Connection Timeout when idSMTP when using TIdSSLIOHandlerSocketOpenSSL

Question

I'm having a problem using TidSMTP with TIdSSLIOHandlerSocketOpenSSL getting "Socket Error" just by connecting to the server.

Here's the Form Component Code

  object IdSMTP: TIdSMTP
    IOHandler = IdSSLIOHandlerSSL
    Port = 465
    SASLMechanisms = <>
    UseTLS = utUseImplicitTLS
    Left = 93
    Top = 49
  end
  object IdSSLIOHandlerSSL: TIdSSLIOHandlerSocketOpenSSL
    OnStatus = IdSSLIOHandlerSSLStatus
    Destination = ':465'
    MaxLineAction = maException
    Port = 465
    DefaultPort = 0
    SSLOptions.Mode = sslmUnassigned
    SSLOptions.VerifyMode = []
    SSLOptions.VerifyDepth = 0
    OnStatusInfo = IdSSLIOHandlerSSLStatusInfo
    Left = 88
    Top = 112
  end

and Delphi Code

 IdSMTP.Username  := 'username';
 IdSMTP.Password  := 'password';
 IdSMTP.Host      := 'domain';
 IdSMTP.Port      := 465;
 IdSMTP.UseTLS    := utUseImplicitTLS;
 try
    IdSMTP.Connect;
 except
    on E:Exception do
       // Socket Error, Connection Timeout is thrown.
       Memo1.Lines.Add(E.Message);
 end;

I logged SSL IO status and got this:

Resolving hostname {domain}.
Connecting to {ip}.
SSL status: "before/connect initialization"
SSL status: "before/connect initialization"
SSL status: "SSLv3 write client hello A"
SSL status: "SSLv3 read server hello A"
Socket Error # 10060
Connection timed out.

Our mail server is using self-signed certificate by the way.

What am i doing wrong?

TIA

UPDATE:07-02-2014

Tried Sending mail to Gmail using Indy tip but i get Connection Closed Gracefully sending the email also after SSLv3 read server hello A.

Resolving hostname smtp.gmail.com.
Connecting to 74.125.25.108.
Connected.
Sending Email..
SSL status: "before/connect initialization"
SSL status: "before/connect initialization"
SSL status: "SSLv3 write client hello A"
SSL status: "SSLv3 read server hello A"
Disconnected.
Connection Closed Gracefully.

Here's the new code:

 IdSMTP.Username  := 'username';
 IdSMTP.Password  := 'password';
 IdSMTP.Host      := 'smtp.gmail.com';
 IdSMTP.UseTLS    := utUseExplicitTLS;
 IdSMTP.Port      := 587;
 try
    // Can connect successfully
    IdSMTP.Connect;

    // This part throws the exception
    IdSMTP.Send(IdMessage);
 except
    on E:Exception do
       // Disconnected, connection closed gracefully 
       Memo1.Lines.Add(E.Message);
 end;

UPDATE:

Tried sending email using Thunderbird connecting to same domain.

Thunderbird: Wireshark capture - Sending email using thunderbird

Indy: Wireshark capture - Using Indy

No "client key exchange, ..." occurred on my program.

SOLVED

This isssue was resolved by Manually setting connectiontimeout

Remy Lebeau Remy Lebeau · Accepted Answer · 2014-07-01T16:27:47

You are using implicit SSL. That means an SSL handshake is initiated as soon as the socket is connected to the server, before any application data (SMTP commands/responses) are exchanged. A client hello is sent to the server, and then a timeout is occurring while waiting for the server to send back a hello in response. That implies that the server is NOT using SSL on the port you are connecting to.

Something to keep in mind - setting the UseTLS property may change the Port property, so make sure the Port is actually what you are expecting when Connect() is called. To make sure, try setting the Port after setting the UseTLS rather than before.

Connection Timeout when idSMTP when using TIdSSLIOHandlerSocketOpenSSL

2 Answers