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Exchange server 2007 in relayy mode and EHLO response RRS feed

  • Question

  • Issue Using javamail based client to send emails using SMTP wth Exchange server 2007 setup with Frontend receive connector using "Externally Secured" auth option

    Observation: When telnetting to such an exchange server or using javamail to connect to it, the server responds with the following verbs to the EHLO message sent byy the client.

    250-AUTH

    250-PIPELINING

    250-XECHG50

    250-X-ANONYMOUSTLS

    250-X-EXPS NTLM

    ....among other verbs

    Note that , however, since the 250-AUTH verb doesn't have any arguments the javamail client isn't able to proceed with authentication as it fails to narrow down on a suitable mechanism.

    This should not happen. In exchange server 2016 the server setup with same option of "Externally Secured" doesn't have AUTH verb in the EHLO response at all and so the client rightly is able to proceed.

    Is this a known issue with exchange server earlier versions 2007? is there a patch available , this looks like a bug.

    thanks

    Saturday, November 12, 2016 5:31 PM

All replies

  • Issue Using javamail based client to send emails using SMTP wth Exchange server 2007 setup with Frontend receive connector using "Externally Secured" auth option

    Observation: When telnetting to such an exchange server or using javamail to connect to it, the server responds with the following verbs to the EHLO message sent byy the client.

    250-AUTH

    250-PIPELINING

    250-XECHG50

    250-X-ANONYMOUSTLS

    250-X-EXPS NTLM

    ....among other verbs

    Note that , however, since the 250-AUTH verb doesn't have any arguments the javamail client isn't able to proceed with authentication as it fails to narrow down on a suitable mechanism.

    This should not happen. In exchange server 2016 the server setup with same option of "Externally Secured" doesn't have AUTH verb in the EHLO response at all and so the client rightly is able to proceed.

    Is this a known issue with exchange server earlier versions 2007? is there a patch available , this looks like a bug.

    thanks

    Exchange 2007 is out of extended support in less than 6 months. If you are running it with the last SP and RU that was released, then that's as far as it will go. If there is a bug , it won't be addressed. My point it, there is no reason you should be trying to make this work with a dead version.


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    Saturday, November 12, 2016 6:21 PM
  • can you please confirm if this behavior(EHLO response having no argument 250-AUTH ) is erroneous and that it is fixed in subsequent versions and which specific version? my testing indicates 2016 exchange doesn't exhibit this behavior. My customer is using the older versions of exchange so am looking for a solution to help him. I can then tell him to move to a version that works.

    thx

    Sunday, November 13, 2016 6:50 AM
  • If your testing shows 2016 works as expected, then you have your answer. Perhaps use the client receive connector and submit on port 587 instead.

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    Sunday, November 13, 2016 2:31 PM