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SMTP Error "Must issue a STARTTLS command first" in ClearPass

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  • 1.  SMTP Error "Must issue a STARTTLS command first" in ClearPass

    Posted Jul 11, 2017 06:00 PM

    Hi experts,

     

    I want to test a SMTP Server configuration for email messaging in CPPM, when I click on Send Test Email I get an error. I can see the details in Monitoring > Event Viewer , which are:

    smtperror1.PNG

     

    I have configured no security connection in the SMTP setting. This is the full configuration:

    smtperror.PNG

    Does this mean CPPM doesn't support SMTP messaging without security or is this imposed by the SMTP server? Is there any workaround or must I use StartTLS security? My CPPM version is 6.6.0.81015.

     

    Regards,

    Julián



  • 2.  RE: SMTP Error "Must issue a STARTTLS command first" in ClearPass

    Posted Jul 11, 2017 06:19 PM

    Hi,

     

    After enabling StartTLS security and importing the SMTP Server certificate to Trust List the error changed to:

    smtperror2.PNG

     

    Did anyone have this kind of errors?

     

    Regards,

    Julián



  • 3.  RE: SMTP Error "Must issue a STARTTLS command first" in ClearPass

    EMPLOYEE
    Posted Jul 11, 2017 06:23 PM

    Are you using port 587? 

    Also, be sure to look in event viewer.



  • 4.  RE: SMTP Error "Must issue a STARTTLS command first" in ClearPass

    Posted Jul 11, 2017 06:29 PM

    Yes, when I selected StartTLS security the port was automatically changed to 587. And the errors I have attached are seen in the Event Viewer.

     

    Regards,

    Julián



  • 5.  RE: SMTP Error "Must issue a STARTTLS command first" in ClearPass

    EMPLOYEE
    Posted Jul 12, 2017 04:36 AM

    Try setting it to SSL for gmail (not StartTLS):

     

    https://community.arubanetworks.com/t5/AAA-NAC-Guest-Access-BYOD/How-to-use-Gmail-as-SMTP-server-on-CPPM/ta-p/185226

     

    Also notice the message if you switch to SSL: SMTP Server certificate must be imported to Trust List as SSL setting is enabled.



  • 6.  RE: SMTP Error "Must issue a STARTTLS command first" in ClearPass

    Posted Jul 12, 2017 11:34 AM

    Hi Herman,

     

    Tried with SSL and now there is a connectivity problem:

    smtperror2.PNG

     

    But I have tried to telnet to that port from my PC and it is open. I don't know where the problem is, but it seems to be impossible :(

     

    Regards,

    Julián



  • 7.  RE: SMTP Error "Must issue a STARTTLS command first" in ClearPass

    EMPLOYEE
    Posted Jul 12, 2017 12:00 PM

    Just tried with gmail and these settings:

    gmail.png

    And that worked fine after I logged in to my Gmail account and enabled 'insecure application access'. I got an email that access was blocked and a similar message in access tracker (Please log in via your web browser and then try again. Learn more at https://support.google.com/mail/answer/78754). BTW I did not need to do anything with the trust list, it just connected.

    If you find the mail server settings for your local Internet Service Provider, that will probably work without authentication (at least it does here).

     

    Does it feel as a 'test email' times out? Could it be that you enabled both data and management interface and the outgoing request is taking the wrong interface (it will take data by default)? I tend to avoid dual interface whenever possible.



  • 8.  RE: SMTP Error "Must issue a STARTTLS command first" in ClearPass

    Posted Jul 12, 2017 12:15 PM

    Hi Herman,

     

    Problem solved! I don't know the reason but testing with the Send Test Email button in the ClearPass Policy Manager > Administration » External Servers » Messaging Setup section didn't work. Then I have tried with Send Test Message button in the ClearPass Guest > Home » Configuration » Receipts » Email Receipt section and worked, I received the test email in my Gmail inbox:

    smtpsuccess.PNG

    BTW, I have tested this successfully with the three security options (none, SSL, StartTLS) and I didn't mind about the trust list as you did.

    I don't know why I get that error with the Send Test Email button in the ClearPass Policy Manager > Administration » External Servers » Messaging Setup section.

    For your last question, I only have configured the management interface.

    Now I will see if it works with a real message...

     

    Regards,

    Julián



  • 9.  RE: SMTP Error "Must issue a STARTTLS command first" in ClearPass

    Posted Nov 01, 2018 08:46 PM

    Been pulling my hair out trying to figure out why the "send test email" keeps failing in the policy manager.  After reading this thread I tested it from guest configuration it works fine. That must be a bug.  Thanks for posting about this my guess TAC would have not known either.



  • 10.  RE: SMTP Error "Must issue a STARTTLS command first" in ClearPass

    Posted May 08, 2019 04:41 AM

    Hi fjulianom,

     

    We have the same issue, and works fine as you said with SSL(port 465):

    1)  I don't import any CA or certificate

    2) Config gmail with allow low security App

    2) Fail send mail through ccpm->external->messaging setup

    3) Probe to send trhough  guest->config -> receipt -> customize email recepit . It works FINE!

     

    Our version of ClearPass is 6.7

     

    Thanks!



  • 11.  RE: SMTP Error "Must issue a STARTTLS command first" in ClearPass

    Posted Jul 12, 2017 12:39 PM

    Hi Herman,

     

    Just to let you know that real messaging worked. BTW, thanks for taking your time and testing this issue.

     

    Regards,

    Julián