Voicemail to email - Office 365

Office 365 and voicemail to email relay -  problem is that the voicemail system is old and does not support TLS and the gotcha is you cannot setup a "user" that actually sends the email.
I've setup a simple IIS6 smtp relay on a server 2008/2012 to relay email from a copier/MFP device to O365.  In the copier, I can set a "Sender" and then alias that to the authenticated email on the backend and it works to Office 365.

In this case the voicemail system is so old that each user that get voicemail to email has their own email address listed in the voicemail system.  I cannot add all these users to the IIS SMTP server so not sure the best way to accomplish.

Would direct send work?  Do I create a connector on the Office 365 system and have the voicemail system send to the MX record?

Any suggestions would be great and thanks.
RFloyd30Asked:
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Allen FalconCEO & Pragmatic EvangelistCommented:
Sounds like it is time to upgrade the phone/voicemail system so it works with current communication technologies.  A VoIP system or service can be affordable.

You can probably rig up something with an upgrade, but how reliably will it work and how much time/effort will it take to setup and keep running?
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AmitIT ArchitectCommented:
Office 365 required TLS 1.2 to connect. Without which you cannot connect. It is better you upgrade you phone system, which support TLS. More to read:
https://support.office.com/en-us/article/how-exchange-online-uses-tls-to-secure-email-connections-in-office-365-4cde0cda-3430-4dc0-b489-f2c0736c929f
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Alan HardistyCo-OwnerCommented:
You can send via port 25 to the MX record for your domain that 365 asks you to setup, without TLS encryption enabled, or any authentication and it should work just fine, but you may have to setup a new Connector in 365 to allow emails from your (hopefully) fixed IP Address too and that should allow things to work happily,

Alan
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RFloyd30Author Commented:
Thanks for the replies - of course, upgrading phone system is the ultimate solution but not answers looking for when posting here.  Lots of companies can't just upgrade their phone system at will.  Long term yes but when posting here, we all are looking for fixes and "work arounds" to help get old tech to work with new tech if there is a possible way.

Alan's solution is what i was looking for to confirm other KB articles we are reading.  

Thanks again to all !!!
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