Workflow and alerts not being sent SPMailMessageHelper.SendMailMessage : Server does not support secure connections

Question

_{Tuesday, July 23, 2019 8:34 PM}

I have a new SharePoint 2019 environment. Alerts and emails generated from Workflow Manager are not being sent. For outgoing mail settings on Central Admin I have my Outbound SMTP server identified, SMTP server authentication is set to Anonymous and Use TLS connection is set to No. I have the same settings on our SharePoint 2016 environment and emails are being generated. Below is info on the logs. any help is appreciated.

SPMailMessageHelper.SendMailMessage Failure: System.Net.Mail.SmtpException: Server does not support secure connections. at System.Net.Mail.SmtpConnection.GetConnection(ServicePoint servicePoint) at System.Net.Mail.SmtpClient.GetConnection() at System.Net.Mail.SmtpClient.Send(MailMessage message) at Microsoft.SharePoint.Email.SPSmtpClient.SendOnce(MailMessage msg, Boolean useAlternateServer) at Microsoft.SharePoint.Email.SPSmtpClient.Send(MailMessage msg) at Microsoft.SharePoint.Email.SPMailMessageHelper.SendMailMessage(SPSmtpClient smtpClient, MailMessage mailMessage, Boolean useEws)

Exception occured in scope Microsoft.SharePoint.Utilities.SPUtility.SendEmail. Exception=System.Net.Mail.SmtpException: Server does not support secure connections. at System.Net.Mail.SmtpConnection.GetConnection(ServicePoint servicePoint) at System.Net.Mail.SmtpClient.GetConnection() at System.Net.Mail.SmtpClient.Send(MailMessage message) at Microsoft.SharePoint.Email.SPSmtpClient.SendOnce(MailMessage msg, Boolean useAlternateServer) at Microsoft.SharePoint.Email.SPSmtpClient.Send(MailMessage msg) at Microsoft.SharePoint.Email.SPMailMessageHelper.SendMailMessage(SPSmtpClient smtpClient, MailMessage mailMessage, Boolean useEws) at Microsoft.SharePoint.Email.SPMailMessageHelper.SendMailMessage(SPSite site, MailMessage mailMessage, Boolean useEws) at Microsoft.SharePoint.Utilities.SPUtility.SendEmail_ClientInternal(SPWeb web, EmailProperties properties, FromAddressGenerator generateFromFunc) at Microsoft.SharePoint.ServerStub.Utilities.SPUtilityServerStub.InvokeStaticMethod(String methodName, ClientValueCollection xmlargs, ProxyContext proxyContext, Boolean& isVoid) at Microsoft.SharePoint.Client.ServerStub.InvokeStaticMethodWithMonitoredScope(String methodName, ClientValueCollection args, ProxyContext proxyContext, Boolean& isVoid)

Original error: System.Net.Mail.SmtpException: Server does not support secure connections. at System.Net.Mail.SmtpConnection.GetConnection(ServicePoint servicePoint) at System.Net.Mail.SmtpClient.GetConnection() at System.Net.Mail.SmtpClient.Send(MailMessage message) at Microsoft.SharePoint.Email.SPSmtpClient.SendOnce(MailMessage msg, Boolean useAlternateServer) at Microsoft.SharePoint.Email.SPSmtpClient.Send(MailMessage msg) at Microsoft.SharePoint.Email.SPMailMessageHelper.SendMailMessage(SPSmtpClient smtpClient, MailMessage mailMessage, Boolean useEws) at Microsoft.SharePoint.Email.SPMailMessageHelper.SendMailMessage(SPSite site, MailMessage mailMessage, Boolean useEws) at Microsoft.SharePoint.Utilities.SPUtility.SendEmail_ClientInternal(SPWeb web, EmailProperties properties, FromAddressGenerator generateFromFunc) at Microsoft.SharePoint.ServerStub.Utilities.SPUtilityServerStub.InvokeStaticMethod(String methodName, ClientValueCollection xmlargs, ProxyContext proxyContext, Boolean& isVoid) at Microsoft.SharePoint.Client.ServerStub.InvokeStaticMethodWithMonitoredScope(String methodName, ClientValueCollection args, ProxyContext proxyContext, Boolean& isVoid)

SocialRESTExceptionProcessingHandler.DoServerExceptionProcessing - SharePoint Server Exception [System.Net.Mail.SmtpException: Server does not support secure connections. at System.Net.Mail.SmtpConnection.GetConnection(ServicePoint servicePoint) at System.Net.Mail.SmtpClient.GetConnection() at System.Net.Mail.SmtpClient.Send(MailMessage message) at Microsoft.SharePoint.Email.SPSmtpClient.SendOnce(MailMessage msg, Boolean useAlternateServer) at Microsoft.SharePoint.Email.SPSmtpClient.Send(MailMessage msg) at Microsoft.SharePoint.Email.SPMailMessageHelper.SendMailMessage(SPSmtpClient smtpClient, MailMessage mailMessage, Boolean useEws) at Microsoft.SharePoint.Email.SPMailMessageHelper.SendMailMessage(SPSite site, MailMessage mailMessage, Boolean useEws) at Microsoft.SharePoint.Utilities.SPUtility.SendEmail_ClientInternal(SPWeb web, EmailProperties properties, FromAddressGenerator generateFromFunc) at Microsoft.SharePoint.ServerStub.Utilities.SPUtilityServerStub.InvokeStaticMethod(String methodName, ClientValueCollection xmlargs, ProxyContext proxyContext, Boolean& isVoid) at Microsoft.SharePoint.Client.ServerStub.InvokeStaticMethodWithMonitoredScope(String methodName, ClientValueCollection args, ProxyContext proxyContext, Boolean& isVoid)]

Evy

All replies (5)

_{Wednesday, July 24, 2019 9:55 AM}

Hi Evy,

Go to Manage web application-> select a web application-> General Settings group on the ribbon->click Outgoing E-mail, check if the outgoing email settings are configured correctly for certain web application.

Since SMTP protocol typically uses ports 587 and 25 for non SSL connections, make sure the outbound SMTP server port is 25 or 587 when you configure outgoing email settings.

If the issue still exists, try to create an additional receive connector on Exchange server, set to allow connections from the SP server IP address, with only Anonymous authentication enabled.

Best regards,

Grace Wang

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_{Wednesday, July 24, 2019 11:33 AM}

Hi Grace,

Thanks. I had checked the settings under General Settings for outgoing mail but not for the web application itself. Workflow emails are now being generated however regular alerts are not being sent out.

Evy

_{Wednesday, July 24, 2019 1:41 PM}

I stopped the timer jobs and cleared cached files and alerts still not being sent out. I ran the below command to see the status of the timer jobs on the servers. we have 2 app servers and 2 web servers.

In SQL server ran on content database Select *fromTimerlock. It shows a lock on 02** server since March. Restarted timer service and still shows with same server and date as locked.

Add-PSSnapin Microsoft.SharePoint.Powershell
$farm = Get-SPFarm
$FarmTimers = $farm.TimerService.Instances
foreach ($FT in $FarmTimers)
{
write-host "Server: " $FT.Server.Name.ToString();
write-host "Status: " $FT.status;
write-host "Allow Service Jobs: " $FT.AllowServiceJobs;
write-host "Allow Content DB Jobs: " $FT.AllowContentDatabaseJobs;"`n"
}

Results:

Server: 01**** (app 1)
Status: Online
Allow Service Jobs: True
Allow Content DB Jobs: True

Server: 01****** (app 2
Status: Online
Allow Service Jobs: True
Allow Content DB Jobs: True

Server: 02**** (fe 1)
Status: Online
Allow Service Jobs: False
Allow Content DB Jobs: False

Server: 04**** (fe 2)
Status: Online
Allow Service Jobs: False
Allow Content DB Jobs: False

In SQL server ran on content database Select *fromTimerlock. It shows a lock on 02** server since March. Restarted timer service and still shows with same server and date as locked.

Evy

_{Wednesday, July 24, 2019 6:18 PM}

I was able to get alerts working again.

checked the Immediate Alert timer job and showed as Last Run time na.

Using an article found, I ran the below script on the SQL server content database.

shows you the server and the last time alerts were sent. my case back in June

SELECT * FROM timerlock WITH (nolock)

shows you all the pending alerts.

SELECT * FROM eventcache WITH (nolock) WHERE EventData is not null

the result shows you which server has the lock on the alerts. Using CA, Manage Servers in this farm, hoover over the server names to see the quid id.

Disconnect that server from the farm by running psconfig and select disconnect.

Cleared cache on all server.

Connected server back to the farm.

SUCCESS!!! Alerts being received.

Ran query again and saw updated date

SELECT * FROM timerlock WITH (nolock)

Evy

_{Thursday, July 25, 2019 1:32 AM}

Hi Evy,

Thanks for sharing your solution with us, we can learn more from your post.

You can mark your post as answer to help more community members to find the information quickly.

Thanks for your understanding.