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  • issues with sending 50+ emails in BCC

    Hello,

    If anyone knows a better place for me to post this since it's so exchange specific, please let me know.

    I have a department head that has been getting this to work for years, but now has an issue. He sends an email to about 50-100 of his staff in the BCC via a distribution list or by selecting all the unique emails.

    Nobody is getting the mails external to our organization when he tries this but if we test it with a just a few emails...no problem. This issue occurs with web or outlook client. If a local address is in the list those people get it...so I'm rather confused.

    The returned message that comes later in the day is:

    Delivery has failed to these recipients or distribution lists:

    [email protected] Microsoft Exchange has been trying to deliver this message without success and has stopped trying. Please try sending this message again, or provide the following diagnostic text to your system administrator.

    Suggestions or ideas?
    Is there a default setting in Exchange for how many emails can be sent in one transaction?

  • #2
    Re: issues with sending 50+ emails in BCC

    It's most likely not your Exchange, but the mail handlers at the destination. Sending large #s of emails to several recipients in the same mail domain that is outside your own is looked upon as a 'mass mailing worm' or other spam. Some mail systems will pass the email to the recipient and tag it as possible spam. Others will simply drop it. Either way, you get nothing back.

    Assume an email to 25 external users. Some get the message, some don't. You can verify whether your Exchange sent them all by using the Message Tracker tool installed on your Exchange server. As long as you know who sent the message and when, you should get a list back which shows you all the steps taken to process the message to each recipient, all the way to the hand-off between your outside-facing mail server and your ISP's mail relay. If your count matches what you think went out, they were discarded somewhere outside of your control.

    If all of the 'dropped' messages were to the same mail domain (like all to yahoo.com, for example), you can try contacting them to find out why. Or one of the missed recipients could, since they're the ones not getting the bona-fide messages.

    Good hunting!
    *RicklesP*
    MSCA (2003/XP), Security+, CCNA

    ** Remember: credit where credit is due, and reputation points as appropriate **

    Comment


    • #3
      Re: issues with sending 50+ emails in BCC

      Thanks for your time...a couple of comments/questions...

      1. We have done this for years w/o issue. It's not like we are bombing hundreds+
      2. The list is everything including major public domains (yahoo, gmail, hotmail) as well as dozens of private (unique) domains. Unless they all changed their policy in the last few months, something has changed.

      I am slightly familiar with the message tracker and dialed up an mail sent and under ReceipientStatus (for the example I'm looking at) the message is "250 2.1.5 Accepted for you"but I'm clearly looking at a return email for the sender that states "Delivery is delayed to these recipients or distribution lists: [email protected]"

      Could the fact one email on the list is getting rejected make all emails on the listed show up in the rejection email? From what I understand the sender says they got no confirmation from anyone that they got the email...yet I"m looking at dozens of "250" messages in the ReceiptStatus.

      I am googling right now and I do see posts about people stating they get a 250 but nobody is home.

      NOTE: I tried this through our ISP smart host as well as our own smtp with the same results.

      Comment


      • #4
        Re: issues with sending 50+ emails in BCC

        Yes, a single refusal will give you an error message that looks like all of them were kicked back, but each error message should highlight one failed address out of the original header of multiples.

        Your original problem said '...but if we test with just a few...' everything works fine. So no error messages? But that would point at either how many messages or how much data is being sent (50 recipients, each getting a message of 2MB comes to 100MBytes total sent data).

        Have you tried sending the same message, multiple times, but with progressively more recipients each time to see when the errors show up? If you use Message Tracker to search for all messages sent by the one sender, within a 5-minute window of when he clicked 'send' for one of these emails, you should see results for that many of the same message leaving your system. If every one was handed off to your ISP's relay, that's where to go next. That's where I'd concentrate my search first.
        *RicklesP*
        MSCA (2003/XP), Security+, CCNA

        ** Remember: credit where credit is due, and reputation points as appropriate **

        Comment


        • #5
          Re: issues with sending 50+ emails in BCC

          Thanks again. I've included a screenshot of the returned error message...it seems to reference they are all offending...rather odd.

          No attachments so I would not be exceeding any file size limit unless the default is abnormally low and I've increased the exchange attachment size limits to varying success for other needs.

          It actually appears to be working now after a week of issues so I have no clue what the issues were at work. As mentioned I tried our ISP smart host as well as our local domain with the same results.

          Only AOL are getting returned now stating we are rejected due to spam although any check with RBL shows we are 100% clean...AOL has their own issues that may have been triggered by my continued tests to their domain.
          Attached Files

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          • #6
            Re: issues with sending 50+ emails in BCC

            Usually, a returned message includes the error codes. As you probably know 250 is a success message and is a status code as opposed to an error code. The 2.1.5 means the address is OK.

            How is your outgoing mail handled? Do you use a filtering service such as MessageLabs? If so, speak to them as they will be able to tell you what's happening. If you don't, speak to whoever handles the SMTP traffic for your domain.
            A recent poll suggests that 6 out of 7 dwarfs are not happy

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