Voice Mail Pro and Microsoft Office 365 - Email sending fails 3

[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?

 

[hairlessupportmonkey]

Just use a different smtp relay. Perhaps use the one their ISP supplies, or a third party supplier of smtp relay for the voicemail server.

ACSS - SME
General Geek

 

[teletechman]

I have this set up and it is.
smtp.office365.com
port 587 for TLS
click TLS and Authentication username and password
Works good
Mike

 

[az2mia]

Voicemail pro will not encrypt the voicemail-to-email messages. I'm curious how you're able to make that office365 work...

I've always had to set up hMailServer, which encrypts the message and forwards it via gmail.

Here's a setup guide:

https://ceics.com/support/google-mail-smtp-relay-solution

It's been very reliable across numerous installs and years of continuous use with no hiccups.

 

[teletechman]

Sorry was thinking embedded Rls. 9.0.3, I use hMail also.
Mike

 

[kirchenlo]

Hello All,

here is my solution to the issue. First of all we all now that neither the IP Office nor the Voice Mail Pro server is able to sent secure email natively via the MS Office 365 service. I was struggling now around with this issue yesterday at a customer and tried to find a solutions. I want to share in my odysee to get taht 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) non of them were able to snet 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 myemail@mydomain.com
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 I saw in the outbox 3-4 messages that have not been sent. These messages were sent as soon as I opened outlook. I tried several forums to find a workaround patch for that behavior, finally I gave up the MAPI client.

2nd Solution / Install a SMTP Relay
I installed the hMail server (5.4) but after 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 accordigly. 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,

http://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-resources/smtp-relay-with-office-365/

http://community.spiceworks.com/how_to/show/50057-mail-relay-to-office-365-using-stunnel

In the case that you will have such a scenario this will help you that you do not lose too much time, like me, to figure out a working solutions. It is a little tricky when your application does not support TLS/SSL. I assume that in future all major supplier 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.

 

[driven0]

I'm late to the party but just now dealing with this.

Here is the exact email that we received from microsoft on this problem:

Any user that has UM has to have his mailbox located in the same site, ie if on prem you have to use the on prem UM server, if in cloud, you have to use the cloud UM.

The supported list of SBC’s for Exchange Online UM are available at the following Link:
[URL unfurl="true"]http://technet.microsoft.com/en-us/library/jj673565(v=exchg.150).aspx[/url]

The SBC needs to have an SSL Certificate with a registered publicly available DNS FQDN (the certificate name is case sensitive)
The Office 365 side requires SIP TLS and SRTP to ensure signalling and media are both securely encrypted over the public Internet.

In the end we'll probably get a Sonus for this solution. We're implementing soon, so I'll reply back with our trials and tribulations along the way

 

[Westi]

Did anyone find an easy solution yet that doesn't involve jumping through hoops or relaying the emails?


Joe W.

FHandw, ACSS (SME)


"This is the end of the world, make sure to buy your T-shirt before it is too late"
Original expression of my daughter

 

[holdmusic34]

Yes Westi. Use Gmail.

I'm a Spanish lumberjack and I'm ole'.

 

[Westi]

Holdmusic, I will tell the customer ;-), they just switched and are now not getting emails. The IT guy is not happy but his boss is even unhappier.

I set them up on gmail temporarily but would be nice of they can just use their own.

Joe W.

FHandw, ACSS (SME)


"This is the end of the world, make sure to buy your T-shirt before it is too late"
Original expression of my daughter

 

[AvantiWade]

SMTP Relay is really not difficult to setup on Server 2008/2012 if the customer has an existing server that has space for the service . I setup a GMail address initially because I didn't want to deal with the relay, then setup a smtp relay on a mostly idle windows server VM afterwards to figure it out.

 

[Westi]

thanks AvantiWade
I am dealing with IT people so I hope that they can setup their own SMTP relay server because if anything goes wrong hey blame me for their faulty server.

Joe W.

FHandw, ACSS (SME)


"This is the end of the world, make sure to buy your T-shirt before it is too late"
Original expression of my daughter

 

[qtelcom]

Hello, I thought I'd add to this thread since I had to deal with this.

On release 9.0.3, I could not get Voicemail Pro to send SMTP directly to smtp.office365.com on port 25 or 587 using correct credentials, same problem as the rest of you. Keep getting authentication errors, My understanding is that VMPRO does support TLS, but can't find anywhere to enable it, although from reading other posts, it seems it's just automatic.

Being I couldn't use VMRPO direct to office 365, I did use Hmailserver 5.6.4 B2283 and setup the smtp relay within Hmailserver, HMailServer now does allow StartTLS as an option. So FYI using HMailserver as the SMTP relay to office 365 does work now.