[MonoDevelop] Recent gmail smtp RemoteCertificateChainErrors error

Adam Connelly adam.rpconnelly at gmail.com
Mon Jul 1 21:43:58 UTC 2013


Just to say that this is the monodevelop (the IDE) list, not the list for
the mono framework itself. If you take a look at
http://www.mono-project.com/Mailing_Lists it's got the list of mono mailing
lists. I'm guessing you probably want mono-list.

Hope that helps,

On 1 Jul 2013, at 18:34, Guido Van Hoecke <guivho at gmail.com> wrote:


Recently I get following error when trying to send mail from my Mono
ASP.net app via Gmail SMTP:

] SSL authentication error: RemoteCertificateChainErrors
] Description: HTTP 500. Error processing request.
] Stack Trace:
] System.InvalidOperationException: SSL authentication error:
] at System.Net.Mail.SmtpClient.<callback>m__4 (System.Object sender,
System.Security.Cryptography.X509Certificates.X509Certificate certificate,
System.Security.Cryptography.X509Certificates.X509Chain chain,
SslPolicyErrors sslPolicyErrors) [0x00000] in <filename unknown>:0
] at
(System.Security.Cryptography.X509Certificates.X509Certificate cert,
System.Int32[] certErrors) [0x00000] in <filename unknown>:0
] at
(System.Security.Cryptography.X509Certificates.X509Certificate certificate,
System.Int32[] errors) [0x00000] in <filename unknown>:0
] at
(System.Security.Cryptography.X509Certificates.X509Certificate certificate,
System.Int32[] errors) [0x00000] in <filename unknown>:0
] at
(System.Security.Cryptography.X509Certificates.X509Certificate certificate,
System.Int32[] certificateErrors) [0x00000] in <filename unknown>:0
] at
(Mono.Security.X509.X509CertificateCollection certificates) [0x00000] in
<filename unknown>:0
] at
() [0x00000] in <filename unknown>:0
] at Mono.Security.Protocol.Tls.Handshake.HandshakeMessage.Process ()
[0x00000] in <filename unknown>:0
] at (wrapper remoting-invoke-with-check)
Mono.Security.Protocol.Tls.Handshake.HandshakeMessage:Process ()
] at
(Mono.Security.Protocol.Tls.TlsStream handMsg) [0x00000] in <filename
] at
(IAsyncResult asyncResult) [0x00000] in <filename unknown>:0

I get this error in a web page that's been working for a couple of years

Here's the method I use to create and send the mail:

       public static bool HtmlMail (string @from, string to, string bcc,
string subject, IEnumerable<string> attachments, string htmlBody)
           var mail = new MailMessage { From = new MailAddress (@from) };
           mail.To.Add (to);
           if (bcc.Length > 0)
               mail.Bcc.Add (bcc);
           mail.Subject = subject;
           mail.Body = htmlBody;
           mail.IsBodyHtml = true;
           foreach (var attachment in attachments) {
               mail.Attachments.Add (new Attachment (attachment));
           var smtp = new SmtpClient {
               Host = SmtpServer,
               Port = SmtpPort,
               EnableSsl = true,
               UseDefaultCredentials = false,
               Credentials = new NetworkCredential(id, pw)
           try {
               smtp.Send (mail);
               return true;
           catch (WebException) {
               return false;

Where SmtpServer:SmtpPort are "smtp.gmail.com:587", and the (id, pw)
credentials are correct.

I have tried to follow the suggested approach in the second part of

] mozroots --import --ask-remove
] certmgr -ssl smtps://smtp.gmail.com:465

But the latter is not for tls (port 587) but for plain ssl (port 465)

I have no idea why this app suddenly generates

Any help is most welcome and would be sincerely appreciated!

With kind regards,


Isn't it ironic that many men spend a great part of their lives
avoiding marriage while single-mindedly pursuing those things that
would make them better prospects?
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