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I have a small Exchange environment, 10 PCs running Outlook 2007, 3 Droid phones, 2 iPhones and a couple Ipod touches. I came in this morning to the realization that external recipients are not getting mail from us. There are no errors or kickbacks, the mail just disappears. Here's the weird part, the Apple devices connect via EAS, and are able to send no problem, recipient gets the message. The Android devices and all Outlook users (EXCEPT ONE!) are able to send, but the recipient never gets the mail, its like its sent to nowhere. OWA gives the same result as Outlook.

Message tracking in Exchange Console shows the messages going out.

My SMTP logs show exactly the same result for a message that wasn't delivered, as one that was by that one user that is able to send.

All mail to internal users works properly.

EDIT: There is only ONE user that can send, and this is through Outlook or OWA. To clarify,

User1 cannot send with Outlook or OWA, or his Droid using EAS to my gmail address, but can connect his iTouch to EAS and it sends fine.

User2 can send to my gmail account using Outlook, OWA (from any computer) or his iTouch. This is the ONLY user not experiencing any issues

I cannot send to my gmail account using Outlook or OWA, but my iPhone works using EAS

Here is the SMTP log of an undelivered mail:

Tue, 19 Oct 2010 13:40:38 -0400", EHLO mail.domain.com,

250-cm-omr9 says EHLO to our.external.ip.address:34152,

250-8BITMIME,

250-PIPELINING,

250-AUTH=CRAM-MD5 LOGIN PLAIN,

250-AUTH CRAM-MD5 LOGIN PLAIN,

250 ENHANCEDSTATUSCODES,

AUTH LOGIN,

235 Authed. Go on.,

63,sending message

MAIL FROM:User2@domain.com,

RCPT TO:me@gmail.com,

RCPT TO:User2@gmail.com,

250 MAIL FROM accepted,

250 RCPT TO accepted,

250 RCPT TO accepted,

DATA,

"354 continue. finished with ""\r\n.\r\n""",

250 OK 5C/1B-10393-618DDBC4,

QUIT,

221 cm-omr9 closing connection,

Here is the SMTP log of a delivered mail:

220 cm-omr4 ESMTP ecelerity 2.2.2.41 r(31179/31189) Tue, 19 Oct 2010 13:42:18 -0400",

EHLO mail.domain.com,

250-cm-omr4 says EHLO to mail.domain.com:5524,

250-PIPELINING,

250-ENHANCEDSTATUSCODES,

250-8BITMIME,

250-AUTH=CRAM-MD5 LOGIN PLAIN,

250 AUTH CRAM-MD5 LOGIN PLAIN,

AUTH LOGIN,

235 Authed. Go on.,

65,sending message

MAIL FROM

RCPT TO:me@gmail.com,

250 MAIL FROM accepted,

250 RCPT TO accepted,

DATA,

354 continue. finished with ""\r\n.\r\n""",

250 OK F9/15-07570-A78DDBC4,

QUIT,

221 cm-omr4 closing connection,

.220 cm-omr5 ESMTP ecelerity 2.2.2.41 r(31179/31189)

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So did you get the mail testing with telnet? –  Campo Oct 19 '10 at 18:49
    
OK, I did get a test via telnet! –  DanBig Oct 19 '10 at 19:02
    
OK so we know that everything is working correctly on the sending end. Try unmounting and remounting the mailbox store. Should jog EX2007 into working. Helps us sometimes. Do the users show CONNECTED TO EXCHANGE in outlook? –  Campo Oct 19 '10 at 19:19
    
I would think that rebooting the server would be the same as dismounting and remounting the store. All users show connected. –  DanBig Oct 19 '10 at 19:21
1  
Now that it's fixed, could you post a snippet of the log for comparison to the one in your original question? Also, is the new Send Connector configured exactly like the original, including the smart host? –  joeqwerty Oct 19 '10 at 20:16
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4 Answers 4

up vote 2 down vote accepted

Try creating a new smtp sendmail connector, make sure namespace is * and its internet based delivery. see if you can right click disable for the existing one after the new one is setup and then try delivery.

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I'd first suggest trying to send from OWA if the delivery works then at least this is a for sure way to bypass and client side issues and narrow it down to a server side problem.

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I've made some edits, OWA does not work. –  DanBig Oct 19 '10 at 17:16
1  
can the user send to themselves through owa ? user@domain.com emailing user@domain.com to see if they receive their own message. this can be important as it might help in why delivery is failing. –  Nick O'Neil Oct 19 '10 at 18:45
    
Good call @nicholas. +1 be interesting if they can't thats for sure! Though he said internal works –  Campo Oct 19 '10 at 18:50
    
We can communicate internally with no issues. –  DanBig Oct 19 '10 at 18:56
1  
the smtp send log shows the message went out, can you view the smtp mail queue from exchange administrator console, check all your smtp queues, i'm curious to know whats in there. In addition are any exchange services set to automatic currently stopped? –  Nick O'Neil Oct 19 '10 at 19:09
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Have you checked to make sure you are not on any block lists? mxtoolbox.com/SuperTool.aspx

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We are not..... –  DanBig Oct 19 '10 at 18:31
    
well thats a good sign. Have you tried to send mail via telnet to your gmail? Have you tried stopping and starting the mailbox store? Restart for SMTP server too? –  Campo Oct 19 '10 at 18:40
    
I've restarted the server several times, also, I applied SP3 for Ex2007, which had no effect. –  DanBig Oct 19 '10 at 18:49
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Are you forwarding your email to a smart host or spam filtering device or service that requires authentication, because that's what it looks like to me. My initial suggestion would be to remove the smart host and\or spam filtering device or service from your configuration, configure the server to use DNS to deliver email, and test again. If email is successfully delivered then you know the problem is the smart host and\or spam filtering device or service (which is my guess). If it doesn't work then you've narrowed the problem down to your server.

The log entries show that the email was delivered to and accepted by the servers\devices cm-omr9 and cm-omr4, so that's where the problem lies, from my perspective.

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is CM-OMR4 not the domain or server? its in the ESMTP banner.... –  Campo Oct 19 '10 at 19:34
    
I am using a smart host. Its through Network Solutions, always has been. It's always also been used without auth. I'm going to remove it and restart the services, and test. –  DanBig Oct 19 '10 at 19:34
    
It looks to me like cm-omr4 and cm-omr9 are the servers that the OP's server is connecting to and that those servers are accepting the messages from the OP's server. –  joeqwerty Oct 19 '10 at 19:47
    
Removed the SH, but still no delivery, it just ended making the SMTP log full of errors, and my iPhone wouldn't deliver. I've put the SH back in and my phone works again. –  DanBig Oct 19 '10 at 19:56
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