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New Contributor II

SMTP with Office365

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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?

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Anonymous
Not applicable

Re: SMTP with Office365

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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.

View solution in original post

11 Replies
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Honored Contributor
Honored Contributor

Re: SMTP with Office365

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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. 



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New Contributor II

Re: SMTP with Office365

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

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Valued Contributor II
Valued Contributor II

Re: SMTP with Office365

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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

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Valued Contributor II
Valued Contributor II

Re: SMTP with Office365

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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

....

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New Contributor II

Re: SMTP with Office365

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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.

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New Contributor

Re: SMTP with Office365

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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

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New Contributor II

Re: SMTP with Office365

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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.

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Anonymous
Not applicable

Re: SMTP with Office365

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

Thanks,

Matt

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New Contributor

Re: SMTP with Office365

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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.

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