Sending email to 365 server

[zsleo]

Here is an extract code I am using/testing that keeps returning the error: 'Socket Error # 10060'#$D#$A'Connection timed out.'

Code:

procedure TForm1.Button1Click(Sender: TObject);
var
  idSMTP1: TIdSMTP;
  idSASLLogin: TIdSASLLogin;
  idUserPassProvider: TIdUserPassProvider;
begin
  idSMTP1 := TIdSMTP.Create(nil);
  try
    idSMTP1.IOHandler := TIdSSLIOHandlerSocketOpenSSL.Create(idSMTP1);
    idSMTP1.UseTLS := utUseExplicitTLS;
    TIdSSLIOHandlerSocketOpenSSL(idSMTP1.IOHandler).SSLOptions.SSLVersions := [sslvTLSv1_2];

    idSMTP1.Host := 'smtp.office365.com';
    idSMTP1.Port := 587;

    idSASLLogin := TIdSASLLogin.Create(idSMTP1);
    idUserPassProvider := TIdUserPassProvider.Create(idSASLLogin);

    idSASLLogin.UserPassProvider := idUserPassProvider;
    idUserPassProvider.Username := 'XXXXXX';
    idUserPassProvider.Password := 'YYYYYY';

    idSMTP1.AuthType := satSASL;
    idSMTP1.SASLMechanisms.Add.SASL := idSASLLogin;

    try
      idSMTP1.Connect;
      try
        idSMTP1.Authenticate;
      finally
        idSMTP1.Disconnect;
      end;
      ShowMessage('OK');
    except
      on E: Exception do
      begin
        ShowMessage(Format('Failed!'#13'[%s] %s', [E.ClassName, E.Message]));
        raise;
      end;
    end;
  finally
    idSMTP1.Free;
  end;

end;

Can someone please help by pointing to what/where I going wrong

TIA

[rlebeau]

Here is an extract code I am using/testing that keeps returning the error: 'Socket Error # 10060'#$D#$A'Connection timed out.'

The code looks fine to me.

Did you verify with a packet sniffer, like Wireshark, that Indy is actually connecting to port 587, and is attempting to use TLS 1.2? Which version of the OpenSSL DLLs are you using?

On which line of code does the error happen on? What does the call stack look like when the error happens?

How long does it take to time out? TIdSSLIOHandlerSocketOpenSSL does use a 30 second timeout on Windows Vista+ if its ReadTimeout property is <= 0 (which it is by default).

[zsleo]

Did you verify with a packet sniffer, like Wireshark, that Indy is actually connecting to port 587, and is attempting to use TLS 1.2?
[ZSL] I will with WireShark later today

Which version of the OpenSSL DLLs are you using?
[ZSL] openssl-1.0.2u-x64_86-win64

On which line of code does the error happen on?
[ZSL] error at "idSMTP1.Connect;"

What does the call stack look like when the error happens?
[ZSL] Callstack:
main thread ($30ac):
0068b8cb +073 Prj2.exe IdStack 929 +54 TIdStack.RaiseSocketError
0068b852 +016 Prj2.exe IdStack 852 +1 TIdStack.RaiseLastSocketError
0068b7bd +015 Prj2.exe IdStack 826 +2 TIdStack.CheckForSocketError
006879b4 +0b0 Prj2.exe IdStackWindows 2026 +20 TIdStackWindows.Connect
0069f351 +02d Prj2.exe IdSocketHandle 295 +1 TIdSocketHandle.Connect
006aa38d +1cd Prj2.exe IdIOHandlerStack 349 +52 TIdIOHandlerStack.ConnectClient
006eab2d +031 Prj2.exe IdSSLOpenSSL 2764 +8 TIdSSLIOHandlerSocketOpenSSL.ConnectClient
006ad9bb +063 Prj2.exe IdIOHandlerSocket 369 +13 TIdIOHandlerSocket.Open
006eac3f +007 Prj2.exe IdSSLOpenSSL 2800 +1 TIdSSLIOHandlerSocketOpenSSL.Open
006a963c +258 Prj2.exe IdTCPClient 327 +54 TIdTCPClientCustom.Connect
006b3ac4 +0a4 Prj2.exe IdExplicitTLSClientServerBase 257 +23 TIdExplicitTLSClient.Connect
006d116b +017 Prj2.exe IdSMTP 377 +2 TIdSMTP.Connect
006eecc1 +125 Prj2.exe Unit1 59 +21 TForm1.Button1Click
005af1ff +073 Prj2.exe Vcl.Controls 7536 +9 TControl.Click
005c6af6 +01e Prj2.exe Vcl.StdCtrls 5470 +3 TCustomButton.Click
005c760c +00c Prj2.exe Vcl.StdCtrls 5931 +1 TCustomButton.CNCommand
005aeca6 +2be Prj2.exe Vcl.Controls 7420 +91 TControl.WndProc
005b375b +63b Prj2.exe Vcl.Controls 10278 +166 TWinControl.WndProc
005c67a0 +06c Prj2.exe Vcl.StdCtrls 5307 +13 TButtonControl.WndProc
005ae8e0 +024 Prj2.exe Vcl.Controls 7198 +10 TControl.Perform
005b38bf +023 Prj2.exe Vcl.Controls 10347 +12 DoControlMsg
005b4343 +00b Prj2.exe Vcl.Controls 10622 +1 TWinControl.WMCommand
006580b9 +045 Prj2.exe Vcl.Forms 6488 +6 TCustomForm.WMCommand
005aeca6 +2be Prj2.exe Vcl.Controls 7420 +91 TControl.WndProc
005b375b +63b Prj2.exe Vcl.Controls 10278 +166 TWinControl.WndProc
00654d39 +64d Prj2.exe Vcl.Forms 4652 +209 TCustomForm.WndProc
005b2d28 +02c Prj2.exe Vcl.Controls 9977 +3 TWinControl.MainWndProc
004e9b08 +014 Prj2.exe System.Classes 17956 +8 StdWndProc
75e743fe +11e USER32.dll SendMessageW
75e744da +07a USER32.dll CallWindowProcW
005b386a +0e6 Prj2.exe Vcl.Controls 10319 +30 TWinControl.DefaultHandler
005af64c +010 Prj2.exe Vcl.Controls 7669 +1 TControl.WMLButtonUp
005aeca6 +2be Prj2.exe Vcl.Controls 7420 +91 TControl.WndProc
005b375b +63b Prj2.exe Vcl.Controls 10278 +166 TWinControl.WndProc
005c67a0 +06c Prj2.exe Vcl.StdCtrls 5307 +13 TButtonControl.WndProc
005b2d28 +02c Prj2.exe Vcl.Controls 9977 +3 TWinControl.MainWndProc
004e9b08 +014 Prj2.exe System.Classes 17956 +8 StdWndProc
75e73ebb +00b USER32.dll DispatchMessageW
0065e727 +0f3 Prj2.exe Vcl.Forms 10747 +23 TApplication.ProcessMessage
0065e76a +00a Prj2.exe Vcl.Forms 10777 +1 TApplication.HandleMessage
0065ea9d +0c9 Prj2.exe Vcl.Forms 10915 +26 TApplication.Run
006fb3fd +049 Prj2.exe Prj2 14 +4 initialization
75d36357 +017 KERNEL32.DLL BaseThreadInitThunk

How long does it take to time out? TIdSSLIOHandlerSocketOpenSSL does use a 30 second timeout on Windows Vista+ if its ReadTimeout property is <= 0 (which it is by default).
[ZSL] after about 30 seconds

[rlebeau]

On which line of code does the error happen on?
[ZSL] error at "idSMTP1.Connect;"

What does the call stack look like when the error happens?
[ZSL] Callstack:
main thread ($30ac):
0068b8cb +073 Prj2.exe    IdStack                        929  +54 TIdStack.RaiseSocketError
0068b852 +016 Prj2.exe    IdStack                        852  +1 TIdStack.RaiseLastSocketError
0068b7bd +015 Prj2.exe    IdStack                        826  +2 TIdStack.CheckForSocketError
006879b4 +0b0 Prj2.exe    IdStackWindows                2026  +20 TIdStackWindows.Connect
<snip>

That trace means that Indy is attempting a direct TCP connection to the specified Host/Port, so a timeout on that operation at the OS layer means that either:

• you don't have a viable network router to that Host (or to a DNS server that can resolve that Host name to an IP). Can you ping the server?
  
• you are not actually connecting to the correct Host/Port to begin with (which goes back to my suggestion to verify that with a sniffer).
  
• the TCP handshake is getting lost and not being completed (which a sniffer will also see).
  

How long does it take to time out?  TIdSSLIOHandlerSocketOpenSSL does use a 30 second timeout on Windows Vista+ if its ReadTimeout property is <= 0 (which it is by default).
[ZSL] after about 30 seconds

The timeout in question that TIdSSLIOHandlerSocketOpenSSL uses internally only applies after the TCP connection has been established and the SSL/TLS handshake is in progress. You are not even getting that far, there is no TCP connection being established.

[zsleo]

Thank you for your help.

Turns out the firewall for the network segment I am on had port 587 blocked... All is good now!