The Enabling Technologies Blog

Our team of Cloud Strategy Advisors, Solution Architects, Engineers and former C-Suite Executives work diligently to provide our vistors with the most pressing information.

Chris Stegh /

The State of Skype and Teams

When Microsoft announced its intent to transition from Skype for Business to Teams, there seemed to be a rough road ahead. The good news is, there have been developments in both platforms, and no major surprises. This article summarizes the state of Skype and Teams as of May 1, 2019

Skype for Business Server 2015 is in mainstream support until October, 2020, at which point it’ll enter extended support until 2025. Extended support means that only security fixes will be provided for free, per Microsoft’s product lifecycle. 

Skype for Business Server 2019 became available in mid-2018. Its mainline support will expire in 2024 and extended support will also remain until 2025. Expect a sweeping push toward Teams between now and 2024. 

Skype for Business Online has had no end of support announcement, although MSFT has stopped selling new licenses of several Skype Online packages. The latest change goes into effect on July 1, at which point SfB Online Plan 2 (Standalone) is discontinued. The good news is, customers using SfB under Office 365 E3/E5 licenses are not yet affected.

The main improvements of Skype 2019 involve a more seamless transition to Teams, including:

  • Cloud Call Data Connector support, which can monitor call quality for both cloud and on-premises users.
  • Streamlined transition of users to Microsoft Teams.
  • TLS 1.2 security support
  • "Cloud Auto Attendant" to answer inbound and dial-by-name calls from the cloud.
  • Meetings First feature (in preview) will allow organizations to use Teams for online meetings, relieving their on-premises infrastructure and trunking.
  • Support for Windows Server 2019 (as well as 2016).
  • Cloud Voicemail support, allowing both cloud and premises users to use Microsoft’s going-forward voicemail service.

When to move to Teams

Many organizations are asking, “Should we upgrade once more on premises, or just move to Teams in Office 365?” What’s the main motivation? If it’s to eliminate on-premises servers, then online is obvious. But if it’s to support a certain use case or promised capability, staying on premises may be necessary. Users can actually have both UXs, but it’s simplest to support only one (especially when using PSTN calling and/or meetings).

The factors of when to move to Teams include:

  • The readiness of users for a transition (if they’re already using Teams for multi-party collaboration, they will have a shorter learning curve)
  • The age of the Skype Server hardware on-premises (if it needs an upgrade now, and you’re not ready for Teams, plan to upgrade to SfB 2019)
  • The current and future use cases (contact center and emergency location services are more robust on premises than with Teams or Skype Online, and support for phones/video devices for Teams varies)
  • What are you currently using which will no longer be supported, including P-Chat servers, XMPP federation, and others. Also, if moving to Exchange 2019 on-premises, Unified Messaging in Exchange is no longer offered. If Exchange UM is in use, a move to SfB Server 2019, Teams, or Skype Online are the options forward.

Upgrading to Skype Server 2019 does require deploying new servers side-by-side and migrating from the existing Skype servers. This contrasts with the in-place upgrade that came with Lync 2013 to Skype 2015. This was because from a back-end perspective, Skype 2015 was essentially a rebranded Lync 2013.

How to migrate to Teams

More than a rebranding, Microsoft Teams is a new cloud-first platform. That’s why Microsoft is plowing most of its development into Teams, and into the options for migrating to Teams.

Organizations on Lync 2013 who are interested in moving to teams have two choices.

  1. Upgrade to Skype 2019 or Skype Online, and make a slow, rather seamless transition to Microsoft Teams.
  2. Encourage users to start using the Team's user interface and deprecate Lync/Skype as a majority of users move to Teams.

When you're on Skype 2015 Cumulative Update 8, then you get the same seamless transition of users to Microsoft Teams as you would if you were on Skype 2019.

While migrating users to Teams is well documented, ensuring they understand and buy-in to the new user interface is trickier. For those using Skype simply for Instant Messaging and making phone calls, Teams’ other capabilities (multi-party co-authoring, guest access, sideloaded apps) may be overkill. End-user change management and IT/legal governance become critical.

Developing Your Plan

Think of your motivation, tolerance for having hardware on premises, and current and future use cases. Mixing these factors together should help point the way.

Enabling Technologies has Collaboration Assessment Services to evaluate your current state and develop a plan for your organization’s future Intelligent Communications platform, whether it be Teams, Skype, or a hybrid. Contact or subscribe to Enabling’s blog for regular updates.


Office 365 Roadmap (search for Teams)

Skype 2019 Announcements:

Teams Annoucements:


Work with our team of Cloud Computing Consultants who have done this so many times they know all of the “minefields” to prevent missteps.