Error sending Email via external smtps

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webcraft posted this 3 weeks ago

I setup an external mail server in AMP. The email isn't send and I get this error:

Unable to send email: System.Net.Mail.SmtpException: Message could not be sent. ---> System.Security.Authentication.AuthenticationException: Authentication failed, see inner exception. ---> Mono.Btls.MonoBtlsException: Ssl error:100000f7:SSL routines:OPENSSL_internal:WRONG_VERSION_NUMBER at /usr/src/mono/external/boringssl/ssl/tls_record.c:217 at Mono.Btls.MonoBtlsContext.ProcessHandshake ()

The login details are correct because I copied them to Outlook and I was able to login using them.

Debian 11 - AMP 2.3.0.8 - TLSv1.2 and v1.3 (both not working)

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webcraft posted this 3 weeks ago

Ok, apparently, newer TLS versions as well as STARTTLS are not supported. Just figured out this is the same when I use TLSv1.3 on the reverse proxy on the controller, the target can no longer communicate. It's a different problem and likely different library that causes this issue but maybe the dependencies can be updated in general at some time to support newer openssl versions.

*Edit: * This is no solution. Sending email via an external exim server on a default Debian 11 setup (Debian package) doesn't work with AMP but works with e.g. Outlook.

webcraft posted this 3 weeks ago

I've tried to connect to ionos which supports multiple tls versions I suppose and this gives me the following error:

Unable to send email: System.Net.Mail.SmtpException: Message could not be sent. ---> System.IO.IOException: Connection closed at System.Net.Mail.SmtpClient.Read ()

If I turn of SSL in the AMP settings and send via port 25, it is working with unchanged credentials. Can you please have a look how to fix the SSL problem? Thanks

Mike posted this 3 weeks ago

It may not be fixable at this time on Linux systems. TLS 1.2 should work fine though. Are you able to turn on full debug logging? https://github.com/CubeCoders/AMP/wiki/Diagnosing-AMP-issues

webcraft posted this 3 weeks ago

This is the error when exim is configured to use STARTTLS:

Unable to send email: System.Net.Mail.SmtpException: Message could not be sent. ---> System.Security.Authentication.AuthenticationException: Authentication failed, see inner exception. ---> Mono.Btls.MonoBtlsException: Ssl error:100000f7:SSL routines:OPENSSL_internal:WRONG_VERSION_NUMBER at /usr/src/mono/external/boringssl/ssl/tls_record.c:217 at Mono.Btls.MonoBtlsContext.ProcessHandshake () [0x00048] in <89c0593a45af442582ca75c3a3483f44>:0 at Mono.Net.Security.MobileAuthenticatedStream.ProcessHandshake (Mono.Net.Security.AsyncOperationStatus status, System.Boolean renegotiate) [0x000da] in <89c0593a45af442582ca75c3a3483f44>:0 at (wrapper remoting-invoke-with-check) Mono.Net.Security.MobileAuthenticatedStream.ProcessHandshake(Mono.Net.Security.AsyncOperationStatus,bool) at Mono.Net.Security.AsyncHandshakeRequest.Run (Mono.Net.Security.AsyncOperationStatus status) [0x00006] in <89c0593a45af442582ca75c3a3483f44>:0 at Mono.Net.Security.AsyncProtocolRequest.ProcessOperation (System.Threading.CancellationToken cancellationToken) [0x000fc] in <89c0593a45af442582ca75c3a3483f44>:0 --- End of inner exception stack trace --- at Mono.Net.Security.MobileAuthenticatedStream.AuthenticateAsClient (System.String targetHost, System.Security.Cryptography.X509Certificates.X509CertificateCollection clientCertificates, System.Security.Authentication.SslProtocols enabledSslProtocols, System.Boolean checkCertificateRevocation) [0x0004b] in <89c0593a45af442582ca75c3a3483f44>:0 at (wrapper remoting-invoke-with-check) Mono.Net.Security.MobileAuthenticatedStream.AuthenticateAsClient(string,System.Security.Cryptography.X509Certificates.X509CertificateCollection,System.Security.Authentication.SslProtocols,bool) at System.Net.Security.SslStream.AuthenticateAsClient (System.String targetHost, System.Security.Cryptography.X509Certificates.X509CertificateCollection clientCertificates, System.Security.Authentication.SslProtocols enabledSslProtocols, System.Boolean checkCertificateRevocation) [0x00006] in <89c0593a45af442582ca75c3a3483f44>:0 at System.Net.Mail.SmtpClient.InitiateSecureConnection () [0x0005b] in <89c0593a45af442582ca75c3a3483f44>:0 at System.Net.Mail.SmtpClient.SendCore (System.Net.Mail.MailMessage message) [0x000a0] in <89c0593a45af442582ca75c3a3483f44>:0 at System.Net.Mail.SmtpClient.SendInternal (System.Net.Mail.MailMessage message) [0x00050] in <89c0593a45af442582ca75c3a3483f44>:0 at System.Net.Mail.SmtpClient.Send (System.Net.Mail.MailMessage message) [0x00084] in <89c0593a45af442582ca75c3a3483f44>:0 --- End of inner exception stack trace --- at System.Net.Mail.SmtpClient+<>c__DisplayClass90_0.<sendasync>b__0 (System.Object o, System.ComponentModel.DoWorkEventArgs ea) [0x0002c] in <89c0593a45af442582ca75c3a3483f44>:0 at System.ComponentModel.BackgroundWorker.OnDoWork (System.ComponentModel.DoWorkEventArgs e) [0x0000a] in <89c0593a45af442582ca75c3a3483f44>:0 at System.ComponentModel.BackgroundWorker.WorkerThreadStart (System.Object argument) [0x0000e] in <89c0593a45af442582ca75c3a3483f44>:0 --- End of stack trace from previous location where exception was thrown --- at EmailSenderPlugin.PluginMain.SendMail (System.String To, System.String Subject, System.String Message, System.Net.Mail.MailPriority Priority) [0x0013f] in <fd2cbd7f73b045439373025011a6e080>:0

And this one with TLSv1.2:

Unable to send email: System.Net.Mail.SmtpException: Message could not be sent. ---> System.IO.IOException: Connection closed at System.Net.Mail.SmtpClient.Read () [0x000bd] in <89c0593a45af442582ca75c3a3483f44>:0 at System.Net.Mail.SmtpClient.SendCore (System.Net.Mail.MailMessage message) [0x00000] in <89c0593a45af442582ca75c3a3483f44>:0 at System.Net.Mail.SmtpClient.SendInternal (System.Net.Mail.MailMessage message) [0x00050] in <89c0593a45af442582ca75c3a3483f44>:0 at System.Net.Mail.SmtpClient.Send (System.Net.Mail.MailMessage message) [0x00084] in <89c0593a45af442582ca75c3a3483f44>:0 --- End of inner exception stack trace --- at System.Net.Mail.SmtpClient+<>c__DisplayClass90_0.<sendasync>b__0 (System.Object o, System.ComponentModel.DoWorkEventArgs ea) [0x0002c] in <89c0593a45af442582ca75c3a3483f44>:0 at System.ComponentModel.BackgroundWorker.OnDoWork (System.ComponentModel.DoWorkEventArgs e) [0x0000a] in <89c0593a45af442582ca75c3a3483f44>:0 at System.ComponentModel.BackgroundWorker.WorkerThreadStart (System.Object argument) [0x0000e] in <89c0593a45af442582ca75c3a3483f44>:0 --- End of stack trace from previous location where exception was thrown --- at EmailSenderPlugin.PluginMain.SendMail (System.String To, System.String Subject, System.String Message, System.Net.Mail.MailPriority Priority) [0x0013f] in <fd2cbd7f73b045439373025011a6e080>:0</fd2cbd7f73b045439373025011a6e080></89c0593a45af442582ca75c3a3483f44></89c0593a45af442582ca75c3a3483f44></89c0593a45af442582ca75c3a3483f44></sendasync></89c0593a45af442582ca75c3a3483f44></89c0593a45af442582ca75c3a3483f44></89c0593a45af442582ca75c3a3483f44></89c0593a45af442582ca75c3a3483f44></fd2cbd7f73b045439373025011a6e080></89c0593a45af442582ca75c3a3483f44></89c0593a45af442582ca75c3a3483f44></89c0593a45af442582ca75c3a3483f44></sendasync></89c0593a45af442582ca75c3a3483f44></89c0593a45af442582ca75c3a3483f44></89c0593a45af442582ca75c3a3483f44></89c0593a45af442582ca75c3a3483f44></89c0593a45af442582ca75c3a3483f44></89c0593a45af442582ca75c3a3483f44></89c0593a45af442582ca75c3a3483f44></89c0593a45af442582ca75c3a3483f44></89c0593a45af442582ca75c3a3483f44></89c0593a45af442582ca75c3a3483f44>

webcraft posted this 2 weeks ago

No, this is not working for me with TLSv1.2.

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