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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 System/Network Administrator SmarterTools Inc. (877) 357-6278 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 System/Network Administrator SmarterTools Inc. (877) 357-6278 www.smartertools.com
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