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SMTP Authentication Help Please

Hi everyone,
I am having a problem. We are running an Exchange 2007 server behind an IronPort mail security appliance. Standard mail receipt and delivery are working wonderfully. We recently had a request to enable IMAP and SMTP access from the outside world, which has always in the past been forbidden. We have secure IMAP working just fine, but we are having problems with SMTP so these IMAP users can send mail.

I have setup the IronPort so users can connect to it, and then it passes the connection back to the mail server for authentication. I see the traffic coming from the IronPort and getting to the mail server, but the mail server is not doing Authentication. The IronPort is sending me a message, stating that no available AUTH methods are implemented. On the receive connector, i have Integrated Windows Authentication, Exchange Server Authentication, Basic (including TLS) and TLS (DOmain Security Mutual TLS) enabled.

When i try and telnet to this server to test, i am seeing the following:

250-SIZE
250-PIPELINING
250-DSN
250-ENHANCEDSTATUSCODES
250-X-ANONYMOUSTLS
250-AUTH NTLM-------------------< Shouldn't this be AUTH LOGIN?
250-X-EXPS GSSAPI NTLM
250-8BITMIME
250-BINARYMIME
250-CHUNKING
250-XEXCH50
250 XRDST

How do i change it to AUTH LOGIN, not AUTH NTLM?

Any assistance would be greatly appreciated. I have people breathing down my neck to get this working.

Thanks in advance

app


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Hello, we are running Exchange 2003 SP2 on a Windows 2003 SP1 box.  One of my users emailed a company and she got a bounce back message saying: smtp;550-Not authenticated, please enable SMTP authentication in email software and check credentials.

What does this mean?  Doesn't Exchange 2003 do smtp authentication by default?  She is able to send emails to a different email address at the same company, so as of right now I am assuming the problem is on their end?  Any help would be greatly appreciated!

David

Hey, I'm a newbie, so please be gentle!

I have an issue with SBS Exchange 2003 SMTP authentication. I have a domain and email hosted by 1&1, ISP is BT. I have no problem with downloading emails using the POP3 connector built-in, it is the SMTP connector security settings that I am unsure of as I am unable to send any external emails. I get bounceback messages saying that SMTP must be authenticated.

I have read numerous articles about smart hosts, relaying, etc but none have helped. Have tried changing port from 25 to 587 and nothing has happened. Spoken to 1&1 and "they won't assist me with my Exchange configuration".

Any help anyone would be able to give me would be much appreciated.

Pete

This error message was received when Outlook bounced back an email I sent,
it would be nice if they told me what SMTP Authenticate means and how to do
it.

Help please... Bob

*********************************************

The reasons given by the server are included to help you determine why each
recipient was rejected.

Recipient:

Reason: You must SMTP Authenticate before sending to staff@thetrophyshop.com

Hi,

hope somebody can help me please. Have Outlook Express 6 on a XP machine and
need to use SMTP authentication for sending out emails. Works fine when
entered and when restarting Outlook Express, but on computer restart, the
setting default back to using POP3 settings. In general the machine is
resetting my STMP setting on restart, can anybody help please.

many thanks
Simon

This error message was received when Outlook bounced back an email I sent,
it would be nice if they told me what SMTP Authenticate means and how to do
it.

Help please... Bob

*********************************************

The reasons given by the server are included to help you determine why each
recipient was rejected.

Recipient:

Reason: You must SMTP Authenticate before sending to

I have an add-on package to my Manufacturing ERP system that allows you to click on a button and send information in the system via an email.  Apparently it does not use the user's outlook to do this, but SMTP.  I have Exchange 2003. 

When my users send the email to an outside email address they get the following error message: SMTP service error, impromper (sic) response code.  Code should have been: 250 Code recieved (sic): 550.5.7.1 Unable to relay for email@mailbox.com Error Description: Requested action not taken: mailbox unavailable  Addiitional Information: RCPT TO: email@mailbox.com Timer Exceeded?  True [OK].

The vendor tells me that I need to setup SMTP Authentication or open an SMTP relay.  I have no idea what that means.  I cannot find any articles or chapters in my books on setting up SMTP Authentication.

Anyone have any ideas, links to articles that will help me get this setup?

Hello,I have Exchange 2000 on Windows 2000 (SP1) with SMTP Connector. My users remotely access my exchange server using dial-up connection to the Internet (Outlook Express).
I want to restrict access only to the users who successfully authenticate. I have removed "anonymous access" and enable "Basic Authentication" on the properties of Default Virtual SMTP Server" which results in that nobody can send message to any of my server's user. Any help? How can I enable SMTP Authentication because my remote users always connect with different (dial-up) IPs and I cannot use IP or Domain based Access
List.In exchange 5.5 I use to do so without any problem by selecting "Hosts and Clients that successfully authenticate" under Routing Restrictions in IMS properties.

We just completed an Exch5.5 to Exch2K3 migration.
I have an SMTP Queue now named "Deleted Objects" and it has a bunch of messages we need sent/received.

What is this queue? and furthermore how to I get those messages to be received by the correct party?

Help Please and Thanks ahead of time for those that can help.

Hi Folks

I will try to keep this problem explaination as short as possible but as we are novice exchange administrators I hop we dont miss something out.

OK just to give you some background on our clients system.

Server os: small business server 2000
clients using mixture of outlook 2000 and 2002

from what I remember from when I first configured the exchange server I configured the small business smtp connector to forward all mail to a smart host, this being mail.btopenworld.com - i think this is all I configured and all clients were able to send email no problem.

Since yesterday a couple (bt have confirmed they have made a change on their smtp servers in that they now require authentication)and I emphasise only a couple of clients have started to have trouble sending email. They are recieving a bounce back saying something about requiring smtp authentication. The bounce back states that you should go into outlook and tick the box that says "my smtp server requires authentication" this option however is not available when outlook is configured to use exchange server.

The strange thing is if I configure the clients outlook with a normal pop3 account and using mail.btopenworld.com as the smtp server and NOT checking the box for "my smtp server requires authenticatiion" the email still sends without any problem therefore I am deducting that I need to change a setting and exchange server but this does not explain why it is only happening with a couple of users.

I won't post anymore information that this at the moment in case I am not explaining the situation more clearly however if anyone can help I will give you more information if is needed.

Thanks for any help

I have exchange server installed on a windows 2003 server machine. Verio
does my email and web hosting. I am a small business with no IT department
and the person who helped set up my server has moved.

Just recently I started having mail I was sending to AOL returned back to
me. I called AOL with the error code and AOL said they no longer are
accepting email sent through port 25. It appears I need to now use port
587. I need for someone to point me to a detailed step by step (and I mean
step by step) description of how I change the smtp port for my smtp server.
When I go to the pop mail connector in windows it looks like I get only pop
settings.

Thanks in advance for any help you can give me.

I have a SBS 2003 server running exchange, and a mail server provided by an ISP. everything was fine until the ISP enabled SMTP authentication on the mail server. Now I can only receive mail, sending mail gives me "550 SMTP authentication error". I have checked all my settings on exchange but cannot overcome this problem.

Any help will be greatly appreciated.....

Hi all

I have some users who are using outlook 2007 in a different network.. So they are using the real IP's... but when configuring the SMTP authentication, the messages won't go... if they disable it they will be able to send messages... and this makes our mail content filtering server to consider their messages as spam as they are not using the SMTP authentication.... I tried to configure the MS outlook2003 with th SMTP authentication, they will be able to send messages with no errors.. I was wondering what is the problem here... btw, my Exchange is 2007...

any one can provide help

Thanks in advance.

Two days ago my Outlook 2007 stopped sending mail on 3 of my email accounts.
I have 7 in total and the others work fine. I can also receive mail no
problem. I've been searching for an answer on various forums, but no luck.
Before the problem, everything was working fine. I made no hardware or
software changes, except that I moved from a wireless network to a hardwired
LAN. I think the problem is in the SSL encryption, as the 3 problem accounts
require SMTP authentication, and 2 of the 3 require an encrypted (SSL)
connection on the default port 25 (SMTP) and 110 (POP3). System info: Intel
Pentium 4 3.2G, 2G RAM, Windows XP Pro SP2 with all updates installed, Office
2007 Pro with all updates installed. 2 of the 3 email accounts are hosted
with a UK ISP, and the other is hosted with a German ISP. Both ISP plead
innocent. The net connection is provided by a 3rd ISP, and they have also
checked it out and said everything is fine on their side. I have done all the
usual: deleted and recreated the accounts, restarted the PC, removed
authentication, changed encryption method to auto and TLS and any combination
of the above. I run Tren Micro PC Cillin 2007, and Outlook is on the allowed
program list, and port 25 is enabled to send data on. Nevertheless I have
completed turned off the anti virus, with the same result. I get one of two
error messages: either 0x8004210B (server time-out). I increase the server
timeout to the max allowed (10 minutes) but this does not help. The other
error message I get (depending on how I fiddled with the account set-up) is
0x800CCC1A (which usually means the server does not requre SSL but it has
been enabled) but as mentioned, I had tried it both ways, and the ISP tells
me that it DOES require SSL in any event. On very rate occasions (I'd say
once in every 100 attempts) I managed to send out an email so it DOES work,
but this is only very seldom, and obviously not helping much. It seems as
though the SMTP is experiencing some sort of block or interference, and it
simply cannot get the data sent through. ANY advice or help would be greatly
appreciated!

I have been using Outlook 2003 for ages to access my BtInternet mail,
and now all of a sudden i am being asked to confirm my network password

over and over, and regardless it still will not send my mail.

I can recieve mail fine but not send...

I have been on to Yahoo and it sends ok.

I have removed the account and reset it.

I have checked and confirmed the settings about a million times :-).

But it is still asking me.

I have a feeling it is a problem with the program (or been hit with a
virus of some kind), I did uninstal it and re-instaled, but there must
be some settings it does not remove fully because when i re-installed
my history was still there....

I have changed my password on line and still no good..

when i test the account I get told ' Send test email message: outlook
could not connect to the out going SMTP mail server did not accept your
user name or password'

help please.......

Hi, I would like to know how to set SMTP Authentication Setting on MS Outlook
2002 SP3./WindowsXP-Home with the latest MS Updates.
When on E-MAIL ACCOUNTS at Internet E-mail settings (POP3) instead of
SETTINGS my version shows TEST ACCOUNT SETTINGS-NEXT-FINISH. Where else can I
set E-mail settings?
Help appreciated.
Pedro

I have been using Outlook 2003 for ages to access my BtInternet mail,
and now all of a sudden i am being asked to confirm my network password

over and over, and regardless it still will not send my mail.

I can recieve mail fine but not send...

I have been on to Yahoo and it sends ok.

I have removed the account and reset it.

I have checked and confirmed the settings about a million times :-).

But it is still asking me.

I have a feeling it is a problem with the program (or been hit with a
virus of some kind), I did uninstal it and re-instaled, but there must
be some settings it does not remove fully because when i re-installed
my history was still there....

I have changed my password on line and still no good..

when i test the account I get told ' Send test email message: outlook
could not connect to the out going SMTP mail server did not accept your
user name or password'

help please.......

Same settings for outlook 2007, there is no problem to send email. But Outlook 2010 keep asking username and password for outlook 2010.   Also use the same authentication method, there is no problem for outlook 2010 to send email via yahoo mail.  Definitely there is something about outlook 2010 and exchange server 2010 SMTP authentication. No Antivirus software and windows 7 ultimate 64bit.  Someone can help? Thank youPangsha Qiu

Hi all. I'm trying to get some SMTP authentication issues ironed out and I've discovered some things that didn't seem quite right to me.

I have quite a few users that travel. While they are on the road I have them pulling their mail via pop3 and using our SMTP to send. I would have them just use OWA but they complained enough and I was overruled. So while working on a users outlook settings the other day I noticed some "strange" behaviour from the SMTP for these off-site users.

I have all these off-site users set to authenticate with the SMTP server and to use the same credentials they are using for pop3. Everything works fine. Here's where things get strange...

1. If I uncheck the option to Authenticate with the SMTP server, I get a relay restriction error. This IS expected.

2. If I have the SMTP authentication option checked and I have it set to use their POP3 credentials (or manually giving their UN/PW) BUT I have their email client configured with an invalid email address (one that doesn't exist on our server), the mail refuses to send and I get a relay error.

3. If I have the mail client configured with the correct email address but I also set the SMTP authentication by manually specifying the Un/PW, it does not matter what UN/PW I enter, the mail will still send successfully. Basically I can enter any UN/PW, whether that account actually exists on our domain or not, and the mail will still relay.

Is this by design? This seems like a pretty serious security flaw to me.

Just for the record I have my relay restrictions set to allow only the ones listed (none listed) and to allow all authenticated users to relay mail.

So again, is this some security flaw or have I screwed something up? Or is there another explanation for all this that I am overlooking? Thanks!

Dear Friends

I am using pop3 connector to download email and sent to exchange 2003. my outbound email required smtp authentication before it is accepted by my email domain mail.mycompany.com. I knew how enable outbound smtp authentication. but in my situation i need a unique smtp authentication for that email. for example email from support@mycompany.com should be authenticated with its username/pass, email from sales@mycompany.com should be authenticated with its username/pass. How can i add all these mutliple authentication in exchange outbound security. OR is there a way around

regards

shoeb

We have a request from a client vendor to make an account that allows for Basic SMTP authentication so that they can route mail through it. I have never had to make one for a client before so I was wondering what do I need to do with Exchange to do this.

Thanks!

We are using an external SMTP server to send email but, first it authenticates with the exchange server. However, since upgrading to exchange 2003 the pop3 client setting for outgoing smtp authentication has to enter in domain/username in order to authenticate. Where can I set a default domain in exchange 2003 so the pop3 client doesn't need domain/username.

How do I setup Exchange 2003 to require SMTP authentication to send email?

-Jeremy

I have exchange 2003 sp2 and running fine from inside I can connect fro workgroup computer can send and receive with pop3. But when I connect from external network it will give error 550 5.7.1 Unable to relayL . I try almost every thing from the client and the server. The only way that I open relay  “NO WAY”  Can Anybody help please.
Thanks
Mostafa

SMTP Relaying Help

I am trying to configure an exchange server to relay email, and it seems
that all I get in response is the following:

Action: failed

Status: 5.7.1

Diagnostic-Code: smtp;550 5.7.1 Unable to relay for user@domain.com

Can anyone help me with this.


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