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Okay, once again I’m baffled with an issue that I’m hoping one of you can help me solve. Here’s the deal…

Configuration: Microsoft Office XP (Outlook 2003) on a Windows XP (SP3) system connected to a POP3 email host.

Sympton: Sending an email to anyone@mydomain.com works as expected. Sending email to another domain (MSN, HOTMAIL, GMAIL etc.) never arrives at its destination.

Why I’m Stumped (workflow):

  1. Email can be created with or without Word as my default email editor.

  2. Clicking Send/Receive produces the familiar “1 of 1 email being sent” and the process completes 100% without any error message.

  3. Prior to the Send/Receive process the email does sit in the outbound queue (Outbox).

  4. After a Send/Receive the email is moved to the “sent mail” folder.

  5. Removing the Office installation, deleting all Office registry entries and reinstalling allows it to work temporarily.

  6. Starting Outlook in safe mode seems to always work (at this point) but obviously not the solution i’m looking for.

  7. The only two addons listed in the Outlook settings dialog box are for Symantec Antivirus and Exchange. I’ve disabled both with no effect.

  8. I’ve searched the “addons” key in the registry and it shows no addons installed.

  9. Since “safe mode” seems to work, I suspect there’s a rogue executable at play here. Virus/Adware scans have not turned up any results.

  10. Outlook Express can be configured with the users credentials and performs flawlessly. This rules out any network / server / IP Block issues.

  11. User can send email to self or other users sharing the same domain name

So… I’m baffled! I suspect a full reformat and reinstallation will solve the problem.

EDIT: Note read the problem carefully, the email gets sent fine when in safe mode, or using the same account on another machine.

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Can you elaborate on your environment? Exchange? If so, what version / OS? Who is providing the POP account? Have you contacted them? –  Cypher Sep 29 '10 at 3:22

5 Answers 5

One thing to keep in mind with bizarre problems in Outlook: Quite a bit of information is stored in the MAPI/Mail profile that does not get deleted when it seems it should.

Creating a new profile is relatively painless, and a simple way to test Outlook's config without having to R & R it...

Control Panel, Mail icon.

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I would also suggest it is a relay problem on the SMTP server. My best bet would be that you need to enable "SMTP-Server requires authentication" setting for the SMTP server.

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First thing I usually do is follow the email. Can you telnet to the SMTP server on Port 25 (telnet my.smtpserver.com 25) and get a response? Do you have the ability to look at SMTP logs on the server to see if the email is even getting to it, and if so, is it attempting to deliver? If not, can your ISP see any activity?

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I agree with Brent. It seems to be a classical "relay not allowed" problem on server, or other server issue, and not a client problem.

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Like stated in my edit, the email is sent fine from another machine or in safe mode. –  dswatik May 9 '09 at 16:28

Something in your description doesn't seem to add up. Are you sure it's not a server-side problem?

One way to test would be to set up a gmail account (or other), and use their settings for your outgoing server. If it does, it's likely a problem on the server side (ie. perhaps your computer is in an rbl) Are you using a public IP address, or private on your computer?

It would also be very helpful if you had access to the server-side logs.

Also, are there others on your domain that are having / are not having this same problem?

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