionContext, ContextCallback callback, Object state, Boolean preserveSyncCtx)
       at System.Threading.Tasks.Task.ExecuteWithThreadLocal(Task& currentTaskSlot)
       at System.Threading.Tasks.Task.ExecuteEntry(Boolean bPreventDoubleExecution)
       at System.Threading.Tasks.Task.System.Threading.IThreadPoolWorkItem.ExecuteWorkItem()
       at System.Threading.ThreadPoolWorkQueue.Dispatch()
       at System.Threading._ThreadPoolWaitCallback.PerformWaitCallback()

    The Verint platform continues to try to send the mail and eventually it works correctly. But my logs are full of Unable to Send email messages even though the mail eventually gets sent. Is there anything about the way that the Verint send mail function operates that would be preventing immediate authentication with the Google Gmail smtp service?
    Has anyone else complained about this who's using Google's smtp service?

    Thanks
    Bill



    fixed formatting
    [edited by: Bill Traynor at 7:18 PM (GMT 0) on Wed, Sep 21 2022]
  • In this situation, did the username/password actually change? This error "Too many login attempts, please try again later." based on Gmail support online suggests that the authentication failed and Gmail is temporarily blocking login attempts (either from that IP or for that account -- it is not clear).

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