Radarr: Problem Mail connect

[v1ru535]

Hi all,

I wanted to test the mail notifications on my own mail server and I have this error in the logs:

radarr     | [Error] EmailService: Error sending email. Subject: Radarr - Test Notification
radarr     | [Error] EmailService: Unable to send test email: Message could not be sent.
radarr     | [v0.2.0.1120] System.Net.Mail.SmtpException: Message could not be sent. ---> System.AggregateException: One or more errors occurred. ---> System.Security.Authentication.AuthenticationException: A call to SSPI failed, see inner exception. ---> Mono.Btls.MonoBtlsException: Ssl error:1000042e:SSL routines:OPENSSL_internal:TLSV1_ALERT_PROTOCOL_VERSION
radarr     |   at /build/mono-5.12.0.226/external/boringssl/ssl/tls_record.c:462
radarr     |   at Mono.Btls.MonoBtlsContext.ProcessHandshake () [0x00038] in <fc308f916aec4e4283e0c1d4b761760a>:0
radarr     |   at Mono.Net.Security.MobileAuthenticatedStream.ProcessHandshake (Mono.Net.Security.AsyncOperationStatus status) [0x0003e] in <fc308f916aec4e4283e0c1d4b761760a>:0
radarr     |   at (wrapper remoting-invoke-with-check) Mono.Net.Security.MobileAuthenticatedStream.ProcessHandshake(Mono.Net.Security.AsyncOperationStatus)
radarr     |   at Mono.Net.Security.AsyncHandshakeRequest.Run (Mono.Net.Security.AsyncOperationStatus status) [0x00006] in <fc308f916aec4e4283e0c1d4b761760a>:0
radarr     |   at Mono.Net.Security.AsyncProtocolRequest+<ProcessOperation>d__24.MoveNext () [0x000ff] in <fc308f916aec4e4283e0c1d4b761760a>:0
radarr     | --- End of stack trace from previous location where exception was thrown ---
radarr     |   at System.Runtime.CompilerServices.TaskAwaiter.ThrowForNonSuccess (System.Threading.Tasks.Task task) [0x0003e] in <71d8ad678db34313b7f718a414dfcb25>:0
radarr     |   at System.Runtime.CompilerServices.TaskAwaiter.HandleNonSuccessAndDebuggerNotification (System.Threading.Tasks.Task task) [0x00028] in <71d8ad678db34313b7f718a414dfcb25>:0
radarr     |   at System.Runtime.CompilerServices.TaskAwaiter.ValidateEnd (System.Threading.Tasks.Task task) [0x00008] in <71d8ad678db34313b7f718a414dfcb25>:0
radarr     |   at System.Runtime.CompilerServices.ConfiguredTaskAwaitable+ConfiguredTaskAwaiter.GetResult () [0x00000] in <71d8ad678db34313b7f718a414dfcb25>:0
radarr     |   at Mono.Net.Security.AsyncProtocolRequest+<StartOperation>d__23.MoveNext () [0x0008b] in <fc308f916aec4e4283e0c1d4b761760a>:0
radarr     |    --- End of inner exception stack trace ---
radarr     |   at Mono.Net.Security.MobileAuthenticatedStream+<ProcessAuthentication>d__47.MoveNext () [0x00254] in <fc308f916aec4e4283e0c1d4b761760a>:0
radarr     |    --- End of inner exception stack trace ---
radarr     |   at System.Threading.Tasks.Task.ThrowIfExceptional (System.Boolean includeTaskCanceledExceptions) [0x00011] in <71d8ad678db34313b7f718a414dfcb25>:0
radarr     |   at System.Threading.Tasks.Task.Wait (System.Int32 millisecondsTimeout, System.Threading.CancellationToken cancellationToken) [0x00043] in <71d8ad678db34313b7f718a414dfcb25>:0
radarr     |   at System.Threading.Tasks.Task.Wait () [0x00000] in <71d8ad678db34313b7f718a414dfcb25>:0
radarr     |   at Mono.Net.Security.MobileAuthenticatedStream.AuthenticateAsClient (System.String targetHost, System.Security.Cryptography.X509Certificates.X509CertificateCollection clientCertificates, System.Security.Authentication.SslProtocols enabledSslProtocols, System.Boolean checkCertificateRevocation) [0x0000d] in <fc308f916aec4e4283e0c1d4b761760a>:0
radarr     |   at System.Net.Mail.SmtpClient.InitiateSecureConnection () [0x00059] in <fc308f916aec4e4283e0c1d4b761760a>:0
radarr     |   at System.Net.Mail.SmtpClient.SendCore (System.Net.Mail.MailMessage message) [0x000a0] in <fc308f916aec4e4283e0c1d4b761760a>:0
radarr     |   at System.Net.Mail.SmtpClient.SendInternal (System.Net.Mail.MailMessage message) [0x00050] in <fc308f916aec4e4283e0c1d4b761760a>:0
radarr     |   at System.Net.Mail.SmtpClient.Send (System.Net.Mail.MailMessage message) [0x00084] in <fc308f916aec4e4283e0c1d4b761760a>:0
radarr     |    --- End of inner exception stack trace ---
radarr     |   at System.Net.Mail.SmtpClient.Send (System.Net.Mail.MailMessage message) [0x0009f] in <fc308f916aec4e4283e0c1d4b761760a>:0
radarr     |   at NzbDrone.Core.Notifications.Email.EmailService.Send (System.Net.Mail.MailMessage email, System.String server, System.Int32 port, System.Boolean ssl, System.Net.NetworkCredential credentials) [0x00017] in C:\projects\radarr-usby1\src\NzbDrone.Core\Notifications\Email\EmailService.cs:58
radarr     |   at NzbDrone.Core.Notifications.Email.EmailService.SendEmail (NzbDrone.Core.Notifications.Email.EmailSettings settings, System.String subject, System.String body, System.Boolean htmlBody) [0x000a5] in C:\projects\radarr-usby1\src\NzbDrone.Core\Notifications\Email\EmailService.cs:48
radarr     |   at NzbDrone.Core.Notifications.Email.EmailService.Test (NzbDrone.Core.Notifications.Email.EmailSettings settings) [0x00000] in C:\projects\radarr-usby1\src\NzbDrone.Core\Notifications\Email\EmailService.cs:67
radarr     |
radarr     | [Warn] NzbDroneErrorPipeline: Invalid request Validation failed:
radarr     |  -- Unable to send test email

I've configured port 587 with SSL on the interface.
All tests are ok for my mailserver (mail-tester.com 10/10).

In view of this line:
radarr | [v0.2.0.1120] System.Net.Mail.SmtpException: Message could not be sent. ---> System.AggregateException: One or more errors occurred. ---> System.Security.Authentication.AuthenticationException: A call to SSPI failed, see inner exception. ---> Mono.Btls.MonoBtlsException: Ssl error:1000042e:SSL routines:OPENSSL_internal:TLSV1_ALERT_PROTOCOL_VERSION

Can you tell me if this is a TLS version on mail or radarr problem or other issue please?

Thanks in advance.

[v1ru535]

Up maybe?

[v1ru535]

Also,
On my mailserver, you can see:
SSL_do_handshake() failed (SSL: error:1402710B:SSL routines:ACCEPT_SR_CLNT_HELLO_C:wrong version number) while in starttls state, client: **** using starttls, server: 0.0.0.0:587

So, I think radarr must support TLS1.1 or above.
The problem is: given TLS vulnerability and the status of downgrade attacks

Thanks for your reply.

[galli-leo]

Radarr should support 1.1 gladly. Try upgrading your mono version.

[v1ru535]

Thx @galli-leo

I've check mono version:

Mono JIT compiler version 5.14.0.177 (tarball Mon Aug  6 09:13:43 UTC 2018)
Copyright (C) 2002-2014 Novell, Inc, Xamarin Inc and Contributors. www.mono-project.com
        TLS:           __thread
        SIGSEGV:       altstack
        Notifications: epoll
        Architecture:  amd64
        Disabled:      none
        Misc:          softdebug
        Interpreter:   yes
        LLVM:          yes(3.6.0svn-mono-/)
        GC:            sgen (concurrent by default)

So, the version is up to date, like my Radarr version:

Radarr Ver. 0.2.0.1120
develop

Also, I use docker-compose on repo "linuxserver/radarr"

New tests and same results, I don't understand :/

Edit: add version mono (quotes escape version :/)

[markus101]

Are you trying to using implicit SSL/TLS (generally port 465) or SMTP with STARTTLS (port 587)? .net's SmtpClient (which Sonarr and Radarr both use) only supports the latter, which in my understanding starts without a secure connection then upgrades to a secure connection.

Under mono I have no problems sending an email through gmail using SMTP with STARTTLS over port 587.

[v1ru535]

@markus101 I want to use port 587 with starttls, but 465 fail on my side too.

If you're ok with port 587 on gmail on your side, it's not a problem on Radarr or mono.
So, I close this issue for now, but I don't understand...

Thx