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SM delivery: A call to SSPI failed
Question asked by Michael Muller - 10/29/2019 at 12:55 PM
Answered
One of my email customers is trying to send emails to @dudleyma.gov and they keep bouncing back.

Looking at the Delivery Log, I see the following:

09:33:22.741 [04797] RSP: 220 Ready to start TLS 09:33:22.772 [04797] Exception: A call to SSPI failed, see inner exception.

Stack: at System.Net.Security.SslState.StartSendAuthResetSignal(ProtocolToken message, AsyncProtocolRequest asyncRequest, Exception exception)
at System.Net.Security.SslState.CheckCompletionBeforeNextReceive(ProtocolToken message, AsyncProtocolRequest asyncRequest)
at System.Net.Security.SslState.ProcessReceivedBlob(Byte[] buffer, Int32 count, AsyncProtocolRequest asyncRequest)
at System.Net.Security.SslState.StartReceiveBlob(Byte[] buffer, AsyncProtocolRequest asyncRequest)
at System.Net.Security.SslState.CheckCompletionBeforeNextReceive(ProtocolToken message, AsyncProtocolRequest asyncRequest)
at System.Net.Security.SslState.ForceAuthentication(Boolean receiveFirst, Byte[] buffer, AsyncProtocolRequest asyncRequest)
at System.Net.Security.SslState.ProcessAuthentication(LazyAsyncResult lazyResult)
at MailService.RelayServer.Clients.SMTP.ClientConnectionSync.InitiateSsl(Boolean validateAllCerts)
at MailService.RelayServer.Clients.SMTP.SmtpClientSession.GiveStartTls(Boolean validateAllCerts)
Inner Exception: The message received was unexpected or badly formatted
Inner Stack:

09:33:22.772 [04797] Attempt to ip, '66.175.58.41' success: 'False'

Is this SSL fail on my end or theirs?

Thanks

(BTW, this editor is very annoying... hitting up-arrow bounces you out of this form and into the tag field, below, which makes no sense)
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Michael Muller Replied
10/29/2019 at 1:00 PM
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Kyle Kerst Replied
10/29/2019 at 2:50 PM
Employee Post
Michael, these errors typically indicate SmarterMail had an issue trying to access the SSL certificate, the private key associated with that SSL certificate, or is experiencing a bigger error in the SSL/TLS cipher suites. Are you seeing anything in the event viewer or logs that might point us in the right direction?
Kyle Kerst IT Coordinator SmarterTools Inc. www.smartertools.com
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Michael Muller Replied
11/4/2019 at 9:09 AM
Marked As Answer
We installed IIS Crypto, which resolved the issue. Apparently our SSL was using a different cipher, as you suggested.
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Kyle Kerst Replied
11/4/2019 at 11:49 AM
Employee Post
That is great news Michael, thanks for updating me on your results. These issues will become more common in the future as older/more insecure versions of these protocols are transitioned out of regular use, so I'm assuming this thread will come in handy for others as well!
Kyle Kerst IT Coordinator SmarterTools Inc. www.smartertools.com
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