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TheOpposite

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Outlook 2010 Will Not Send Email Messages

I am working on a strange email issue.  I have a client who is running Windows 7 Pro and Microsoft Office Home and Business 2010.  She has one single POP3/SMTP Internet email account set up in Outlook.  She has been running like this for years with no issues.  Yesterday we realized none of her outgoing messages were being delivered.  I've been playing around with it all morning and can't figure out what is going on.  What I've done and where we are at is outline below:

1)  Outlook Account Settings Test passes with no issue.
2)  Outlook appears to send outgoing messages (they leave the Outbox immediately with no errors).
3)  Messages correctly appear in the "Sent Items" folder.
4)  The message is never received on the other end.  I've tried sending to at least 10 different addressees on different domains.
5)  User can send email to her own address.  Only address that works.
6)  Web host is Newtek Technology Services,  Webmail sending works normally.
6)  Set up the account in Mozilla Thunderbird on same machine.  Works normally.
7)  Set up the account in Outlook on a different machine.  Works normally.
8)  Set up the account in a new Outlook profile on same machine.  Does not work.
9)  Set up the account in a new Windows profile in Outlook on same machine.  Does not work.
10)  Completely removed Office 2010 and AVG Internet Security 2012, rebooted and reinstalled just Office.  Set up account in new profile.  Still doesn't work.

I'm stumped as to what it could be.  Very strange that Outlook appears to send normally but the message just disappears (other than moving to sent).  Also strange that the mail server seems to be functioning normally as the account works from Thunderbird, webmail and Outlook on a different machine.  Not sure where else to go.  Any suggestions would be appreciated.
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Michael Ortega
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When you mention "works on other machines", do these other machines reside on the same network as the computer in question?

MO
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TheOpposite

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No.  They are on different completely different networks.  Different ISP as well.
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Michael Ortega
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Thought about that and I will give them a call, but Thunderbird works fine from her machine so that leads me to think it is an Outlook problem.
Ahh, I thought that you were using Thunderbird from a machine other than her machine on a different network. That does make this a bit more mysterious. It sounds to me like Outlook on that computer could be the culprit.

You have remvoed all AV from the system right? I saw you removed AVG IS 2012 and just wanted to make sure that it's still removed from the system.

How about getting a packet capture going from that laptop using Wireshark just to verify at least that when using Outlook the emails are actually leaving making it to the network and transmitting? Won't necessarily tell us what the problem is, but it would at least confirm whether or not the issue is truly isolated to Outlook.

MO
So I ran the packet capture using Wireshark and it look like the packets are hitting the network.  I'm not super familiar with packet sniffing but I certainly see the email there on the correct port and then the quit command right after.  Also ran it with Thunderbird sending and it looked similar.  So it seems Outlook is in fact sending it out and it is getting dropped by the ISP or email host?
Just got off the phone with the email host.  Turns out the public IP of my customer has been listed as high risk by CommTouch and that is why the messages have been filtered along the way.  He was unable to explain to me why the messages were able to be sent from Thunderbird while not from Outlook.  So that is still a mystery to me.  Anyway I have filed a request with CommTouch to allow sending from this address, we'll see what happens.
Yeah, I thought that was the original problem, but Thunderbird was causing some conflict in that theory.

MO