Build 9476 Binding Issue

Problem reported by Al Weedman - 12/15/2025 at 2:40 PM

Resolved

Hi. I updated to 9476 this afternoon. TLS binding issues with outbound SMTP ever since:

12:39:31.083 [127.0.0.1][48917913] rsp: 220 Start TLS negotiation

12:39:31.088 [127.0.0.1][48917913] rsp: 554 Security failure

12:39:31.089 [127.0.0.1][48917913] Exception negotiating TLS session: System.Security.Authentication.AuthenticationException: Authentication failed, see inner exception.

---> System.ComponentModel.Win32Exception (0x80090326): The message received was unexpected or badly formatted.

--- End of inner exception stack trace ---

at System.Net.Security.SslStream.ForceAuthenticationAsync[TIOAdapter](Boolean receiveFirst, Byte[] reAuthenticationData, CancellationToken cancellationToken)

at System.Net.Security.SslStream.AuthenticateAsServer(SslServerAuthenticationOptions sslServerAuthenticationOptions)

at SmarterMail.Protocols.Common.PooledTcpItem.ConvertToSSL(db_system_binding_port setting, Log log, String sessionId)

at SmarterMail.Protocols.Common.PooledTcpItem.ConvertToSSL(db_system_binding_port setting)

3 Replies

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Derek Curtis Replied

12/15/2025 at 4:22 PM

Employee Post

Hi, Al

No other changes were made to any bindings or anything? New hardware?

Derek Curtis COO SmarterTools Inc. www.smartertools.com

Al Weedman Replied

12/15/2025 at 6:54 PM

Derek,

Nothing new between morning and afternoon. I did get things working though. I finagled with a few settings so I'm not positive that this was the issue. Our Outbound IP was set to Primary IP on NIC. I switched it to the IP Address on the LAN and outbound emails are now working.

Derek Curtis Replied

12/16/2025 at 9:28 AM

Employee Post Marked As Resolution

Glad you got it figured out, Al. I'll make sure we look at this, though, just in case. Appreciate you following up.

Derek Curtis COO SmarterTools Inc. www.smartertools.com

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