No cleartext SMTP authentication in Server 3.0?

I am currently running OS X Server 2.2.2 on OS X 10.8. I have several Windows clients that use the eM Client E-mail/CalDAV/CardDAV client for mail, calendar and contacts (thsi is just about the only Windows client that works well for all these with OS XServer). Unfortunately this client can only use cleartext authentication for SMTP (it supports MD5 digest for IMAP). I am able to have this working fine via SSL/TLS to OS X Server 2.2.2 for users hosted in Open Directory.
I am now testing OS X Server 3.0.1 running on OS X 10.9.1 and I find to my horror that the SMTP authentication no longer works. IMAP authentication still works okay. It seems either there has been soem change to how SSL/TLS autnentication works on 3.0.1 or cleartest authentication is no longer allowed for SMTP...
Does anyone know if this is indeed a change on the server side? And is there any way to override it and force it to allow cleartext authentication, for Open Directory hosted users, for SMTP (over SSL of course)? If I can't solve this then I am caught between a rock and a hard place.
Thanks for any insights...

Hello MrHoffman,
Thanks for your reply. I have indeed already enabled all those options; my configuration has not changed from 10.8.2/2.2.2 where it all worked just fine (with the same client configuration) :-(
Here is the output from my 10.9.1/3.0.1 server:
bash-3.2# postconf -c /Library/Server/Mail/Config/postfix smtpd_client_restrictions
smtpd_client_restrictions = permit_mynetworks permit_sasl_authenticated reject_rbl_client zen.spamhaus.org permit
bash-3.2# postconf -c /Library/Server/Mail/Config/postfix smtpd_pw_server_security_options
smtpd_pw_server_security_options = cram-md5,digest-md5,gssapi,login,plain
and
bash-3.2# telnet xxx.yyyyyyyyyy.org.uk 25
Trying 10.0.200.6...
Connected to xxx.yyyyyyyyyyy.org.uk.
Escape character is '^]'.
220 xxx.yyyyyyyyyyyy.org.uk ESMTP Postfix
EHLO aaa.yyyyyyyyyyyyyy.org.uk
250-xxx.yyyyyyyyyyyy.org.uk
250-PIPELINING
250-SIZE 31457280
250-VRFY
250-ETRN
250-STARTTLS
250-AUTH LOGIN PLAIN CRAM-MD5 DIGEST-MD5 GSSAPI
250-ENHANCEDSTATUSCODES
250-8BITMIME
250-DSN
250-BINARYMIME
250 CHUNKING
The problem seems to definitely be related to authentication. If I (temporarily) allow unauthenticated submission on port 25 and set the client to not send any credentials then it connects and sumbits successfully.
In 'mail.log' I see these messages (many times):
Jan 2 18:56:13 xxx.yyyyyyyyyyyyy.org.uk postfix/postscreen[13851]: CONNECT from [10.0.200.68]:49293 to [10.0.200.6]:25
Jan 2 18:56:13 xxx.yyyyyyyyyyyyy.org.uk postfix/postscreen[13851]: WHITELISTED [10.0.200.68]:49293
Jan 2 18:56:13 xxx.yyyyyyyyyyyyy.org.uk postfix/smtpd[13852]: connect from aaa.yyyyyyyyyyyyy.org.uk[10.0.200.68]
Jan 2 18:56:13 xxx.yyyyyyyyyyyyy.org.uk postfix/smtpd[13852]: error: verify password: error: Credentials could not be verified, username or password is invalid.
Jan 2 18:56:13 www.thejenkinsfamily.org.uk postfix/smtpd[13852]: error: verify password: authentication failed: user=ddddd
I know this user/password is okay since (a) it can login as a network usr authenticated by Open Directory and (b) it can send mail from OS X Mail authenticating using CRAM-MD5 over SSL.
The eM Client SMTP log shows this...
16:15:51.477|023|   SMTP S: 220 xxx.yyyyyyyyyy.org.uk ESMTP Postfix
16:15:51.477|023|   SMTP C: EHLO [10.0.2.15]
16:15:51.477|023|   SMTP S: 250-xxx.yyyyyyyyyy.org.uk
16:15:51.477|023|   SMTP S: 250-PIPELINING
16:15:51.477|023|   SMTP S: 250-SIZE 31457280
16:15:51.477|023|   SMTP S: 250-VRFY
16:15:51.477|023|   SMTP S: 250-ETRN
16:15:51.477|023|   SMTP S: 250-STARTTLS
16:15:51.477|023|   SMTP S: 250-ENHANCEDSTATUSCODES
16:15:51.477|023|   SMTP S: 250-8BITMIME
16:15:51.477|023|   SMTP S: 250-DSN
16:15:51.477|023|   SMTP S: 250-BINARYMIME
16:15:51.477|023|   SMTP S: 250 CHUNKING
16:15:51.477|023|   SMTP C: STARTTLS
16:15:51.477|023|   SMTP S: 220 2.0.0 Ready to start TLS
16:15:51.477|023|   SMTP C: EHLO [10.0.2.15]
16:15:51.477|023|   SMTP S: 250-xxx.yyyyyyyyyy.org.uk
16:15:51.477|023|   SMTP S: 250-PIPELINING
16:15:51.477|023|   SMTP S: 250-SIZE 31457280
16:15:51.477|023|   SMTP S: 250-VRFY
16:15:51.477|023|   SMTP S: 250-ETRN
16:15:51.477|023|   SMTP S: 250-AUTH LOGIN PLAIN CRAM-MD5 DIGEST-MD5 GSSAPI
16:15:51.477|023|   SMTP S: 250-ENHANCEDSTATUSCODES
16:15:51.477|023|   SMTP S: 250-8BITMIME
16:15:51.477|023|   SMTP S: 250-DSN
16:15:51.477|023|   SMTP S: 250-BINARYMIME
16:15:51.477|023|   SMTP S: 250-CHUNKING
16:15:51.477|023|   SMTP S: 250 BURL
16:15:51.493|023|   SMTP C: AUTH LOGIN
16:15:51.493|023|   SMTP S: 334 VXNlcm5hbWU6
16:15:51.493|023|   SMTP C: Y2hyaXM=
16:15:51.493|023|   SMTP S: 334 UGFzc3dvcmQ6
16:15:51.493|023|   SMTP C: d2VhdmV3MQ==
16:15:51.555|023|   SMTP S: 535 Error: authentication failed
16:15:53.895|023|   SMTP C: AUTH LOGIN
16:15:53.895|023|   SMTP S: 334 VXNlcm5hbWU6
16:15:53.895|023|   SMTP C: Y2hyaXM=
16:15:53.895|023|   SMTP S: 334 UGFzc3dvcmQ6
16:15:53.895|023|   SMTP C: d2VhdmV3MQ==
16:15:53.942|023|   SMTP S: 535 Error: authentication failed
16:15:54.488|023|   SMTP C: AUTH LOGIN
16:15:54.488|023|   SMTP S: 334 VXNlcm5hbWU6
16:15:54.488|023|   SMTP C: Y2hyaXM=
16:15:54.504|023|   SMTP S: 334 UGFzc3dvcmQ6
16:15:54.504|023|   SMTP C: d2VhdmV3MQ==
16:15:54.550|023|   SMTP S: 535 Error: authentication failed
Do you have any insights? I am somewhat stumped at this point... I am wonderign is some subtle change (in OS X Server) has resulted in an incompatibility between eM Client and OS X Server 3.0.
Regards,
Chris

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$headers .= "To: $nameto <$to>" . $newLine;
$headers .= "From: $namefrom <$from>" . $newLine;
fputs($smtpConnect, "To: $to\nFrom: $from\nSubject: $subject\n$headers\n\n$message\n.\n");
$smtpResponse = fgets($smtpConnect, 515);
$logArray['data2response'] = "$smtpResponse";
fputs($smtpConnect,"QUIT" . $newLine);
$smtpResponse = fgets($smtpConnect, 515);
$logArray['quitresponse'] = "$smtpResponse";
function show_error($myError)
?>
    <html>
    <body>
    <b>Please correct the following error:</b><br />
    <?php echo $myError; ?>
    </body>
    </html>
<?php
exit();
?>

I have the same problem - user has Outlook 2010 on Exchange 2007. Mail goes directly into the deleted items folder. After browsing around the net I found 2 different site with the same potential fix. It seems that when migrating a user from Exch 2003 to
2007 (which we did) some of the configs get set incorrectly. The weird thing is we migrated over 2 years ago, and some others are experiencing the same after a long period after the migration. The fix that was suggested is:
Go to your Exch server, open up Exchange Management Shell and type the following:
get-mailboxcalendarsettings "domain/ou/user" | fl
set-mailboxcalendarsettings "doman/ou/user" -automateprocessing: Autoupdate
My user already had Autoupdate set, but this seems to have fixed it for me...

SMTP authentication problem

I try to send mail with a Javamail client code (you can see the code below), it works fine if the mail server doesn't require SMTP authentication to be relay, but SendFailedException occurs if the mail server security setting is set to SMTP requires authentication (same settings as POP usr/pwd) on the mail server.
I believe it is an issue of SMTP authentication.
How do I code for SMTP authentication with Java Mail API?
Thanks!
Can Odabasioglu
Source Code:
import java.util.Properties;
import javax.mail.*;
import javax.mail.internet.*;
import java.io.UnsupportedEncodingException;
public class MailExample {
public static void main (String args[]) {
String host = "odabasioglu.net";
String from = "[email protected]";
String to = "[email protected]";
     try {
     Properties props = System.getProperties();
     Authenticator auth = new POPAuth ();
     props.put("mail.smtp.host", host);
     Session session = Session.getInstance(props, auth);
     MimeMessage message = new MimeMessage(session);
     message.setFrom(new InternetAddress(from,"FromName"));
     message.addRecipient(Message.RecipientType.TO,new InternetAddress(to,"ToName"));
     message.setSubject("Test Subject");
     message.setText("Can Odabasioglu");
     Transport.send(message);
     catch (MessagingException e) {e.toString();}
catch (UnsupportedEncodingException e) {e.toString();}
static class POPAuth extends Authenticator {
public PasswordAuthentication getPasswordAuthentication() {
return new PasswordAuthentication("UserName", "Password");
}

“Cannot send message using the server
Mail.ISP.net:[email protected]”
…And provides the “Send message using:” pulldown to
select one of two accounts (one is followed by
“:[email protected]”, the other is not). Both are the
same options the other two machines have, but neither
option works on this machine.
This is one of those error messages that they send application programmers to school for so that they can include error messages that don't tell you what the problem is.
After much trial and error, I discovered that this message is returned if there is an error in the recipient's email address. Perhaps, if it was stored in the address book, it became corrupt. I've found that manually typing in the address (without automatically finishing it from cache) usually fixes the problem. I just spoke to a customer this morning with the same error message, and entering the recipient's email address manually corrected the problem.

SMTP Authentication Possible?

The SMTP mail server in my environment uses authentication (user/pswd) when connecting and sending e-mail. How can I pass user/pswd to it through Reports? I realize that I can set up a pluginParam to specify the SMTP name. But I can't find anything on SMTP authentication.
Thanks,
Scott

You can always create a custom destination that takes control after the Reports Server formats the report. Your plugin destination does all that Reports mailing destination package does plus authenticate the user.
For more information on how to create and deploy custom destination, visit:
http://otn.oracle.com/products/reports/apis/index.html
Regards
Sripathy

SMTP authentication disabled in Outlook

Hello,
Was a security or outlook update recently released that disabled SMTP authentication in Outlook 2003/2007? I've had several users report that this has been disabled; all are using various flavors of Outlook and Windows.

Hi,
“SMTP requires authentication” option is set when using a POP3, IMAP or HTTP account in Outlook. If you are using Outlook 2007, we need to follow these steps to configure it:
1. On the Tools menu, click Account Settings.
2. Select the account you want to change.
3. Click More Settings, and then you can change the following:
4. On the Outgoing Server tab, you can specify whether your outgoing SMTP mail server requires authentication. This is almost always required if your ISP allows you to send e-mail messages through your ISP e-mail account when you are not
directly connected to the ISP network, for example, if you want to send an e-mail message with your home ISP e-mail account and you are away from home connected to your work network.
For more information about it, please refer to the following article:
http://office.microsoft.com/en-us/outlook-help/change-email-account-settings-HP010006899.aspx#BM2
Regards,
Winnie Liang
TechNet Community Support

SMTP authentication description

Hi everyone :
I don't know what is Ironport SMTP authentication feature after reading the Adv-UserGuide.
Is it the smtp authentication use to authen the user connect to email server and How it work between email server and client if it is , As we know Ironport is email gateway , How Ironport can control the user connect to email server ?
Is it only work for Outgoing email authentication ?
thx thx !

I would say that SMTP Authentication is most commonly used for a segment of your end users that are traveling on business or work outside of the internal company network and can't be connected directly to the company mailserver to send out their outgoing mail.
Since a user outside the network may not be able to directly connect to the corporate mailserver, what mail administrators try to set up is the IronPort appliance to do smtp authentication against an Active Directory server for example and then if the sender authenticates, they'll be able to relay using the IronPort appliance.
If you run into any problems or questions, feel free to post the issue here and we'll try to iron it out.

SMTP Authentication Function

Hi, i want to ask the function of smtp authentication in ironport. Is it used to authenticate with the exchange server or per client using LDAP? When i configure the smtp authentication, is it used for incoming or outgoing connection ? Thanks.
Regards
Alkuin Melvin

Dear Alkuin,
For SMTP authentication configuration, you can configure SMTP auth profile under 'Network'-'SMTP Authentication' (LDAP, forward and outgoing).
In my opinion, you can choose to enable SMTP AUTH in mail flow polic(ies) of existing listener (port 25) and/or a new listener using another port (say port 8025). The reason to use 'port number other than port 25' is that some residential ISP or hotel internet connection will block outgoing port 25 connection (due to antispam reason - blocking botnet/malware infected hosts to send spams and ISP IP address gets blacklisted).
For existing listener, you can configure SMTP AUTH "Preferred" setting in default mail flow policy, and then users can authenticate and then relay emails through IronPort from public IP address (configure email client's outgoing SMTP gateway with IronPort public IP address and port 25). One point to note is that if the user is sending from a poor reputation IP, their SMTP connection may be blocked or throttled.
For listener using port number other than 25 (e.g. 8025) , you can configure to have just one sender group with default mail flow policy configured with SMTP AUTH "Required". The email client needs to configure with outgoing SMTP gateway with IronPort listener's public IP address and specific port number (say port 8025). In this way, only authenticated user can relay emails through this listener and they can avoid port 25 blocking issue or sending host's reputation issue as mentioned above.
Cheers,
Tommy

No cleartext SMTP authentication in Server 3.0?

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