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OBIEE 12C SMTP Configuration error [nQsError:75025] Handshake error

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Shadrack Korir Kirui
Shadrack Korir Kirui Rank 1 - Community Starter
edited Aug 13, 2024 7:21PM in Oracle Analytics Cloud and Server

I am trying to configure my smtp as per the below screenshot

pastedImage_2.png

But I keep getting the error

  AgentID: /users/weblogic/B5EjbFtpTest

[nQSError: 75025] Handshake failed when connecting to SMTP server using SSL.

Can someone please assist me with the correct procedures for configuring microsoft office 365 smtp on obiee 12c to send emails

Thank you,

Shadrack.

«1

Answers

  • [Deleted User]
    [Deleted User] Rank 2 - Community Beginner

    Shadrack,

    The devil is in the detail which in your case means the certificate. What exactly is in the certificate?

    As a hint: recent configs with Exchange (not 365) required specification of depth and cipher list as well.

  • Joel
    Joel Rank 8 - Analytics Strategist

    Just to add to @Christian's point, this isn't an OBIEE issue as such but more of an SMTP server side configuration issue. Can you ping the SMTP server from your OBIEE server? Most times SMTP servers by default deny access so you'll need to ensure that you can access the SMTP server from your OBIEE server (unless this was working before). According to this Oracle Support document, this should work in 12.2.1.3 and above

    EDIT

    According to @SteveF-Oracle in his response in another ODC thread, you need to use an SSL STARTTLS connection security type. In your screenshot, you're using SSL/TLS.

  • Shadrack Korir Kirui
    Shadrack Korir Kirui Rank 1 - Community Starter

    Thank you guys for getting back to me on this quick.

    I think my issue would be the certificate as I have tried using different certificates that I copied from the openssl to the SMTP server and also a self-signed certificate using local CA authority.

    At this point, I'd need help in where to effectively get a SSL certificate to use to configure the SMTP settings. I have been able to connect to the SMTP server from OBIEE server using telnet smtp.office365.com 25/587, my problem here is how do I test if the SSL certificate works with the SMTP server.

    Joel, I had opened an SR with Oracle on the same issue and they advised to upgrade to OBIEE 12.2.1.4, after upgrading it now gives the SSL Handshake error. I have also tested both SSL/TLS and STARTTLS but they both give the same error. Probably a question I'd ask at the moment is, do I have to configure SSL on OBIEE and WLS to be able to send mail using SSL?

    Thanks,

    Shadrack Kirui

  • Gianni Ceresa
    Gianni Ceresa Mod

    Not directly on your topic but related to...

    You don't need your OBIEE to be SSL to connect to a SMPT via SSL. In this SMTP connection your OBIEE acts as the client, therefore the SMTP will never know if your OBIEE is SSL or not etc.

    You said you tested with various certificates and even a self-signed one : that's not how it works. Only the right certificate can work, any other one will end up failing at the handshake as, if I'm not wrong, it's really the initial part of the exchange. As the name says: it's the hand shake like you shake hands when you meet somebody and say "hi".

    If your settings aren't correct it will never go any further as that's what SSL is all about.

    I don't have an Office365 account with a mailserver to even have access to the info on where to get the certificate from etc.

    A random guess: do you really have to provide a certificate? Office365 must use one which is publicly accepted as valid, properly signed by a trusted CA. It's like if your browser would prompt you if you really trust any public website when using HTTPS (like oracle.com, google.com etc.). You are prompted only when the certificate isn't trusted by default, so maybe will the SMTP work in the same way: did you try? If all the settings (port, protocol) are correct, it could maybe work ...

  • Shadrack Korir Kirui
    Shadrack Korir Kirui Rank 1 - Community Starter

    Thank you Gianni, it's all really related to the woes am facing lol, I really appreciate it

    It all makes sense that my issue is not having a correct certificate when using SSL/TLS configuration. I have tried to use port 25 without a certificate and I get [nQSError: 75006] Failed to send MAIL command. 5.7.57 SMTP; Client was not authenticated to send anonymous mail during MAIL FROM . Even when I test using telnet command MAIL FROM: <email> on the OBIEE server I get the same error "5.7.57 SMTP; Client was not authenticated to send anonymous mail during MAIL FROM."

    Would this then mean it's a configuration issue on the SMTP server side? And would that mean that the email will still be sent securely without using a SSL certificate?

    Thank you very much for your assistance.

    Thanks,

    Shadrack Kirui.

  • [Deleted User]
    [Deleted User] Rank 2 - Community Beginner

    Following up on Gianni's input: https://docs.microsoft.com/en-us/office365/enterprise/plan-for-third-party-ssl-certificates

  • Gianni Ceresa
    Gianni Ceresa Mod

    The following is just random guesses ....

    That SMTP message would make me think that the SMTP server simply didn't recognize your client as a valid user allowed to send emails. In the past (15-20+ years ago) many SMTP were just fully open: anyone could send emails around easily. That's how to make life simple for spammers.

    As you can see in https://docs.microsoft.com/en-us/Exchange/mail-flow-best-practices/how-to-set-up-a-multifunction-device-or-application-t…  they says that the client must use TLS/StartTLS and authenticate with username/password of the hosted mailbox.

    I don't know if the steps covered by https://docs.microsoft.com/en-us/exchange/mail-flow/test-smtp-with-telnet?view=exchserver-2019  or https://teamventi.freshdesk.com/support/solutions/articles/4000118549-how-to-check-an-smtp-connection-to-office365-with-…  are still valid. Give it a try, but if you continue to receive the same message maybe also triple check the credentials you are using.

    Can't remember if you can test by telnet a SMTP with authentication...

  • Shadrack Korir Kirui
    Shadrack Korir Kirui Rank 1 - Community Starter

    Great, thank you all very much this all will get me in a much better position to continue troubleshooting this issue

    Much appreciated!

  • Mohammed Tausif Khaleel
    Mohammed Tausif Khaleel Rank 1 - Community Starter

    Hi Shadrack,

    I was wondering if you were able to overcome the issue you were facing regarding SMTP server and your application client.

    Asking this as i'm also in similar situation as you where im not able to establish the connectivity between my client which is OBIEE 11g with SMTP server setup on AWS Simple Email Service (SES), below is the error and configuration that im setting at the OBIEE admin level.

    Can anyone please have a look. Really appreciate if anyone can provide some pointers.

    Im on OBIEE 11.1.0.9 version (going to upgrade soon) and WLS 10.3.6

    Error : Could not establish connection. javax.mail.MessagingException: Could not connect to SMTP host: email-smtp.us-east-1.amazonaws.com, port: 465, response: -1



    Thank you,

    Tausif

  • BrandonH
    BrandonH Rank 5 - Community Champion

    You're probably going to need to pull a more detailed error from the logs. Could not connect isnt much to go on, but behind the scenes its probably another handshake error. See if the logs show anything?