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Command not recognized, syntax error RRS feed

  • Question

  • We have a 2008R2 server running 2010 Exchange.  We also have a Watchguard Firebox X firewall.  When a user tries to send an email to a specific domain this is what we get:

    Requested rejected your message to the following e-mail addresses:
     
    SOMEONE@ANYWHERE.com (SOMEONE@ANYWHERE.com)
     
    Requested gave this error:
    Syntax error, command unrecognized
     
    A problem occurred during the delivery of this message to this e-mail address. Try sending this message again. If the problem continues, please contact your helpdesk.
     
     
     
     
     
     
     
    Diagnostic information for administrators:
     
    Generating server: SERVER.local
     
    SOMEONE@ANYWHERE.com
    Requested #500 Syntax error, command unrecognized ##
     
    Original message headers:
     
    Received: from SERVER08.local ([fe80::19bb:83ca:bcd9:5df0]) by
    SERVER.local ([fe80::19bb:83ca:bcd9:5df0%10]) with mapi id
     14.02.0309.002; Wed, 16 Jan 2013 14:28:41 -0600
    From: JANE DOE <JDOE@ABCD.org>
    To: "SOMEONE@ANYWHERE" <SOMEONE@ANYWHERE>
    Subject: Test
    Thread-Topic: Test
    Thread-Index: Ac30KBGEKUIS4491S0auFvhXwESzGA==
    Date: Wed, 16 Jan 2013 20:28:40 +0000
    Message-ID: <133E851535BEC94081F6DD3989CAC86F1270665D@SERVER.local>
    Accept-Language: en-US
    Content-Language: en-US
    X-MS-Has-Attach:
    X-MS-TNEF-Correlator:
    x-originating-ip: [192.168.0.121]
    Content-Type: multipart/alternative;
            boundary="_000_133E851535BEC94081F6DD3989CAC86F1270665DSERVERGB_"
    MIME-Version: 1.0
     
    I also attempted to telnet to this email account:

    220 SERVER.local Microsoft ESMTP MAIL Service ready at Wed, 16 J
     2013 20:06:49 -0600
    HELO server.local
    250 Server.local Hello [173.xx.x.xxx]
    MAIL SOMEONE@ANYWHERE.COM
    250 2.1.0 Sender OK
    RCPT jdoe@abcd.org
    250 2.1.5 Recipient OK
    DATA
    354 Start mail input; end with <CRLF>.<CRLF>
    this is a test.

    test.

    .
    250 2.6.0 <7dfb897c-ef1f-428b-8f56-6ff5d935468b@SERVER.local> [I
    ernalId=12509] Queued mail for delivery
    451 4.7.0 Timeout waiting for client input


    Connection to host lost.

    Press any key to continue...

    Thursday, January 17, 2013 2:33 AM

Answers

  • Your telnet worked.  The timeout and connection lost messages are expected since you didn't type quit.  Anyway, are you saying inbound mail doesn't work or outbound mail isn't working?  I'd look at protocol logging on the send or receive connectors within exchange, and then within the appliance if necessary.


    Mike Crowley | MVP
    My Blog -- Planet Technologies

    Friday, January 18, 2013 9:38 PM
    Moderator

All replies

  • Your telnet worked.  The timeout and connection lost messages are expected since you didn't type quit.  Anyway, are you saying inbound mail doesn't work or outbound mail isn't working?  I'd look at protocol logging on the send or receive connectors within exchange, and then within the appliance if necessary.


    Mike Crowley | MVP
    My Blog -- Planet Technologies

    Friday, January 18, 2013 9:38 PM
    Moderator
  • Hi,

    Please have a test to check if other users can send mail to the mail address.

    Please check the tracing logs in the edge server to find why the edge server can not deliver the mail to the destination.


    Please remember to click “Mark as Answer” on the post that helps you, and to click “Unmark as Answer” if a marked post does not actually answer your question. This can be beneficial to other community members reading the thread.

    Sean Xiao
    TechNet Community Support

    Tuesday, January 22, 2013 3:26 AM
    Moderator