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How to License Skype for Business Going Forward into 2016

By January 19, 2016September 11th, 2020Blog, Microsoft, Skype for Business

Microsoft’s Office 365 E5 offering now allows organizations to license their entire user base for Skype for Business with Enterprise Voice and Conferencing without needing any additional hardware on premise, something companies have been salivating over for years. While many organizations are looking to either implement Skype for Business Voice in the cloud for the first time or migrate their on premise solution to Microsoft, there are still many organizations that are interested in installing / keeping their Skype for Business / Lync environments on premise.

The Office 365 E4 sku ($22/user/month), which currently licenses users for Enterprise voice on premise will be discontinued on June 30th, 2016 leaving organizations to change their licensing model or their architecture for Skype for Business. Below are a few options that organizations can take, and should start planning on now.

Remain On Premise – License with E3 & Skype for Business Plus CAL’s & SfB Server Licenses

The Office 365 E3 subscription ($20/user/month) provides the user with all of the functionality that the Skype for Business / Lync Standard and Enterprise CAL’s provide, and therefore they simply need the Plus CALs to gain Enterprise Voice functionality. This may be the right route for organizations looking to remain on premise for two or more years and therefore get the full ROI from the capital investment for those CALs and existing infrastructure (gateways, servers, server licensing, etc.). Organizations would have the option of going with Software Assurance for those CALs to ensure that they are always licensed for the newest edition of the server and client editions.

Remain on Premise – License with E5 & Skype for Business Server Licenses

The Office 365 E5 subscription ($35/user/month) provides users with all of the functionality of the Skype for Business / Lync Standard, Enterprise, and Plus CALs, as well as additional functionality. The local servers still need to be licensed, and SIP connectivity would need to be purchased by a certified SIP provider, but wouldn’t need the additional add-on for PSTN Calling ($12/user/month for domestic calling and $24/user/month for both domestic & international). This option may be enticing for organizations that prefer the OpEx model over CapEx and can see the benefit of the additional features that come with E5 compared to E3.

Migrate to Cloud PBX – License with E5

By moving to the purely cloud option with full E5 integration, companies can eliminate their entire on premise Skype for Business environment and use the infrastructure provided by Microsoft. This would be an entirely OpEx model and would put management of the environment on Microsoft’s shoulders, providing the maintenance and updates to the SfB environment throughout perpetuity. This is an enticing option for companies looking to go fully cloud and reduce internal management costs.

There are additional options and Chinese-menu type approaches for licensing Skype for Business / Office 365, and PEI assists organizations in understanding the differences from a cost/benefit standpoint, as well as integration and migration assistance. If you would like to better understand how Skype for Business could be a business differentiator for your organization, please give us a call at (303) 974-6881 and we will help explain the options available to you.

Martin Feehan, PEI


  • Suresh says:

    Hi Martin,

    Thanks for this article. I have a query.
    My current set up is that my Skype is on premises and Having E4 license for O365. The CAL for skype is part of O365 E4 and therefore no separate CALs bought.
    If i move from E4 to E3, all the features i had in E4 will still be available? Skype consists of Enterprise voice users also.

    • Hi Suresh,

      You’re very welcome! If you move from E4 to E3, your subscription will cover the Skype for Business Standard CAL and the Enterprise CAL, but will lose the Plus CAL, which covers the enterprise voice functionality.
      In order to cover the Plus CAL without needing to upgrade to E5, you have two options. The first option would be to purchase the Plus CAL through Volume Licensing, which would be the capital expenditure approach.
      If you would like to keep the operational expenditure approach, you will need to purchase the Skype for Business Plus Add-On subscription through Office 365. If you leverage CSP/MPSA/EA for licensing, you need to request this license through your licensing partner.
      If you manage your subscriptions directly from the Office 365 admin portal, you would go to Billings > Subscriptions > Skype for Business Online (Plan 2) and go to the Add-on subscriptions tab. This will bring up three options, which you will want to purchase the Skype for Business Plus CAL ($2/user/month) for all users that leverage Enterprise Voice. Your E3 subscription covers the Skype for Business Online (Plan 2) license, so you will simply keep the parity in price that you’re currently paying for E4.

      I hope this helps!

  • Benjamin. says:

    Thanks very much for this summary information.
    I have been looking for such summary for awhile now.

  • Star says:

    I switched subscription from E4 to E3 and purchase a Skype for business plus cal. How can I assign the Skype for business plus cal license.? Should I just toggle on the license to one of my o365 users. However the skype for business plus cal does not appear when I click on edit product license from one of my users.

    • Adam Lee says:

      Hello Star – an answer from PEI’s Engineering Team: “The Plus CAL doesn’t get assigned as it is not an Office 365 license. It is just a standard Microsoft CAL. If they are using SfB on-prem then they are done and really don’t have to do anything. There is a Skype for Business Online Add-on license for $2/user/month which is called the Skype for Business Plus Add-On licenses. This gets the functionality of the Plus CAL that is the OpEx version of the Open Business CAL. ” I hope this answers your question. If you would like to discuss this more in depth with PEI’s team feel free to call us @ 303-974-6881 or email us at Thanks! – Adam Lee (PEI) — UPDATED

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