Skype for Business is looking like a complete ecosystem – software products covering all platforms. Desktops, laptops, phones, tablets, cloud. “Unified Communications” seems to have given way to “Universal Communications”.

Businesses have a real choice for their VoIP phones, chat, conferencing, etc. these days. If you’re going with Skype for Business, you have a decision to make – Skype for Business Server, or Skype for Business Online?

Feature Comparison

In the past, Lync Online had limits. It was missing PSTN connectivity, Enterprise Voice features & Persistent Chat.
Why Doesn’t Lync Online Include Persistent Chat? 4 Reasons
Reader Question: Call Transmission in Lync Server vs. Lync Online

That’s changing with Skype4B Online.


Baked-in Enterprise Voice and PSTN Connectivity are coming with Skype for Business Online’s rollout. Which makes Skype4B Online into what many people originally thought Lync Online/Office 365 would become: a full-fledged cloud-based communications platform. UC as a Service.

Lync Online to Become Full-Fledged Hosted UC Service – NoJitter

Feature-wise, this makes the two Skype for Business platforms are very similar. Add in Exchange Online and your users may not be able to tell the difference.

Skype for Business Service Descriptions (Server and Online) – TechNet

The Differences: Support and Scale

All that said, I still think there’s even more value to Skype for Business Server 2015. You have more control over support, features unique to the Server version…and there’s the question of scalability.

Scaling up on Office 365 is pretty easy – have more users? Buy some more Business or Enterprise licenses.
(Note: Skype for Business Online is available with Office 365 Business Essentials, Premium, and Enterprise E1. But it doesn’t have PSTN capability at these levels. If you want to make calls out, you’ll need the ProPlus or Enterprise E3 levels.)

However, you’re paying more every month for users this way. You don’t with Skype for Business Server – you instead buy a one-time CAL, add users in Active Directory & enable in Skype4B.  (Thanks to Brad for the CAL reminder, below.  I’ll come back to this topic.)

Remember how I mentioned Lync Online didn’t have Persistent Chat? Turns out Skype for Business Online won’t get it either.

According to this plan comparison, Persistent Chat and dial-in audio conferencing are only available in Skype for Business Server 2015. (Enterprise Voice functionality is listed as server-only too, but the NoJitter article talks about Microsoft phasing Enterprise Voice into Skype for Business Online over time.)

I’ve said before that I’m a big fan of Persistent Chat. So this news really disappoints me. Skype for Business Online users are missing out here. Server users aren’t.

Finally, support. All Office 365 plans include phone & web/email support from Microsoft, plus the Office 365 Community. However, if you still need support beyond this, you’ll have to pay for either Premier Support or work with a Microsoft Partner.

Server 2015 support has similar options – Microsoft’s knowledge base, standard Microsoft Support, and working with a Microsoft Partner for advanced support needs.

Either way, you’d end up working with a Microsoft Partner (like us!).

Which Version to Use, by Business Size/Type

All that said, here are my recommendations for who should use which version of the Skype for Business product.

Skype for Business Server 2015:

  1. Enterprises
  2. Multi-Location businesses
  3. Cloud-Cautious businesses (security & uptime are critical, or you must keep data in-house due to regulations).
    1. A hybrid environment is also possible. We’ll discuss these options in a later post.
  4. Businesses who use (or want to use) Persistent Chat, Dial-In Audio Conferencing & E911.

Skype for Business Online:

  1. Small businesses without an Exchange Server
  2. New businesses/startups (until the company grows)
  3. Organizations using a group of online communications tools already – WebEx, Join.Me, Jabber/Google Talk, HipChat

(I reserve the right to modify these recommendations later, as we see more of the rollout!)

While cloud-based services definitely have value – we host our own private cloud for customers, in fact – there’s still plenty of case to use an on-prem version.

Which Skype for Business product are you considering? Please comment or email with your thoughts and reasoning.

Which Skype for Business Product Should You Use?

3 thoughts on “Which Skype for Business Product Should You Use?

  • May 13, 2015 at 8:10 pm

    “However, you do have to pay for more users this way. You don’t with Skype for Business Server – just add users in Active Directory & enable in Skype4B.”

    This is misleading. Lync Server and Skype for Business Server are not free. Users require a CAL. Enterprises with a Microsoft Enterprise Agreement (EA) have it rolled in to their Core/Enterprise CAL suites, but to call it free is misleading for companies not making use of EA contracts.

    • May 14, 2015 at 7:11 am


      Fair point. My statement is overly simplistic here. You’ve also brought up an important point for expounding upon: CAL structure for Skype for Business. Thanks for bringing it up.

  • December 20, 2016 at 11:15 am


    Is there incompatibility issue when stablishing communication between organization using SFB Online vs on Premise? We are using online however we cannot reach contacts outside our organization that use on Premise.
    Is there any additional set up needed on each side?
    MS support is not helping us at all with this…




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