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How can I get Outlook 2010 to notify me when the server returns 550 (Recipient unknown)?

Unanswered How can I get Outlook 2010 to notify me when the server returns 550 (Recipient unknown)?

  • Wednesday, May 02, 2012 5:22 PM
     
     
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    Here is an example of what is happening from the server logs:

    Wed 2012-05-02 12:46:07: [3563:1] <-- RCPT TO: <invalidaddress@domain.local>
    Wed 2012-05-02 12:46:07: [3563:1] Sender attempted to deliver message to unknown address
    Wed 2012-05-02 12:46:07: [3563:1] --> 550 <invalidaddress@domain.local>, Recipient unknown
    Wed 2012-05-02 12:46:10: [3563:1] <-- QUIT
    Wed 2012-05-02 12:46:10: [3563:1] --> 221

    In Outlook 2003 on Windows XP, an message shows up in the inbox with a special icon and says it is from System Administrator.  This message indicates the e-mail could not be delivered.

    In Outlook 2010 on Windows 7, nothing shows up in the inbox, and the user thinks the mail was sent successfully.  The server didn't accept it, so it doesn't send a bounce.  I have recently seen a similar message in Outlook 2010 similar to what shows up in Outlook 2003, but it was for an outside domain and not caused by a 550.  As such, I tested on my instance of Outlook 2010 and confirmed that this doesn't happen (I then collected the log excerpt above).  I am not certain what the message I did see was caused by, but I believe it was an e-mail address that Outlook couldn't parse, meaning the server wasn't involved.

    We are not currently using Exchange, and there is no policy configured regarding Outlook.  I do need to make Outlook 2010 notify users when the server refuses mail across our site and on future computers, so policy would probably be the best way to go about it, but I'm not sure if and/or how I can change this behavior.  Please let me know if you have any ideas.

     

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  • Friday, May 04, 2012 3:30 AM
     
     
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    Hi,

    Track all messages that you send, follow these steps:

    1. Click the File tab.
    2. Click Options.
    3. Click Mail.
    4. Under Tracking, select the Delivery receipt confirming the message was delivered to the recipient's e-mail server or Read receipt confirming the recipient viewed the message check box.

     TIP    As a best practice, consider tracking only single messages of importance instead of all messages. Recipients who occasionally receive a notification that a read receipt is requested on your message are more likely to send a read receipt than if they are prompted every time that they receive a message from you.

    More information, see: http://office.microsoft.com/en-us/outlook-help/get-delivery-and-read-receipt-confirmations-HP010355029.aspx

    Best regards.

    William Zhou

    TechNet Community Support

     
  • Friday, May 04, 2012 5:03 AM
     
     
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    Hello,

    Follow the link below to get the delivery receipt for mails. It may help you.

    http://office.microsoft.com/en-us/outlook-help/add-tracking-to-email-messages-HA010355569.aspx

     
  • Friday, May 04, 2012 12:50 PM
     
     
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    I don't want to track all messages.  Actually, I don't want to track ANY messages.  I simply want Outlook to tell me when it gets an error from the server instead of 100% acting like it sent an e-mail that it didn't send.  As can be seen it the log excerpt I posted, no e-mail was sent over that SMTP session, a 550 was received in response to the RCPT and then Outlook disconnected with a QUIT (at no point was this message on the server, so it's not like the server can send a bounce e-mail back).  It's bad enough that Outlook 2010 moves the e-mail from Outbox to Sent Items even though it wasn't sent, but even worse that it gives no indication that it did this.  Outlook 2003 moved the message that wasn't sent from Outbox to Sent Items as well (which was bad then too), but at least it placed an error in the inbox to indicate that delivery failed.

    Don't get me wrong, I appreciate the suggestion, but for the record, I am aware of receipt functionality, and it is of no benefit for (at least) the following reasons:

    1. It only confirms delivery, even if it notificed users a message wasn't delivered after a set amount of time, that woud be way too late
    2. Many users disable receipt responses in their clients because they believe the functionality is only used by spammers to confirm valid addresses
    3. Most of my users are not technically savvy, and when they get the prompt for sending a receipt they will get scared and hit the X on the prompt window instead of reading and responding to the prompt.
     
  • Friday, May 04, 2012 12:51 PM
     
     
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    Thanks for the suggestion, but see my response to the previous poster above.
     
  • Thursday, January 10, 2013 7:09 PM
     
     
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    Hi PRDIT...I realize this post is from may 2012 but I am having the same issue right now with Outlook 2010.  Did you ever get this resovled?  Thank You!
     
  • Thursday, January 10, 2013 8:02 PM
     
     
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    Sorry, I never found a solution.  I am now running Exchange, so I don't know if this still affects us, but if it does, I'm sure it'll be a problem eventually (I don't think Exchange even keeps logs like the one in my OP by default).
     
  • Friday, January 11, 2013 3:02 PM
     
     
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    Ah, well thank you for the response.   I may end up re-installing Outlook to see if the install somehow got hosed up along the line.  
     
  • Friday, January 11, 2013 3:10 PM
     
     
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    Ah, well thank you for the response.   I may end up re-installing Outlook to see if the install somehow got hosed up along the line.  

    May be worth a shot, but FYI, I had this issue on multiple machines, I think it is an MS change that may or may not have a fix/workaround available.