Exchange Server 2019 and Cloud Voicemail Deployment Issues

December 31st, 2018 | Tags: ,

With Exchange and Skype for Business Server 2019 now GA I decided to created a new lab environment, both are Hybrid installations and I opted to create a brand new Office 365 tenant.

For those not already aware Skype for Business Server 2019 (when paired with Exchange Server 2019), no longer has the ability to provide Unified Messaging and Microsoft expects customers to instead leverage Azure or “Cloud” Voicemail. There’s a great table (I’ve stolen from TechNet below) that illustrates supportability across the various versions.

Exchange Server 2013 Exchange Server 2016 Exchange Server 2019 Exchange Online
Skype for Business Server 2019 Exchange Server UM Exchange Server UM Cloud Voicemail Cloud Voicemail
Skype for Business Server 2015 Exchange Server UM Exchange Server UM Cloud Voicemail Exchange Online UM
Lync Server 2013 Exchange Server UM Exchange Server UM Cloud Voicemail Exchange Online UM

The planning and setup is well documented here and I followed this guide without any issues, however when I placed a call to voicemail I was seeing call failures, specifically:

“Failed to route to Exchange Unified Messaging Server”;source=”FE.DOMAIN.COM”



The first thing I checked was the licensing, now Microsoft’s requirement is that at least a single user is licensed for Skype for Business with a Teams license assigned. This new tenant met all the prerequisites, but still voicemail would not route correctly and was being rejected by Office 365.

Next step, I logged a ticket with Microsoft. It turned out that the issue was due to the fact that because no calls had been made between any cloud homed users voicemail had not yet provisioned itself correctly. As a workaround I was asked t0 log into two Teams users within the tenant in question and place calls in both directs. Voila – Cloud Voicemail immediately started working!

I was given the impression by Microsoft support that this is a temporary issue and will be addressed in the near future, in the meantime I’m sharing this workaround with other folks.

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