Showdown: Office 365 Business Premium or leap for Microsoft 365 Business Edition?

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Showdown: Office 365 Business Premium or leap for Microsoft 365 Business Edition?

Organizations who are moving to Office 365 are always faced with the same dilemma: where to start? What subscription bundle should you buy?  There can be a lot of anxiety produced in this decision making, since there are getting to be so many different choices, and it isn’t always clear if you’re making the “right” decision: what are you leaving behind? Are you paying too much for features and software you will never really use? And of course, cost is always a factor.

As I have pointed out previously, these days, almost all organizations should be looking at a bundle which includes Office software for the desktop. It just makes sense, given the direction of Microsoft’s development (soon legacy versions of Office will not be allowed to access 365 services).  Therefore, subscription-based licensing for the Office applications just makes sense. In the SMB space, some folks will be achieving this through Office 365 Business Premium. And a few will be looking toward the new Microsoft 365 Business plan.

In this article, I want to present an argument that most small and mid-sized businesses should probably be leaning toward Microsoft 365 Business as their defacto starting point. But you don’t have to follow my advice: you can also use this article to make your own decisions, and be aware of what you’re leaving on the table, so to speak, by choosing Office 365 Business Premium instead.

The good news

The first and most important point for you to remember is this:

You can always upgrade your subscription later on down the road. Microsoft is always willing to accept more of your money, and they provide simple ways to upgrade existing subscriptions, even if you pre-committed to a full year and decide to change mid-stride–you can seamlessly switch out Office 365 Business Premium and move up into Microsoft 365 Business when the time is right for you. There will be no re-installation of software required to do so–the only major change you would need to consider is joining your PC’s to the Azure AD domain, once you have the Microsoft 365 Business subscription active and configured.

Note: This is to be contrasted with the scenario where you start using Office 365 E3, and move into the Microsoft 365 Business track later: in that case, you would need to uninstall and re-install Office applications for all of your users, since they are technically different versions (Pro Plus vs. Business). So it is better to start in either the Office 365 Business or Enterprise track, and upgrade to the Microsoft Business or Enterprise plans, respectively from there, whenever possible.

The argument for Microsoft 365 Business

For the money, no better subscription bundle exists today, in my opinion. I will prove this mathematically below. Not only do you get Office 365 Business Premium, but you will have access to some pretty advanced security and compliance products layered on top of it, right out of the gate, and at a massive discount. Archiving will grant your users essentially unlimited mailbox storage, and advanced retention policy capabilities across all 365 data. Advanced Threat Protection (ATP) can mitigate and defend against zero day and spear-phishing attacks. Intune will help you to manage and secure devices. Azure Information Protection provides you with the super-powers of message & document encryption, and rights management. The list goes on. None of these things are included in the Office 365 Business Premium edition, on its own.

Here are the prices for individual add-ons (in USD at the time of this writing) with quick explanation of what they include:

  • Exchange Online Archiving: $3.00/user/month
    • Unlimited mailbox archiving
    • Archive & retention policies
    • In-place and litigation hold
  • Advanced Threat Protection (ATP): $2.00/user/month
    • Safe links
    • Safe attachments
    • Anti-phishing policies
  • Intune: $6.00/user/month
    • Mobile Device and Mobile Application management (MDM and MAM) policies
    • Security Group (SG) targeting for policies
    • Deploying device profiles and security configuration
  • Azure Information Protection P1: $2.00/user/month
    • This feature enables Rights management and Email encryption
  • Data Loss Prevention (DLP): $3.00/user/month
    • Automatically detect and take action to prevent leakage of sensitive data types

The add-ons alone total to $16.00/user/month on top of the $12.50 for Business Premium–and that doesn’t even account for the Windows 10 licensing! Compare this result with the $20.00 / user / month price tag on the Microsoft 365 Business SKU. According to these prices, we might deduce that adding Windows 10 to the bundle results in NEGATIVE $8.50 (MS pays you for Windows 10?).  Now, let’s try doing similar math with the Enterprise editions of the Microsoft 365 SKU’s, just for fun.

Microsoft 365 E3 bundle is 32.00 / user / month, including:

  • Office 365 E3 = $20.00 / user / month
  • EMS E3 = 8.74 / user / month
  • Windows 10 E3 = ???

I guess that means the Windows 10 Enterprise license comes out to about + $3.26 / user / month. And given the giant price tag on Microsoft 365 E5 ($57.50 / user / month), the contrast is even more stark:

  • Office 365 E5 = $35.00 / user / month
  • EMS E5 = 14.80 / user / month
  • Windows 10 E5 = 57.50 – 49.80 = + $7.70 / user / month

Of course, to be fair, the Enterprise subscriptions include Windows Server CAL’s via the EMS license, in addition to the fact that Windows 10 Enterprise is included. But still the fact remains: no other subscription bundle compares on value, dollar for dollar, to Microsoft 365 Business. So what does the Windows 10 Business subscription give you, at (– $8.50) / user / month? Take a look…

  • Windows 10 specific features:
    • Upgrade your PC from 7/8/8.1 Pro to Windows 10 Business edition
    • Enterprise State Roaming for Windows 10 with Azure AD join
    • Remote wipe Windows 10 devices
    • Autopilot: automatically install Office apps on enrolled Windows 10 devices
    • Self-service BitLocker key recovery
    • Windows management, Update, Defender, Firewall policies, etc.:
      • Windows 10 devices kept up-to-date automatically
      • Protect PCs from viruses and other threats using Windows Defender Antivirus
      • Protect PCs from web-based threats in Microsoft Edge
      • Use rules that reduce the attack surface of PC devices
      • Protect PC folders from threats such as ransomware
    • Organizational Controls such as:
      • Turn off Windows tips and advertising from Microsoft
      • Control user access to Cortana and the Windows Store
      • Windows Hello requirements, and device screen on idle

That right there is a pretty good list of features they pay you to use (and since it’s initial release some of these things are new–there are probably more coming).


If you are an organization with security & compliance challenges, then the Microsoft 365 Business subscription bundle should be a no-brainer. Otherwise, one might argue that if the organization does not have this requirement, and is still heavily reliant on old on-premises Active Directory and other Windows Servers, then Office 365 Business Premium might be sufficient for now, with one or two add-ons if needed. Eventually though, you should be ready to switch your Windows PC licensing and management over to the new model–so you might end up in this SKU anyway–although it may be a bit further down the road for you. And just note that you can indeed run this subscription in a hybrid environment.

If you want to see a full service description of Microsoft 365 Business, check this resource out–it includes a nice comparison against Office 365 Business Premium and other products.


Comments (2)

  • Rich Lusk Reply

    Hi Alex. Great article for comparison. I did notice that you have an “x” for Exchange Online Archiving not being included in Office 365 Business Premium. It is included in Office 365 Business Essentials and Office 365 Business Premium as I have enabled it and used it. Maybe when you wrote this article it was not included in Office 365 Business Premium. Has there been anything added to Microsoft 365 Business that can be included in your chart? Thank you for writing great articles and helping us MSPs.

    May 24, 2019 at 12:39 pm
    • Alex Reply

      Actually I could clarify this a little bit. First, yes you can turn on an archive mailbox with Business plans. But that is not what the infographic is refering to here. Exchange Online Archiving is a SKU that you can buy as an add-on to Exchange Online Plan 1. It will open features like litigation hold, or the ability to add archive mailboxes for on-premises (hybrid) mailboxes. So it is confusing because the name of the SKU vs. the features it exposes. I suppose I could change the info graphic to list features rather than SKU’s.

      May 24, 2019 at 2:44 pm

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