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Can't send outgoing messages in Outlook (2007 or 2010) with hyperlinks or headers in message

Posted on 2010-08-16
Medium Priority
Last Modified: 2013-11-30
Platforms: Windows XP, Windows 7
Mail program: Outlook 2007, 2010
ISP hosting: COVAD (DSL)
Anti-Virus: PC Doctor and Zone Alarm

Everyone using addresses with our personalized domain (intensivenutrition.com, e.g. customerservice@intensivenutrition.com, orders@intensivenutrition.com, etc. etc.) cannot send outgoing email with hyperlink or headers in message text.

In order to successfully send an email, forwarded/replies and newly created messages have to have the "header" text removed as well as any active links removed e.g. email addresses, page links, etc. etc. If these items are not removed, an immediate error message is received from the "System Administrator" (which happens to be me, ha!) which reads
Subject: "Undeliverable"
Text: The following recipients cannot be reached. 'olivia.melaugh@gmail.com' on 8/16/2010 12:01 PM
            550 5.7.1 o7GJ0qPV027794 This message does not comply with required standards.

As this is a 5.7.1 message, this is not a permanent error but something to do with filtering or similar problem I think.

These are the steps I have taken thus far which have yielded NOTHING:

1. Deleted and recreated all email accounts (rebooted, etc. etc.)
2. Changed SMTP settings per COVAD instruction. This seems to alleviated some issues with outgoing but still cannot send replies/forwards with header info, etc.
3. Turned off anti-virus
4. Rolled back Windows updates. (One of my guesses is that the problem lies with Microsoft updates and with Outlook.)
5. Reinstalled Windows updates
6. Installed NEW Outlook 2010 onto new machine. Same problem (would eliminate virus as culprit)
7. Spent several hours on phone with COVAD tech support. Confirmed that our domain is not on any blacklists. They also indicated that they don't filter email in the manner in which I described. (it does not appear that the emails are even reaching them so this I believe)

I am able to access my mail using the webmail program offered by COVAD. I am also able to successfully send emails using my husband's MAC and my original email pop3 settings (they don't have to be modified to successfully send email). I installed my email settings on my home computer (which runs Winxp and outlook) and have the same problem so the problem probably isn't viral.

So, my conclusion is that OUTLOOK/Microsoft is the culprit as the outgoing emails don't appear to even reach the server....some kind of filter is bouncing them back.

Another bit of information which may or may not be helpful...
We have received, since this problem began last week, an inordinate amount of spoofing and spam emails.

Help would be very much appreciated. Have no idea how to fix this and Microsoft forums have yielded nothing. My next step is to call them and pay $$$ to have this corrected.

Thanks very much.

Question by:oliviacamille
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LVL 76

Expert Comment

by:David Lee
ID: 33449131
Hi, oliviacamille.

What do you mean by "header text"?  What format are the messages in?

Author Comment

ID: 33451053
Meaning the text that is generated when one replies to or forwards an email identifying the email address and subject, time stamp, etc. etc. of the replied to or forwarded email. This appears at the base of the email.
Additional info: I have recreated new Outlook profiles to no avail (Microsoft's solution...I have to call them back).
Thanks very much.

Author Comment

ID: 33451102
I suppose the issue with the "headers" is that there is an email address and/or active link that triggers some kind of block/filter, etc.
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Expert Comment

ID: 33455114
I noticed similar behaviour today (for the first time) in Outlook 2007 (on an SBS2003 domain). Removing the hyperlink in a Replied to email allowed the mail to go out.

Author Comment

ID: 33455298
Yes, removing the link does work. However, this is not how Outlook should work and I should not have to remove links in order to send outgoing email. Integrating links in email is a necessary function.

Expert Comment

ID: 33455406
Should have made myself clear. I totally agree with you. It is changed behaviour (I guess a security update caused it) and I also need to find a solution. Hopefully someone will jump in, and if I find anything more, I will be sure to post here.

Author Comment

ID: 33456146
Thanks, Frank. Sorry if my email was short. I'm just so frustrated!!!I know you agree with me...it's just ridiculous that these things happen all the time and the only support we get is from techies/experts like you and others on this board. My feeling is that it is some kind of update/security thingy but identifying which one or ones is quite difficult.

Expert Comment

ID: 33457813
I don't claim to be expert in this (but more an admin by default).  However, I do now know that the problem in my case is caused by an incoming email (to which I Replied) in which the URL (when I hover over it) showing: "mhtml: {a registry key.}mid:// etc."followed by the http:// URL. Why that has happened, instead of a regular URL,  I do not (yet) know.

So if your problem is NOT caused by URL of that type, you may have a different issue.
LVL 76

Accepted Solution

David Lee earned 1000 total points
ID: 33459821
From what I see this is a long standing problem and the error message is always generated by the ISP's mail system.  There are numerous reports of this going back a couple of years.  It's also been reported by users of other mail clients.  Mestha, who is an Exchange genius, asserts that the message is not an Exchange message.  Outlook doesn't have the ability to reject messages.  It's a client.  It connects to a mail server and transfers messages.  It's the server that accepts or rejects the message.  It may be a spam control server or an anti-virus server (including anti-virus on the client), but it's almost certainly not the client.

While I don't doubt the evidence you've compiled I don't think it's as conclusive as it might appear.  Web mail does not work the same way that a mail client works, so the fact that the messages work okay when sent through it isn't helpful.  Web mail is a web interface to the mail system.  It doesn't typically connect and send through the same mechanism that a client does.  It's also worth thinking about this in broader terms.  If it was Outlook that's blocking the messages, then no one would be able to send an Outlook message with a hyperlink.  Microsoft would have had to take action by now.

Can you share more details about how the Covad mail service works?  Is it SMTP, IMAP, or Exchange based?  Does it employ a spam and/or anti-virus filter?  


Author Comment

ID: 33538173
Since I posted this question, I have changed hosting/email and domain to Netsol. Same problem. Using SMTP. Have personally checked blacklists. Listed on one and have emailed that list for remedy. I don't think that is the root of the total problem. I switched, btw, because COVAD was unable to provide consistent support. My last foray into Oultook support with Microsoft sent me to India with a tech who was a little bit too friendly and not too helpful. We have moved everything to GMAIL for the present and are able to send/receive successfully with links, hyperlinks, photos, etc.

Assisted Solution

Franklittle earned 1000 total points
ID: 33547114
Hi Olivia. Is the actual error message after the 550 5.7.1. code the same with NetSol as with Covad or has it changed?
What I have now read on the 550/5.7.1 error suggests it is an ISP mailserver issue as BlueDevilFan states. It also goes back certainly to 2006 or earlier and is thus perhaps not related to a recent update after all. Some people reported that it was an ISP spamfilter issue; 'intensive" discussions with the ISP were necessary to track it down.
Do you have SMTP logging enabled in Outlook? (Briefly, to capture the conversation between your Outlook email client and the ISP mailserver): Tools | Options | Other tab | Advanced Options and check Enable logging (troubleshooting) for Outlook 2007. If you send one of the troublesome emails (and then switch logging off again), what does the log say? MS says the default location is: C:\Documents and Settings\user name\Local Settings\Temp\Opmlog.log (see: http://office.microsoft.com/en-us/outlook-help/what-is-the-enable-logging-troubleshooting-option-HA001230421.aspx?CTT=1)

Author Comment

ID: 34800334
This question can be closed. The solution proved to be the fault of the ISP although COVAD would not admit any responsibility on their end for the email block. Thank you for all your help.

Author Closing Comment

ID: 34800351
The problem was with the ISP. COVAD denied any responsibility and as a consequence we switched ISPs. Once that happened, email returned to normal. Apparently there was some blocking going on of our domain by the ISP. This is something to keep in mind.

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