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srinivas2324Flag for India

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Bounce back mails from system administrator in outlook mail client

Hi Guys,

My outlook mail client sometimes bounce back mails giving me the following error:

From: System Administrator
Sent: 25 February 2013 11:00
To: [deleted my email address]
Subject: Undeliverable: RE: RE: RE:
 
Your message did not reach some or all of the intended recipients.
      Subject:    FW: RE: RE: RE:
      Sent: 25/02/2013 11:00
The following recipient(s) cannot be reached:
      [deleted the email address I was sending to] on 25/02/2013 11:00
            550 This message was classified as SPAM and may not be delivered


I managed to found a temporary solution for this by running outlook client in safe mode but I am looking for a permanent solution.

Need help on solving this problem guys ...

Regards,
Srinivas
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DMTechGrooup
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You have Linux listed here.. who is the email server and are there any anit spam systems running on it?
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Hi DMTechGrooup,

We are using cPanel and it has exim mail server. I also stopped spam assassin.

When I am running the outlook client in safe mode the mails are going without any problem.
but when I run normally some times the mails are getting bounced back. I am suspecting if there is a problem with the outlook client.

Regards,
Srinivas
Avatar of Brian B
Does this happen with any address, or is there specific addresses that sometimes fail?

These problems usually have more to do with the recipient's server than your email client. I would also check to make sure that the IP of your outbound mail server has not been blacklisted. If you are paying for an external email service, you may need your ISPs help to narrow that down.

As for your Outlook client, instead of running in safe mode, can you disable scanning of outbound mail within Spam Assassin? That will help narrow down the problem on your own system.
LOL - the mail server rejecting the message is the RECEIVING mail server.
The 550 response is the SMTP error code sent from the RECIPIENT'S mail server back to YOUR mail server, which is being kind enough to relay back to you.

It is possible that your exim server is setup with a bad HELO greeting, but if you're not getting errors from other recipients, that's not likely.

Your next step is to contact the postmaster at the recipient domain to see why they're blocking you.... you could be on an RBL, or have a bad reputation with Symantec or Trend, or whatever SPAM blocking they may have deployed.

Sorry, but unless you have a config error in your server -- which should mean LOTS of blocked messages -- the error will have to be resolved by the recipient.

Welcome to the world of mail hosting and the NEVER ENDING battle against SPAM (which, in recent years is more a battle against SPAM BLOCKERS than against SPAM SENDERS!)

Dan
IT4SOHO
It's not necessarily the receiving email server.  If the sending server checks all outgoing mail then that too can block with the message.  The only true way is to look at the SMTP logs and see.  

In your message in outlook.. are you using images as a signature or anything that when in safe mode it doesn't send or sends in plain text.

Why am I getting this error?
To help in the global battle of ever-increasing spam, we have implemented spam detection procedures on all emails prior to leaving our servers. Each email is evaluated and rated according to spam rules to determine how likely they are to be actual spam. Those that fail the test are returned to the original sender with the error message 550 This message was classified as SPAM and may not be delivered (please see the email below). If you are receiving a bounceback with this error, then the email you sent has not passed the outbound filter.

One example : http://www.inmotionhosting.com/support/edu/everything-email/spam-prevention-techniques/550-spam-message
Hi Guys,

The mail coming from system administrator does not contain any information in the header as it is just blank. so I think this mail is sent internally from the outlook client. I am unable to  find out which is stopping the mails to send.

I am using outlook in safe mode for past 3 days and I never got this bounce back mail from system administrator.

Also when I am using the web mail I don't have any problem.

But only when I am using the outlook client normally I am getting this bounce back mails.

Referring to the below link I got a temporary solution, but I need to find a permanent fix to avoid using outlook client in safe mode always.
http://answers.microsoft.com/en-us/office/forum/office_365hp-outlook/outlook-error-550/52c1c84d-9b99-4d18-bd41-5f56063789c3

Regards,
Srinivas
OK, so the MS article you quote says that this same error message (which is odd, because 550 messages are SMTP server messages -- for other admins in the audience, a 550 message is an MTA receipt error... and Outlook is, in all respects, an MUA, not an MTA!).

Regardless, the MS article says that if you can run Outlook in Safe Mode and it works (as you have described here), then the issue is some kind of an add-in.

Since we haven't heard what version of Outlook you're using, I suggest you google "outlook 2xxx remove add-ins" -- using your version of Outlook: 2000, 2002, 2003, 2007, 2010, or 2013. In any case, remove the add-ins one at a time to find the culprit. Feel free to re-add the good ones... or not.

Dan
IT4SOHO
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srinivas2324, your solution you posted is the almost exact same solution IT4SOHO posted above yours.  It would seem he provided the answer or atleast helped?
This provides a relevant solution