Help, Can't send to SMTP using SmtpClient using SSL on port 465

[Rob Dob]

The following code is giving me a timeout problem., no matter what I do I
can't send a piece of mail using .net2.0 System.Net.Mail.SmtpClient via port
465 and using ssl, if however I try using outlook or outlook express it
works fine..

System.Net.Mail.MailMessage msgMail = new
System.Net.Mail.MailMessage("my*****@mydomain.com" ,
"te*******@mydomain.com", "subject", "message body");

SmtpClient smtp = new SmtpClient("smtp.postoffice.net", 465);

smtp.EnableSsl = true;

smtp.UseDefaultCredentials = false;

smtp.DeliveryMethod = SmtpDeliveryMethod.Network;

smtp.Credentials = new System.Net.NetworkCredential(my*****@mydomain.com,
"mypassword");

try

{

// the following line is where it times out

smtp.Send(msgMail);

}

catch (Exception ex)

{

}

I also did a trace log and this is what it looks like...

System.Net Information: 0 : [5260] Associating MailMessage#61058004 with
Message#63255637
System.Net Verbose: 0 : [5260] SmtpClient::.ctor(host=smtp.postoffice.net,
port=465)
System.Net Information: 0 : [5260] Associating SmtpClient#27931403 with
SmtpTransport#48953616
System.Net Verbose: 0 : [5260] Exiting SmtpClient::.ctor() ->
SmtpClient#27931403
System.Net Verbose: 0 : [5260]
SmtpClient#27931403::Send(MailMessage#61058004)
System.Net Information: 0 : [5260]
SmtpClient#27931403::Send(DeliveryMethod=Network)
System.Net Information: 0 : [5260] Associating SmtpClient#27931403 with
MailMessage#61058004
System.Net Information: 0 : [5260] Associating SmtpTransport#48953616 with
SmtpConnection#55429074
System.Net Information: 0 : [5260] Associating SmtpConnection#55429074 with
ServicePoint#11280399
System.Net Information: 0 : [5260] Associating SmtpConnection#55429074 with
SmtpPooledStream#37855919
System.Net Error: 0 : [5260] Exception in the SmtpClient#27931403::Send -
Unable to read data from the transport connection: A blocking operation was
interrupted by a call to WSACancelBlockingCall.
System.Net Error: 0 : [5260] at
System.Net.Sockets.NetworkStream.Read(Byte[] buffer, Int32 offset, Int32
size)
at System.Net.DelegatedStream.Read(Byte[] buffer, Int32 offset, Int32
count)
at System.Net.BufferedReadStream.Read(Byte[] buffer, Int32 offset, Int32
count)
at System.Net.Mail.SmtpReplyReaderFactory.ReadLines(S mtpReplyReader
caller, Boolean oneLine)
at System.Net.Mail.SmtpReplyReaderFactory.ReadLine(Sm tpReplyReader
caller)
at System.Net.Mail.SmtpReplyReader.ReadLine()
at System.Net.Mail.SmtpConnection.GetConnection(Strin g host, Int32 port)
at System.Net.Mail.SmtpTransport.GetConnection(String host, Int32 port)
at System.Net.Mail.SmtpClient.GetConnection()
at System.Net.Mail.SmtpClient.Send(MailMessage message)
System.Net Verbose: 0 : [5260] Exiting SmtpClient#27931403::Send()

[Rob Dob]

Thanks, but this is just test code, when I trace it through the debugger I
get a timout exception thrown.. do you have any idea as to why I cannot get
SmtpClient working with SSL and 465?

Thanks,

[Eugene Mayevski]

Hello!
You wrote on Fri, 11 Jan 2008 08:44:48 -0500:

RDThanks, but this is just test code, when I trace it through the
RDdebugger I get a timout exception thrown.. do you have any idea as to
RDwhy I cannot get SmtpClient working with SSL and 465?

Does your server use implicit or explicit SSL/TLS? I don't know which one
SmtpClient class support but it looks like it supports not the one that your
server uses.

Our SMTP client component supports both imlicit and explicit TLS. See http://www.eldos.com/sbb/desc-ssl-features.php
With best regards,
Eugene Mayevski
http://www.SecureBlackbox.com - the comprehensive component suite for
network security

[Rob Dob]

Does your server use implicit or explicit SSL/TLS? I don't know which one

SmtpClient class support but it looks like it supports not the one that
your server uses.

I'm trying to connect with the usa.net mail server, which is
smtp.postoffice.net I would assume it support both, aswell I have tried
this with both tls on and tls off using my own mail server.. no cigar.. Do
you see anything wrong with my code?

thanks,

[sloan]

Try 587.

Download the code from here:
http://sholliday.spaces.live.com/Blog/cns!A68482B9628A842A!138.entry

and see if you can tweak the settings to work with your setup.

"Rob Dob" <ro************@yahoo.comwrote in message
news:uK**************@TK2MSFTNGP06.phx.gbl...

>

The following code is giving me a timeout problem., no matter what I do I
can't send a piece of mail using .net2.0 System.Net.Mail.SmtpClient via
port 465 and using ssl, if however I try using outlook or outlook express
it works fine..

System.Net.Mail.MailMessage msgMail = new
System.Net.Mail.MailMessage("my*****@mydomain.com" ,
"te*******@mydomain.com", "subject", "message body");

SmtpClient smtp = new SmtpClient("smtp.postoffice.net", 465);

smtp.EnableSsl = true;

smtp.UseDefaultCredentials = false;

smtp.DeliveryMethod = SmtpDeliveryMethod.Network;

smtp.Credentials = new System.Net.NetworkCredential(my*****@mydomain.com,
"mypassword");

try

{

// the following line is where it times out

smtp.Send(msgMail);

}

catch (Exception ex)

{

}

I also did a trace log and this is what it looks like...

System.Net Information: 0 : [5260] Associating MailMessage#61058004 with
Message#63255637
System.Net Verbose: 0 : [5260] SmtpClient::.ctor(host=smtp.postoffice.net,
port=465)
System.Net Information: 0 : [5260] Associating SmtpClient#27931403 with
SmtpTransport#48953616
System.Net Verbose: 0 : [5260] Exiting SmtpClient::.ctor() ->
SmtpClient#27931403
System.Net Verbose: 0 : [5260]
SmtpClient#27931403::Send(MailMessage#61058004)
System.Net Information: 0 : [5260]
SmtpClient#27931403::Send(DeliveryMethod=Network)
System.Net Information: 0 : [5260] Associating SmtpClient#27931403 with
MailMessage#61058004
System.Net Information: 0 : [5260] Associating SmtpTransport#48953616 with
SmtpConnection#55429074
System.Net Information: 0 : [5260] Associating SmtpConnection#55429074
with ServicePoint#11280399
System.Net Information: 0 : [5260] Associating SmtpConnection#55429074
with SmtpPooledStream#37855919
System.Net Error: 0 : [5260] Exception in the SmtpClient#27931403::Send -
Unable to read data from the transport connection: A blocking operation
was interrupted by a call to WSACancelBlockingCall.
System.Net Error: 0 : [5260] at
System.Net.Sockets.NetworkStream.Read(Byte[] buffer, Int32 offset, Int32
size)
at System.Net.DelegatedStream.Read(Byte[] buffer, Int32 offset, Int32
count)
at System.Net.BufferedReadStream.Read(Byte[] buffer, Int32 offset, Int32
count)
at System.Net.Mail.SmtpReplyReaderFactory.ReadLines(S mtpReplyReader
caller, Boolean oneLine)
at System.Net.Mail.SmtpReplyReaderFactory.ReadLine(Sm tpReplyReader
caller)
at System.Net.Mail.SmtpReplyReader.ReadLine()
at System.Net.Mail.SmtpConnection.GetConnection(Strin g host, Int32 port)
at System.Net.Mail.SmtpTransport.GetConnection(String host, Int32 port)
at System.Net.Mail.SmtpClient.GetConnection()
at System.Net.Mail.SmtpClient.Send(MailMessage message)
System.Net Verbose: 0 : [5260] Exiting SmtpClient#27931403::Send()

[Rob Dob]

Try 587.

>
Download the code from here:
http://sholliday.spaces.live.com/Blog/cns!A68482B9628A842A!138.entry

Hi,

telnet smtp.postoffice.net 587 does not connect, it appears that this smtp
server only accepts connections on port 465. Also this application is a C#
winform application..

does you have any other suggestions, this is really frustrating..

thanks,

[Eugene Mayevski]

Hello!
You wrote on Fri, 11 Jan 2008 09:27:19 -0500:

RDI'm trying to connect with the usa.net mail server, which is
RDsmtp.postoffice.net I would assume it support both, aswell I have
RDtried this with both tls on and tls off using my own mail server.. no
RDcigar.. Do you see anything wrong with my code?

All I can tell you is that usa.net SMTP uses implicit TLS on port 465 and
explicit TLS on port 25 (pretty standard way).
I've checked our client in both modes and it worked fine. I can say nothing
about .NET class.

With best regards,
Eugene Mayevski
http://www.SecureBlackbox.com - the comprehensive component suite for
network security

[Rob Dob]

What is the best foru to post in to get an answer for this question, I'm
sure there must be some sort of answer?

thanks,