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-Ran mozroots --import --sync, certmgr -ssl url
OS: Ubuntu 14.04 LTS
Nginx 1.7.4 (sha256RSA 2048 bits)
Postfix mail_version = 2.11 (sha256RSA 2048 bits)
C# code to send mail executes (EnableSSL = true;), it throws the following exception
System.Net.Mail.SmtpException: Message could not be sent. ---> System.IO.IOException: The authentication or decryption has failed. ---> System.ArgumentException: certificate ---> System.Security.Cryptography.CryptographicException: Unsupported hash algorithm: 1.2.840.1135188.8.131.52
at Mono.Security.X509.X509Certificate.VerifySignature (System.Security.Cryptography.RSA rsa) [0x00000] in <filename unknown>:0
at Mono.Security.X509.X509Certificate.VerifySignature (System.Security.Cryptography.AsymmetricAlgorithm aa) [0x00000] in <filename unknown>:0
at System.Security.Cryptography.X509Certificates.X509Chain.IsSignedWith (System.Security.Cryptography.X509Certificates.X509Certificate2 signed, System.Security.Cryptography.AsymmetricAlgorithm pubkey) [0x00000] in <filename unknown>:0
at System.Security.Cryptography.X509Certificates.X509Chain.Process (Int32 n) [0x00000] in <filename unknown>:0
at System.Security.Cryptography.X509Certificates.X509Chain.ValidateChain (X509ChainStatus
Problem was mentioned in this thread but that was for Mono 2.10: https://bugzilla.xamarin.com/show_bug.cgi?id=8788
Posting here as the solution:
So I dropped my existing Mono.Security.dll (v184.108.40.206 .NET Framework v4.0) into dotNetPeek (free decompiler) and looked at the code.
Drilled down into code tree: Mono.Security => Mono.Security.X509 => X509Certificate => internal bool VerifySignature(RSA rsa)
The VerifySignature() method only has 4 possible signatures, algorithm: 1.2.840.1135220.127.116.11 not being one of them.
So I went and downloaded the Mono.Security.dll from the npgsql project on github (Npgsql is the .NET data provider for Postgresql): https://github.com/npgsql/npgsql/tree/master/lib/Mono.Security/4.0
Says its was released 3 months ago ~7/22/2014 with note (Update Mono.Security.dll assembly to Mono version 3.4.0)
Loaded new Mono.Security.dll into dotNetPeek and drilled down: Mono.Security => Mono.Security.X509 => X509Certificate => public virtual byte Signature.
Has 10 different signatures and the one I needed (1.2.840.113518.104.22.168) was there.
Delete OLD reference in my project to Mono.Security.dll and emptied bin directory. Add New Reference => Browse => newly downloaded Mono.Security.dll from npgsql github => Clean => Rebuild => Deploy. Sending email works fine now.
Special thanks to the contributors of this project!