Voice Mail Pro and Microsoft Office 365 - Email sending fails

[kirchenlo]

Hello,

does anyone know if the SMTP email sent via Microsoft Office 365 (outlook.office365.com), which uses TLS on port 995 works?

I have a customer who wants to receive VoiceMailPro recordings and messages via email into it's email client. I tried to setup VMPro with the given credentials and ports but do not get it working. Do you have any idea?

The mail account works properly on thunderbird for example, so it is not related to the credentials.

VMPro runs on a Windows 7 operating system and I have done a wireshark and i can see that there is traffic between outlook.office365.com and VMPro but it looks like the connection is dropped as soon as TLS is started.

Any idea?

[zakabog]

From everything I've seen you're going to need an SMTP relay, VM Pro as far as I know doesn't support TLS authentication, so you'll need to install and configure Outlook on the Windows 7 computer and use MAPI to connect.

[kirchenlo]

Hello All,

here is my solution to the issue with MS Office 365 and VMPro. First of all we all know that neither the IP Office nor the Voice Mail Pro server is actually able to send secure email natively via the MS Office 365 cloud service.

I was struggling around with this a whole day at a customer to find a working solutions. I want to share in my odysee to get it working with you all.

1st Solution / Use the MAPI instead of SMTP on Voicemail Pro Server

That was my first start point and I figured very fast out that MAPI is not at all easy to handle. I tried several MAPI clients (Outlook 2007 / Outlook 2010) none of them were able to sent the emails to the receiver. My issue with MAPI was that VMPro showed me that the message was successfully sent. See below trace out of the debug view.

23/09 16:52:58.732 vmprov5s (66,8) 75c, 730: < CMAPIImpl::SendEmail()
23/09 16:52:58.732 vmprov5s (19,8) 75c, 730: < CMAPIImpl::SendEmail()
23/09 16:52:58.733 vmprov5s (14,9) 75c, 730: Successfully sent email to [email protected]
23/09 16:52:58.733 vmprov5s (14,9) 75c, 730: < EMailerThrd::SendRequestUsingEMAPI()
23/09 16:52:58.733 vmprov5s (14,9) 75c, 730: emailerThrd - SendRequest succeeded for 69\MSG00016

Time was passing quickly as de-installing/installing of VMPro and Office takes a while. The above shows that there was no doubt that VMPro is working but the MAPI client did not do his job by sending the mail on behalf to. The only way it was sending the mail was opening the outlook client and then you could see in the outlook outbox 3-4 messages that have not been yet sent. These messages were sent as soon as outlook was started and synchronizing the mail account. I tried several forums to find a workaround or patch for that behavior, finally I gave up the MAPI client.

I think that these Outlook issues are treated to MS security settings, but unfortunately I couldn’t figure out the blocking point.

2nd Solution / Install a SMTP Relay

I installed the hMail server (5.4 and 5.5) but after the configuration I figured out that it does not support TLS for the connection MS Office 365. So wrong road to success.

3rd and Working Solution / Install STunnel

I use now STunnel which maps the local standard mail ports via a windows service to the secure mail ports used by MS Office 365. STunnel is a multi OS freeware tool. Via the below link you will find information’s about the STunnel and the required setup.

http://en.wikipedia.org/wiki/Stunnel

https://www.stunnel.org/index.html

https://www.stunnel.org/downloads.html

After installing STunnel as a service on the same windows server which is running the VMPro server you will need to setup STunnel configuration file accordingly. In this file you can see that the standard ports for email (25/110) are mapped to the cloud based service.

Example:

# Stunnel configuration file for Office 365 SMTP and POP3
# Author: MessageOps, www.messageops.com
# GLOBAL OPTIONS
client = yes
output = stunnel-log.txt
debug=4
taskbar=yes
# SERVICE-LEVEL OPTIONS
[POP3 Incoming]
accept = 110
connect = outlook.office365.com:995
[SMTP Outgoing]
protocol = smtp
accept = 25
connect = smtp.office365.com:587

On your application you must set the SMTP server to the IP address of the server/PC running STunnel (must not be the same machine as VMPro, it can be any machine within the network) and you need the use in clear the credentials of the MS Office 365 exchange account.
Via the below links you will get a detailed idea how STunnel works.

http://www.messageops.com/office-365-tools-resourc...
http://community.spiceworks.com/how_to/show/50057-...

In the case that you will have such a scenario this will help you that you do not lose too much time, like me. It is a little tricky when your application does not support TLS/SSL. I assume that in future all major suppliers of such applications will adapt their products that maybe in future no more workarounds are needed. For the moment this is for me the only way to get it properly working via MS Office 365.

Regards and have fun.

[hinslr]

365

If you know the admin login to 365 you can use the authentication to avoid whitelisting the public IP the IP office or VMPRO is sending from. If you do not know that you need their IT to whitelist the public address the IP office is sending from and to set up a receive connector. You do not have to set up a relay.