11 Replies Latest reply on Jan 6, 2014 11:16 PM by ronaldbyrd

    SMTP with Office365

    ronaldbyrd New Member

      Version:

      ADTRAN, Inc. OS version R10.8.0.E

      Boot ROM version A2.06.B2.01

      Platform: NetVanta 7100, part number 1200796E1


      Config:

      domain-proxy

      name-server 8.8.8.8 8.8.4.4

       

      event-history on

      no logging forwarding

      logging email on

      logging email receiver-ip smtp.office365.com port 587 auth-username XXXX@YYYY.us auth-password ZZZZ

      logging email address-list XXXX@YYYY.us

      logging email error-report address-list XXXX@YYYY.us

      logging email sender XXXX

       

      voice user 234

        connect sip

        cos "normal_users"

        first-name "XXXX"

        last-name "XXXX"

        password "XXXX"

        group-ring-call-waiting

        findme-followme enhanced

        coverage global go_to_voicemail

        sip-authentication password "XXXX"

        alias XXXX

        email XXXX@YYYY.us

        email-secondary XXXX@YYYY.us

        voicemail auth-mode password

        voicemail greeting default

        voicemail cos normal_voicemail

        voicemail notify email attach-message pcm

        voicemail password "XXXX"

        script "script-1"

          action 1 internal 234 no-press-to-accept ring-time 24

          action 2 vm 234

        script "script-2"

        script "script-3"

          action 1 internal 234 no-press-to-accept ring-time 24

          action 2 vm 234

        contact-group 1

          name "Priority"

          description "Priority contacts"

          presence available script "script-1"

        contact-group 2

          name "Blacklist"

          description "Undesired contacts"

          ringback

          presence available script "script-2"

        contact-group 3

          name "Everyone"

          description "All other contacts"

          implicitly-include all

          ringback

          presence available script "script-3"

          permit-caller-id number UNKNOWN

        voicemail notify schedule Sunday 12:00 am

          notify email primary

       

      Debug:

      SMTP Response: 220 CO1PR07CA010.outlook.office365.com Microsoft ESMTP MAIL Service ready at Mon, 30 Sep 2013 14:17:04 +0000

      To SMTP server: EHLO [X.X.X.X]

       

       

      To SMTP server: 22 bytes of data

      SMTP Response: 250-CO1PR07CA010.outlook.office365.com Hello [X.X.X.X]

      SMTP Response: 250-SIZE 78643200

      SMTP Response: 250-PIPELINING

      SMTP Response: 250-DSN

      SMTP Response: 250-ENHANCEDSTATUSCODES

      SMTP Response: 250-STARTTLS

      SMTP Response: 250-AUTH

      SMTP Response: 250-8BITMIME

      SMTP Response: 250-BINARYMIME

      SMTP Response: 250 CHUNKING

      To SMTP server: STARTTLS

       

       

      To SMTP server: 10 bytes of data

      SMTP Response: 220 2.0.0 SMTP server ready

      To SMTP server: AUTH PLAIN

       

       

      To SMTP server: 12 bytes of data

      Invalid server message: 503 5.5.2 Send hello first

       

      Problem:

      Office 365 requires TLS. I have verified the username and password. Any ideas?

        • Re: SMTP with Office365
          jayh Hall_of_Fame

          If Office 365 is capable of delivering email from the Internet, they would need to have a server listening on port 25 that doesn't require TLS or authentication as long as you are sending to a domain hosted on Office 365. 

           

          You will need authentication to:

          • Retrieve email sent to a specific mailbox
          • Use the Office 365 service to relay mail outside of your domain

           

          Regardless if YYYY.us is a domain hosted on Office 365,  sending unencrypted email without authentication to port 25 of MX record for YYYY.us should get it delivered regardless of the internal handling for TLS, etc. 



            • Re: SMTP with Office365
              ronaldbyrd New Member

              From what I keep reading on these forums and according to the release notes, as of AOS R10.8.0 TLS is supported.

                • Re: SMTP with Office365
                  markfreeman Employee

                  Ronald,

                  You are correct, per the R10.8.0 Release notes:

                  Support cloud based email services such as Gmail, Yahoo, or Hotmail.

                  The Voicemails to Emails email delivery method has been added to safely and securely delivery of

                  voicemails to an online cloud-based email provider. The NetVanta 7000 Series

                  supported SMTP-based email delivery in the past, but this new enhancement builds on SMTP and supports

                  TLS-based security.

                  Benefits

                  - Provides the best of both premises-based voice and cloud-based UC features

                  - No need for dedicated email servers

                  - Encrypted, secure, and robust delivery, reducing response time to voicemails

                  Configuration

                  - No additional configuration is required. The system will begin using SMTP and if a TLS request comes

                  from the server, it will automatically transition to TLS.

                   

                   

                  From my testing with gmail. the auth-username only worked for me when I left off the domain for example mfreeman@gmail.com did not work, but just leaving mfreeman did work

                   

                  Also can you provide a debug output with "debug system" that is what will show the output when trying to send emails.

                   

                  -Mark

                  1 of 1 people found this helpful
                  • Re: SMTP with Office365
                    markfreeman Employee

                    Well looking at your debug, looks like you ran that command, here is what my output had. The big difference I had is that mine said "SMTP Response: 220 2.0.0 Ready to start TLS" where your said "SMTP Response: 220 2.0.0 SMTP server ready"

                     

                    SMTP Response: 220 mx.google.com ESMTP ex7sm2047760vdb.4 - gsmtp

                    To SMTP server: EHLO [X.X.X.X]

                     

                    To SMTP server: 22 bytes of data

                    SMTP Response: 250-mx.google.com at your service, [x.x.x.x]

                    SMTP Response: 250-SIZE 35882577

                    SMTP Response: 250-8BITMIME

                    SMTP Response: 250-STARTTLS

                    SMTP Response: 250-ENHANCEDSTATUSCODES

                    SMTP Response: 250 CHUNKING

                    To SMTP server: STARTTLS

                     

                    To SMTP server: 10 bytes of data

                    SMTP Response: 220 2.0.0 Ready to start TLS

                    To SMTP server: AUTH PLAIN

                     

                    To SMTP server: 12 bytes of data

                    To SMTP server: AGFkdHJhbnRyYWluaW5nNzcAYWVrZGIxOTc3

                     

                    To SMTP server: 38 bytes of data

                    SMTP Response: 235 2.7.0 Accepted

                    To SMTP server: MAIL FROM: <EventMgr>

                     

                    To SMTP server: 23 bytes of data

                    SMTP Response: 250 2.1.0 OK ex7sm2047760vdb.4 - gsmtp

                     

                    To SMTP server: RCPT TO: <mark@yahoo.com>

                     

                    To SMTP server: 35 bytes of data

                    SMTP Response: 250 2.1.5 OK ex7sm2047760vdb.4 - gsmtp

                     

                    To SMTP server: DATA

                     

                    To SMTP server: 6 bytes of data

                    SMTP Response: 354  Go ahead ex7sm2047760vdb.4 - gsmtp

                    ....

                    1 of 1 people found this helpful
                      • Re: SMTP with Office365
                        ronaldbyrd New Member

                        Ok I did a little more research and found this.

                         

                        http://www.ietf.org/rfc/rfc3207.txt

                         

                        Apparently an EHLO is supposed to be sent again after the STARTTLS. Looking at the debug data it clearly isn't. The reason it works with Gmail is because Gmail doesn't enforce this second EHLO but Microsoft does. Adtran may want to add this to their next release.

                        1 of 1 people found this helpful
                          • Re: SMTP with Office365
                            bamajam New Member

                            Looks like we are suffering from this too.  We have a NetVanta 7060 with firmware version R10.8.0.E connecting to an internal 2007 Exchange Server.

                             

                            SMTP Response: 220 mail.abc.com Microsoft ESMTP MAIL Service ready at Wed, 2 Oct 2013 09:30:19 -0500

                            To SMTP server: EHLO [192.168.1.11]

                            To SMTP server: 21 bytes of data

                            SMTP Response: 250-mail.abc.com Hello [192.168.1.11]

                            SMTP Response: 250-SIZE

                            SMTP Response: 250-PIPELINING

                            SMTP Response: 250-DSN

                            SMTP Response: 250-ENHANCEDSTATUSCODES

                            SMTP Response: 250-STARTTLS

                            SMTP Response: 250-X-ANONYMOUSTLS

                            SMTP Response: 250-AUTH NTLM

                            SMTP Response: 250-X-EXPS GSSAPI NTLM

                            SMTP Response: 250-8BITMIME

                            SMTP Response: 250-BINARYMIME

                            SMTP Response: 250-CHUNKING

                            SMTP Response: 250-XEXCH50

                            SMTP Response: 250 XRDST

                            To SMTP server: STARTTLS

                            To SMTP server: 10 bytes of data

                            SMTP Response: 220 2.0.0 SMTP server ready

                            To SMTP server: AUTH PLAIN

                            To SMTP server: 12 bytes of data

                            Invalid server message: 503 5.5.2 Send hello first

                            1. VoiceMail.MailboxManager: 2013.10.02 09:30:34 G729ToPCMConvert converted username_10022013_0930.wav but send failed

                             

                            Any ideas for a workaround or fix?

                            Thanks

                              • Re: SMTP with Office365
                                ronaldbyrd New Member

                                I have an SMTP relay on my network for older printers that don't support TLS. For the time being I am using that. Basically it's a Windows 2008 r2 server that is accepting regular SMTP on port 25 and then it is making the TLS connection to my Office365 server in the cloud and sending the mail. Since you have the Exchange server on site you should be able to create a new receive connector with TLS disabled and limit it to the 7060's IP address.

                      • Re: SMTP with Office365
                        Employee

                        Here is a related thread that provides some potential workarounds: Re: VM to Email failure

                         

                        Thanks,

                        Matt

                        1 of 1 people found this helpful
                          • Re: SMTP with Office365
                            bamajam New Member

                            Thanks Matt.  As Mr Byrd suggested, I created a new receive connector on my Exchange server to catch these emails.  Configured it to accept anonymous connections but only from the IP of the NetVanta and also put it on a specific port number.  That got it working.

                          • Re: SMTP with Office365
                            Employee

                            I just wanted to update this post to mention that AOS R10.9.2 was recently released, which included a fix for e-mail servers that use TLS.

                              • Re: SMTP with Office365
                                ronaldbyrd New Member

                                Thank you Matt. I have upgraded my 7100 and tested the SMTP with Office365 and it does work now that a second EHLO is being sent. I have changed the correct answer on the thread to Matt's post. (Debug output below)

                                 

                                To SMTP server: EHLO [x.x.x.x]

                                To SMTP server: 22 bytes of data

                                SMTP Response: 250-xxx.outlook.office365.com Hello [x.x.x.x]

                                SMTP Response: 250-SIZE 78643200

                                SMTP Response: 250-PIPELINING

                                SMTP Response: 250-DSN

                                SMTP Response: 250-ENHANCEDSTATUSCODES

                                SMTP Response: 250-STARTTLS

                                SMTP Response: 250-AUTH

                                SMTP Response: 250-8BITMIME

                                SMTP Response: 250-BINARYMIME

                                SMTP Response: 250 CHUNKING

                                To SMTP server: STARTTLS

                                To SMTP server: 10 bytes of data

                                SMTP Response: 220 2.0.0 SMTP server ready

                                To SMTP server: EHLO [x.x.x.x]

                                To SMTP server: 22 bytes of data

                                SMTP Response: 250-xxx.outlook.office365.com Hello [x.x.x.x]

                                SMTP Response: 250-SIZE 78643200

                                SMTP Response: 250-PIPELINING

                                SMTP Response: 250-DSN

                                SMTP Response: 250-ENHANCEDSTATUSCODES

                                SMTP Response: 250-AUTH LOGIN

                                SMTP Response: 250-8BITMIME

                                SMTP Response: 250-BINARYMIME

                                SMTP Response: 250 CHUNKING

                                To SMTP server: AUTH LOGIN

                                To SMTP server: 12 bytes of data

                                SMTP Response: 334 VXNlcxxxxxxx

                                To SMTP server: YWRtaWxxxxxxxxxxxxxxxxxxxxxxxxxxxxxx=

                                To SMTP server: 38 bytes of data

                                SMTP Response: 334 UGFxxxxxxxxx

                                To SMTP server: OTlTaGxxxxxxxxxx

                                To SMTP server: 18 bytes of data

                                SMTP Response: 235 2.7.0 Authentication successful

                                BLAH BLAH BLAH more email stuffs......