Mail 2.0 + SMTP auth + qmail

On our SMTP servers (running qmail), we're currently not requiring SMTP auth, but it does work with other clients...just not with Apple Mail.
If you connect to our SMTP server from another provider's network, there's a notification which tells the client that SMTP auth is required, so it works from another network.
On our own network, however, SMTP auth is not required, so Mail never receives the notification of SMTP auth being possible, so it just times out when trying to authenticate.
This is all on port 25, no SSL/TLS/etc., and all UNs/PWs are in cleartext.
We're going to be requiring SMTP auth in the near future, so I need to figure this out for our Mac users (and myself).
My feeling is that once we require SMTP auth, that notification will go to the client, and it will work, but I'm not sure, and I'm unable to get our admins to give me a test server to play with/test things out.
Any ideas/thoughts?
Thanks in advance...

Hello,
Mail, in all versions, has always timed out whenever a separate, "hard" authentication is not required, but attempted anyway. The difference has always appeared to me to relate to the fact that Mail will perform SMTP after POP3 authentication, WITHOUT having any authentication specified in the outgoing server settings. When the separate authentication is required, it should work fine.
The difference may be that other mail clients stop their authentication actions when connection is successful, without it, but Mail proceeds to do what it is told to do -- if Password authentication is selected, ask no questions, just do it.
In the Mail Setup Assistant now used in Mail 2.0, it is possible to select that the Outgoing Server requires authentication, but then NOT fill in the Password and Username if not needed. As far as I can tell, this does not seem different from specifying None in previous versions.
Ernie

Similar Messages

OS X's Mail app and SMTP auth

We're having a problem with OS X's Mail app connecting to Tiger Server's mail server. We have the server set up to not always require SMTP auth (all SMTP auth settings unchecked in Settings > Advanced > Security), and to allow relay from only a given set of networks (Settings > Relay). In theory, this means that if you're on one of the specified networks, you're not required to authenticate, otherwise you are. This according to Apple's documentation.
From a bit of packet sniffing, it looks like:
1. If a user on an allowed network tries to send mail through the server, the server does not return authorization as an option.
2. If the user has password authentication specified in Mail's SMTP Server settings, it refuses to send. If they set SMTP auth to None, the Mail app will send.
IOW, Mail doesn't send if Authorization is enabled in the Mail app, but not given as an option by the mail server. Has anyone else seen this? Is this a bug in Mail or Postfix?

If you have networks entered in
'Accept SMTP relay only from these hosts and
networks'
Clients on these networks don't need to authenticate
for local delivery or relay.
So it does what you are looking for.
Jeff
Well, goddarn it - so it does!
I was testing various permutation (10.3.4) just recently and it just wouldn't relay without auth if any of them was selected (honest!). That was with the trusted relay....
...but I just tried it again and it's fine!
I had put it down to just another 'glitch' in the documentation.
Oh well - glad you were there to point it out Jeff!
Whilst we are on the subject - do you know of any way to tie authentication (outwith trusted network) to specified users? I was thinking there might be a Postfix parameter for this (sorry, I should just look them all up but maybe someone knows it already)?
Thank, and sorry for any earlier confusion!
-david.

Smtp auth required

Hi
As of today I am getting an alert for thunderbird saying. The mail server responded: SMTP Auth required for message submission on port 587.
Can anyone tell me how I fix this. My tech guys say there should be a tick box in thunderbird saying the server requires SMTP Authorisation but I can't find it anywhere.

''christ1 [[#answer-700312|said]]''
<blockquote>
Tools (Alt-T) - Account Settings
Select 'Outgoing Server (SMTP)' in the left pane, it's at the bottom of the pane.
Select your SMTP server - Edit
Enter your user ID.
Thunderbird will prompt you for a password the next time you attempt to send a message.
</blockquote>
Hi Chris
We have tried changing the password but this does not solve the problem.
I am looking for a tick box that say SMTP requires authorisation.
Thanks

Mail and SMTP auth (RFC 1918 error) ?

I've an iMac and a Macbook (both with Mac OS X 10.5.3). Both connected to Internet using Airport via my WiFi router (with NAT activated on this router). This behavior is working fine since almost 2 years.
I was using (and I'm still using) Thunderbird (last version) to read and send my emails on the iMac, and Mac OS X Mail on the Macbook.
Everything was fine until yesterday. My provider has change is SMTP server so that authentification is now required when sending message.
So I've activated SMTP auth in Thunderbird and all is fine. And do the same under Mail (with password option). But it doesn't work with Mail, I've got a SMTP connexion error.
When I choose the diagnostic button, I find that SMTP connexion (EHLO) is fine, then saying my IP address (192.168.x.x) is private according to RFC 1918 and ending the connexion (QUIT).
I have the same error on my iMac, though it just work fine with Thunderbird.
So it seems to me Mail can't connect because of this behavior. But I don't understand why my IP address in Mail dialog with my provider SMTP server is not NATed by my router, like all other IP traffic.
And I don't know what to do to correct this problem.

Well, as SMTP authentification is only required to forward mail to another domain, I try to send an mail to my wife who is on the same domain as myself. It work fine with authentification disabled using Thunderbird but don't work with Mail.
As it use to work fine until I change the configuration, I try to delete my account informations and create a new one as it was 2 days ago (without SMTP auth) but it still doesn't work even if I've got no problem with Thunderbird.
Anyone as an idea about all this mess ? My only clue is the Mail connection diag which show connect, helo (with my private IP), server response 550 RFC 1918 and quit. Even if I found this behavior very strange, the result of the diag is the same with or without SMTP auth actived. So I suppose it was already the same before when it was working fine...

Missing Property "mail.smtp.auth" in JavaMail Spec Appendix A

Hi folks,
I tried to connect to my Mail Server via JavaMail over SMTP in oder to send an Email. The Mail Server needs Authentication. I always got the warning: 530 Authorization required, even though I had set my username and Passwort in my javax.mail.Transport object. I took a look into the Spec and there was no property like "mail.smtp.auth". In the FAQ I found it, recently.
I don't know if this should be reported as a bug. Perhaps somoene who is involved in the documentation writing reads this and changes this little fault.
Thanks,
Greets Juan.

Hi Juan,
take a look at the API doc -> package com.sun.mail.smtp.. here ou can find the properties.
Appendix A is old.
greetings,
Filo

AuthenticationFailedException when using JNDI and JavaMail with SMTP auth

Hi all - I've been banging my head on this one for awhile now - hopefully someone else has done this.
We are working in a servlet container (tomcat), and need obtain a mail session from JNDI. We do this as follows:
               Context initCtx = new InitialContext();
               Context envCtx = (Context) initCtx.lookup("java:comp/env");
               Session mailSession=(Session) envCtx.lookup("mailSession/trumpetinc");so far so good. The jndi entry for the mail session is configured in server.xml as follows:
          <Resource name="mailSession/trumpetinc" scope="Shareable" type="javax.mail.Session"/>
          <ResourceParams name="mailSession/trumpetinc">
            <parameter>
              <name>mail.smtp.host</name>
              <value>mail.server.com</value>
            </parameter>
            <parameter>
              <name>mail.smtp.password</name>
              <value>ABCDEFG</value>
            </parameter>
            <parameter>
              <name>mail.smtp.user</name>
              <value>trumpet_kevin</value>
            </parameter>
         <parameter>
           <name>mail.smtp.auth</name>
           <value>true</value>
         </parameter>
          </ResourceParams>With the above, whenever we hit Transport.send(msg), we got an AuthenticationFailedException thrown. I have run into this before with SMTP authentication, so I decided to try using the transport.sendMessage() method instead.
So, I get the transport:
Transport trans = mailSession.getTransport("smtp");
trans.connect();Then I send my message using:
msg.saveChanges();
trans.sendMessage(msg, msg.getAllRecipients());and finally, I close the transport:
trans.close();Unfortunately, I'm still getting the exception. Is it possible that my connect() method is not picking up the JNDI properties set in the server.xml file (this seems likely)? If so, what's the best way for me to get those properties so I can set them explicitly in the connect() method?
Thanks in advance,
- Kevin

Hi,
I have faced the same problem and after some googling and trying I have discovered what causes the AuthenticationFailedException exception. I just wanted to share the knowedge maybe it will be helpfull to others.
Here it is what the API says:
To use SMTP authentication you'll need to set the mail.smtp.auth property (see below) and provide the SMTP Transport with a username and password when connecting to the SMTP server. You can do this using one of the following approaches:
1.Provide an Authenticator object when creating your mail Session and provide the username and password information during the Authenticator callback.
Note that the mail.smtp.user property can be set to provide a default username for the callback, but the password will still need to be supplied explicitly.
This approach allows you to use the static Transport send method to send messages.
2.Call the Transport connect method explicitly with username and password arguments.
This approach requires you to explicitly manage a Transport object and use the Transport sendMessage method to send the message. The transport.java demo program demonstrates how to manage a Transport object. The following is roughly equivalent to the static Transport send method, but supplies the needed username and password:
Using the Transport.connect makes the JNDI not very helpfull for configuration.
It seems that using just the mail.smtp.user and mail.smtp.pass is not sufficient for the authentication.
so, the solution is :
just place these to lines in the JNDI configuration:
          username="test"
          password="test1"
so it should looks as follows:
          <Resource name="mail/Session" auth="Container"
          type="javax.mail.Session"
          username="test"
          password="test1"
          mail.transport.protocol="smtp"
          mail.smtp.auth="true"
          mail.smtp.host="localhost"
          mail.smtp.port="25"
          mail.smtp.user="test"
          mail.smtp.password="test1"
/>
where test and test1 are the user's credentials
Regards,
Kiril
Message was edited by:
Kireto
Message was edited by:
Kireto

I need a mail server without SMTP authentification. Which is the right one? Or how to configure OSX Lions Mailserver?

Hello folks,
our HP Scanner with email delivery is one the most used pieces of hardware in our office. Just scan and get delivered to your inbox. That works easy and perfect.
Unfortunately we had to change our standard mail server and now a prerequsisite is the smtp authentification. But the HP admin interface on the scanner does not allow to enter smtp auth credentials. It only supports smtp delivery without username/password. Now I have a serious problem. I cannot find any external provider that supports smtp mail delivery without smtp authentification (against spam of course, I understand that).
I have a OSX Lion Server running as a file server in our network. But I have no clue if there's a way to use it's mailserver without smtp auth.
Is there anyone who can help me out?
Cheers,
Joo-Chen

I have a OSX Lion Server running as a file server in our network. But I have no clue if there's a way to use it's mailserver without smtp auth.
Sure. Turn it on.
The default mode is to not require authentication. You have to turn on authentication if you want it.
Changing authentication on/off is a matter of clicking a radio button.

SMTP-auth via mailx results in service unavailable

Why do my attempts to use mailx with Gandi SMTP fail with 'Service unavailable'?
I have the following ~/.mailrc file which is recognised by mailx:
set smtp=smtps://mail.gandi.net:465
set smtp-auth=login
set smtp-auth-user=harry@XXXXXXX
set smtp-auth-password=XXXXXXX
set from=harry@XXXXXXX
set ssl-verify=ignore
set nss-config-dir=/Users/neville/Thunderbird
The result is below.
From MAILER-DAEMON Thu Dec 20 15:41:47 2012
Return-Path: <>
X-Original-To: [email protected]
Delivered-To: [email protected]
Received: by G4-N-2.local (Postfix)
          id D4E2DA382D6; Thu, 20 Dec 2012 15:41:47 +0000 (GMT)
Date: Thu, 20 Dec 2012 15:41:47 +0000 (GMT)
From: [email protected] (Mail Delivery System)
Subject: Undelivered Mail Returned to Sender
To: [email protected]
Auto-Submitted: auto-replied
MIME-Version: 1.0
Content-Type: multipart/report; report-type=delivery-status;
          boundary="78E73A382D4.1356018107/G4-N-2.local"
Message-Id: <[email protected]>
This is a MIME-encapsulated message.
--78E73A382D4.1356018107/G4-N-2.local
Content-Description: Notification
Content-Type: text/plain; charset=us-ascii
This is the mail system at host G4-N-2.local.
I'm sorry to have to inform you that your message could not
be delivered to one or more recipients. It's attached below.
For further assistance, please send mail to postmaster.
If you do so, please include this problem report. You can
delete your own text from the attached returned message.
                   The mail system
<neville@XXXXXXX>: host spool.mail.gandi.net[217.70.184.6] said: 554 5.7.1
    Service unavailable; Client host [XXXXXXX] blocked using
    pbl.spamhaus.org; http://www.spamhaus.org/query/bl?ip=XXXXXXX (in
    reply to RCPT TO command)
--78E73A382D4.1356018107/G4-N-2.local
Content-Description: Delivery report
Content-Type: message/delivery-status
Reporting-MTA: dns; G4-N-2.local
X-Postfix-Queue-ID: 78E73A382D4
X-Postfix-Sender: rfc822; [email protected]
Arrival-Date: Thu, 20 Dec 2012 15:41:47 +0000 (GMT)
Final-Recipient: rfc822; neville@XXXXXXX
Action: failed
Status: 5.7.1
Remote-MTA: dns; spool.mail.gandi.net
Diagnostic-Code: smtp; 554 5.7.1 Service unavailable; Client host
    [XXXXXXX] blocked using pbl.spamhaus.org;
    http://www.spamhaus.org/query/bl?ip=XXXXXXX
--78E73A382D4.1356018107/G4-N-2.local
Content-Description: Undelivered Message
Content-Type: message/rfc822
Received: by G4-N-2.local (Postfix, from userid 501)
          id 78E73A382D4; Thu, 20 Dec 2012 15:41:47 +0000 (GMT)
To: neville@XXXXXXX
Subject: test
Message-Id: <[email protected]>
Date: Thu, 20 Dec 2012 15:41:47 +0000 (GMT)
From: [email protected] (Neville Hillyer)
test email
--78E73A382D4.1356018107/G4-N-2.local--

http://www.spamhaus.org says:
Mail servers only run spam filters such as Spamhaus PBL on port 25, so if you find you are being blocked by the PBL when you try to send mail to your mail server that means you are not communicating with the mail server on the 'authenticated' port 587 but you're still on port 25. This means your 'SMTP Authentication' is not working correctly.
http://wiki.gandi.net/en/mail/standard-settings#smtp-account says:
SMTP Account
Name server : mail.gandi.net
Port : 25, 465 (with SSL) or 587 (try one or the other)
TLS or SSL: yes
SMTP Authentication : yes, using the same settings as for the POP / IMAP account
I was trying to use the same settings I have used for several years with Thunderbird and Apple Mail, ie SSL on port 465.
Is there something wrong with my settings which could be preventing mailx from using port 465?
A few debug tips would be appreciated.
Your link causes me to ask: Does the mailx on Leopard support SMTP directly?

How to add X-authenticated header with SMTP-auth

I have smtp-auth working here. I also have normal mail header to see what ip the message is coming from. But I'd like to add X-authenticated to signature the mail is authenticated by end user.
Can I do that? What parameter i can use for message filter?
Many thanks.
Chris

Currently you can't ; however, you should open a case with IronPort and request that feature - the more that request the feature the better the chance for it to get implemented. My company has already requested this feature. We asked for a variable and a condition that we could use in filters.

Pop before smtp and smtp auth

Hi Jay,
hope all is well with you.
what is pop before smtp and how to see if it is enabled?
what is smtp auth and how to see if it is enabled? Is it enabled by default on MS 6.x?
what happens if smtp auth is not enabled? Will my mail server be a relay?
Is there any additional configuration that should be done on messaging server to allow connection for dial-up users?
thanks,

Hi Jay,
hope all is well with you.
what is pop before smtp and how to see if it is
enabled?Pop before SMTP is a very old, and little used method for "authenticating" users. There is virtually no reason to turn this on, anymore.
It's done through the MMP, and is the only reason to actually use the SMTP proxy that's part of MMP.
I would not go there unless your environment requires it. Most do not. Most clients support SMTP authentication, which is much better, and is on by default.
>
what is smtp auth and how to see if it is enabled? Is
it enabled by default on MS 6.x?See above. Yes, smtp authentication is on by default.
>
what happens if smtp auth is not enabled? Will my
mail server be a relay?Totally different issue.
No.
If smtp auth is off, if you have external users, they likely will not be allowed to send to other external users..
>
Is there any additional configuration that should be
done on messaging server to allow connection for
dial-up users?If "dial-up users" means that they come from ip addresses outside your network, then smtp auth will allow them full access.
thanks,

Server to server smtp auth

Hello,
I have a Messaging 6.x (JES 2005Q4 version) installation. All outbound email must go
through an external MTA so I added a smartrelay (daemon in tcp_local channel) and all works ok but the external MTA requires authentication so the question is:
how can I configure to send SMTP AUTH to the smartrelay?
I get the following when sending mail:
27-Jan-2006 18:42:00.44 tcp_local R 1 [email protected] rfc822;[email protected] [email protected] dns;outbound.relay.com (outbound.relay.com ESMTP Exim 4.51 Fri, 27 Jan 2006 19:41:57 -0500) smtp;550 You must authenticate to use this relay
I have set this up in a postfix installation and all works ok.
Thanks all in advance.

Hello,
I have a Messaging 6.x (JES 2005Q4 version)
installation. All outbound email must go
through an external MTA so I added a smartrelay
(daemon in tcp_local channel) and all works ok but
the external MTA requires authentication so the
question is:
how can I configure to send SMTP AUTH to the
smartrelay?Far as I know, you can't.
>
I get the following when sending mail:
27-Jan-2006 18:42:00.44 tcp_local R 1
[email protected] rfc822;[email protected]
[email protected] dns;outbound.relay.com
(outbound.relay.com ESMTP Exim 4.51 Fri, 27 Jan 2006
19:41:57 -0500) smtp;550 You must authenticate to use
this relay
I have set this up in a postfix installation and all
works ok.
Thanks all in advance.

DIsable smtp auth only for an ip

Dear gurus,
I have sun messaging server 6 running perfectly alright and only new thing which I would like to incorporate is to disable smtp auth only for one ip address.I am new to this system and have gathered following information from sun messaging docs, the steps which I followed..
1) Create a table DISABLE_SMTPAUTH_IP similar to INTERNAL_IP mapping table in mapping file
INTERNAL_IP
10.18.18.19 $Y
10.18.18.38 $Y
10.18.18.30 $Y
127.0.0.1 $Y
* $N
! Added on 01092008 for disabling smtp_auth
DISABLE_SMTPAUTH_IP
external.ip.addres $Y
*$N
2) ALLOW PORT ACCESS
*PORT_ACCESS
*|*|*|*|* $C$|DISABLE_SMTPAUTH_IP;$3|$Y$E
*|*|*|*|* $C$|INTERNAL_IP;$3|$Y$E
3) Then right after the current rewrite rule in imta.cnf file Created new TCP CHANNEL
! Do mapping lookup for internal IP addresses
[] $E$R${INTERNAL_IP,$L}$U%[$L]@tcp_intranet-daemon
added a new rewrite rule:
! Do mapping lookup for "no smtp auth", non-internal IP addresses
[] $E$R${DISABLE_SMTPAUTH_IP,$L}$U%[$L]@tcp_nosmtpauth-daemon
! ttcp_nosmtpauth-daemon
tcp_nosmtpauth-daemon smtp mx single_sys subdirs 20 maxjobs 7 pool SMTP_POOL nosasl nosaslserver
tcp_nosmtpauth-daemon
! tcp_local
tcp_local smtp mx single_sys remotehost inner switchchannel subdirs 20 maxjobs 30 pool SMTP_POOL maytlsserver maysaslserver s
aslswitchchannel tcp_auth loopcheck threaddepth 32 blocklimit 5120 notices 1 2 backoff "pt5m" "pt1h" "pt2h" "pt4h" destinati
onspamfilter1optin spam
tcp-daemon mumbbmr1.dataone.in
! tcp_intranet
!tcp_intranet smtp mx single_sys subdirs 20 dequeue_removeroute maxjobs 7 pool SMTP_POOL maytlsserver allowswitchchannel sasl
switchchannel tcp_auth blocklimit 2500
!tcp_intranet smtp mx single_sys subdirs 20 dequeue_removeroute maxjobs 7 pool SMTP_POOL maytlsserver allowswitchchannel sasl
switchchannel
!tcp_intranet-daemon
run /opt/SUNWmsgr/sbin/imsimta refresh
alternatively tried imsimta cnbuild and imsimta restart
but still i get Mail rely denied when I try sending messages from the same trusted IP without doing AUTH.
I would like to know...
1) If there is something mising or wrong in above steps
2) HOw do i check if the messages from that IP(for which smtp auth is disabled) is passing from the tcp_nosmtpauth channel...
THanks for giving your valuable time...

thanks very much shane for giving time...
Please always provide the exact version of Messaging Server (./imsimta version).
mumxxxx1 # ./imsimta version
Sun Java(tm) System Messaging Server 6.2-6.01 (built Apr 3 2006)
libimta.so 6.2-6.01 (built 11:20:35, Apr 3 2006)
SunOS mumxxxx1-a-fixed 5.9 Generic_118558-28 sun4u sparc SUNW,Sun-Fire-V440
mumxxxx1#
Why would you want to disable SMTP Authentication? What are you attempting to achieve by doing this -- what is the problem you are trying to solve?
We are an ISP and therefore sometimes required to send bulk mail, for which we are currently using perl bulk mail module script and there we specify the users in text file to send message, everytime this module try sending it get Mail Relaying denied as it doesnot supply user and passwd required for smtp auth in base64.
Therefore I wanted to disable smtp auth for an ip address using which smtp auth is not reqauired and mails should be openly relayed.
Why are all of the above entries commented out? Did you intend to disable (break) the tcp_intranet channel?
no it is not commented in config files.
+./imsimta refresh is no longer a valid comment, you need to use ./imsimta cnbuild;./imsimta restart+
as per sun mesaging server 6 admin guide it is given to be working. Alterntively I tried ./imsimta cnbuild;./imsimta restart.
Please provide the mail.log_current line that matches the attempted email delivery which was rejected.
mumxxxx /opt/SUNWmsgsr/sbin # tail -f /mta/logs/imta/mail.log_current
08-Sep-2008 13:42:19.52 7079.0fca.710096 tcp_local J 0 [email protected] rfc822; [email protected] mailserv 530 5.7.1 Relaying not allowed: [email protected] SMTP
bash-3.00# telnet mumxxxx 25 Trying 10.18.18.19...
Connected to ::ffff:10.18.18.19.
Escape character is '^]'.
220 mumxxxx.datxxxx.in -- Server ESMTP (*)
ehlo mumxxxx.daxxxx.in
250-mumxxxx.daxxxxx.in
250-8BITMIME
250-PIPELINING
250-DSN
250-ENHANCEDSTATUSCODES
250-HELP
250-XLOOP 82F58AB6E3453199924062C516F2E337
250-AUTH PLAIN LOGIN
250-AUTH=LOGIN
250-ETRN
250-NO-SOLICITING
250 SIZE 0
mail from: [email protected]
250 2.5.0 Address Ok.
rcpt to: [email protected]
530 5.7.1 Relaying not allowed: [email protected]
rcpt to: [email protected]
Also please clarify if you want to disable the ability to perform SMTP auth or whether you want to allow email to be sent without requiring SMTP auth -- these are two completely different objectives.
No I do not want to disable SMTP auth for everyone.DEfault is it should be forced to all except from one ip. ie disable smtp auth only for an ip address.
Regards
Pradeep

Difficulty sending mail to secure SMTP, SMTPAddressFailedException: 554

I keep getting the following exception in my application:
class com.sun.mail.smtp.SMTPAddressFailedException: 554 <[email protected]>: Recipient address rejected: Relay access denied
My code is as follows:
public class SMTPSender {
     private Session session;
     public SMTPSender() {
          Properties props = new Properties();
          props.setProperty("mail.smtp.host", AutomailingUtility.HOST);
          props.put("mail.smtps.auth", AutomailingUtility.AUTH);
          props.put("mail.smtp.port", "465");
          props.put("mail.smtp.socketFactory.port", "465");
          props.put("mail.smtp.socketFactory.class", "javax.net.ssl.SSLSocketFactory");
          props.put("mail.smtp.socketFactory.fallback", "false");
          Authenticator auth = new MyAuthenticator(AutomailingUtility.USERNAME, AutomailingUtility.PASSWORD);
          session = Session.getInstance(props, auth);
     public void sendMessage(String toUser, String message, String subject) {
          try {
               Message msg = new MimeMessage(session);
               msg.setSubject(subject);
               msg.setSentDate(new Date());
               InternetAddress ia = new InternetAddress(AutomailingUtility.FROM_ADDRESS);
               msg.setFrom(ia);
               msg.setRecipients(Message.RecipientType.TO, InternetAddress.parse(toUser + "@mail.gatech.edu"));
               msg.setText(message);
               Transport.send(msg);
          } catch (AddressException e) {
               e.printStackTrace();
          } catch (MessagingException e) {
               e.printStackTrace();
}All the Automailing constants are strings.
I'd appreciate the help

The code? For regular SMTP with authentication I believe you needprops.put("mail.smtp.auth", "true");whereas you set up the mail.smtps.auth property instead. However I don't have any experience with secure SMTP, so I don't know what's right in that case. Are those other applications you mention using secure SMTP or just regular SMTP?

External SMTP Auth

Hi folks.
My iPod is not happy. She (he?) can't send mail from outside. I have an IMAP account that I use on my LAN server for my domains. When I go out, I can't send mail.
Now, port 465 is apparently used for SSL SMTP, but that isn't open on the server. My router has SMTP Mail open.
What I want to do, I forget the name of. I think it's SMTP Auth, and using a port above what routers would normally close off. So I'd like to use port 3500 or something like that. How do I do that, while using Kerberos or MD5 for sending mail from outside?
Cheers

I'd confirm that your ISP is (or is not) blocking inbound port 25; if the server here is connected into the ISP via a residential-grade service tier, then port 25 and port 80 blocks in-bound are fairly common. That is, confirm whether the connectivity problems here are between the ISP and the server, or at the pub.
As for your own network perimeter, most consumer-grade routers are pretty weak, while those router-firewalls with VPN and port-forwarding aren't that much more expensive. And there are open-source firewalls around. And using a VPN into the firewall is a pretty good solution for many reasons.
Various organizations that offer wireless do block port 25 outbound and sometimes other specific outbound ports to reduce the spread of malware, or the network loading that can result from torrents. Few organizations block outbound VPNs or webmail (port 80 or port 443) connections.

SMTP Auth & Maildir

I have two seperate questions...
I found this quote here:
http://docs.info.apple.com/article.html?artnum=106763
"Whenever Authenticated SMTP is enabled, your email server is effectively a "send only" server, because mail servers from other domains are most likely not configured to authenticate with your server. This means your local email clients can only receive email from other local clients. Authenticated SMTP also requires each user's email client software to authenticate before it sends mail through your server."
I know this documentation is very old (10.1.3), but I need to know if this still true in Server 10.4.7? I have a LOT of traveling sales people that need to use either mail.app or outlook, and they are not going to be happy if I tell them they have to use webmail. I was planning on switching to OS X Server, but I need to know about this first.
My second question is, what format does 10.4.7 server store its mail in? mbox? mdir? I have found conflicting answers online..
Thanks,
Brian
Macbook Mac OS X (10.4.7)

Actually, that excerpt does not make sense to me either.
When Authenticated SMTP is enabled, only clients with the correct username and password may relay mail through your server. Any other client or server will not be able to relay mail through your server. The only mail your server will accept without authentication is those that are meant for the local accounts on the server. SMTP-AUTH just prevents unauthorized relays but not delivery.
So your travelling reps should be able to use Mail.app to connect to your server and send mail to outside clients through your server. AND their clients should be able to send mail to your reps.

Mail 2.0 + SMTP auth + qmail

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