Migration path from SBS to Office 365 & Windows Server 2016Alex Fields
So many small businesses adopted Microsoft’s Windows Small Business Server (SBS) product–now that the product has been discontinued, these organizations tend to need a little more guidance regarding the migration path forward from SBS 2003, 2008 or 2011.
Do I still need an On-premises Windows Server?
With the option to move most SBS Server functions like Email and file sharing into Office 365 with Exchange Online, SharePoint Online & OneDrive for Business, many small businesses ask whether an on-premises server is still necessary.
I typically recommend keeping a server on-premises, yes, even with Office 365. But in very small offices, you might just go with a hosted deployment of Windows Server Essentials in the Microsoft Azure cloud, instead. Either way, I see a hybrid deployment of Windows Server + Office 365 as the gold standard for the foreseeable future. Here’s why:
- Active Directory Synchronization: Office 365 can integrate with your existing Active Directory domain to provide an easy migration path and smoother transition into the cloud. Single sign-on, and centralized management of users & groups across on-premises & cloud domains is another benefit. Some Active Directory services just are not available in the cloud at this time; Azure Active Directory Domain Services still has severe limitations that do not yet offer a clear migration path from on-premises AD, so an on-premises Active Directory server is still of benefit.
- Device management: Windows Server gives you the best tools for managing Windows devices such as group policy, and that level of control just is not available in Office 365 (but you do get some nice Mobile Device Management features included).
- Toxic data: Every organization tends to have at least a little bit of uber-sensitive data, that they do not want even accidentally shared outside of the organization (or even beyond certain boundaries within it). Azure Rights Management can help mitigate this risk even in the cloud, but for maximum control, you can keep toxic data sets on-premises, and still protect them with Rights Management, if so desired.
- Latency tolerance (and other technical limitations): Certain file types (like databases) are not supported in SharePoint, and very large files can be cumbersome to use in the cloud. The reality is, some apps & data behave better on a Local Area Network (LAN).
- Line of Business application support: Certain software vendors will not support storing file libraries or other dependencies in a cloud such as Office 365. You may or may not be okay to run them in a Microsoft Azure virtual machine. It is best to verify the solution with your official support channels before migrating.
For all these reasons and more, Windows Server still has a place in the small business network. The good news is, hardware is pretty cheap these days, and most small businesses will be able to offload the vast majority of their data footprint into the cloud, meaning that hardware requirements probably have gone down since the last refresh cycle.
Windows Server: Essentials or Standard?
In general, I recommend purchasing and installing Windows Server Standard edition (not Essentials), enabling the Hyper-V role, and deploying a Windows Server Standard virtual machine as your “replacement” server for SBS. Optionally, you can enable the Essentials Experience role, if you are interested in some of the features it contains like Client PC Backup, Remote Web Access, etc. Here is a quick comparison of the two deployment options:
Image credit: itpromentor.com, adapted from this source
The main advantages to purchasing Standard over Essentials relates to scale–do you need to be able to support:
- more than 25 users?
- more than 50 devices?
- more than a single virtual machine?
If yes to any of the above, go with Standard. Otherwise, if you are sure the answer is no, you can probably stick with Essentials.
Note: Windows Server Standard technically supports unlimited users & devices as long as you own sufficient CAL’s, but the Essentials Experience features will only support up to 500 users / 500 devices in 2016 (increased from 100/200 in 2012 R2).
The other flexibility afforded by Standard is being able to join the Essentials computer as a member server, without promoting it to the role of Domain Controller–perhaps less of a concern for some organizations. Of course, you can also choose to switch to Standard licensing down the road.
Office 365: Which plan should I choose?
This is the best resource I know of for comparing the various Office 365 plans and what features they contain.
Many small businesses will go with the “full boat” of Office 365 features, including Exchange Online for Email, SharePoint Online/OneDrive for file sharing and document collaboration, Skype for Business and all of the Microsoft Office applications. In that case, you might be looking at one of these two plans:
- Small Business Premium ($12.50 USD/user/month)
- Office 365 E3 ($20.00 USD/user/month)
I’d recommend supplementing either of these with Exchange Online Advanced Threat Protection (ATP) for $2.00 USD/user/month–this will help guard against emerging & zero-day threats. The big difference between these two plans is that E3 contains more advanced Enterprise capabilities like information rights management, email encryption, litigation hold (usually an important feature for law firms), data loss prevention and others. Therefore, I generally recommend the Enterprise track for the best features and experience.
Image credit: Microsoft
What if I just want Office 365 for Email?
If the Enterprise stuff is just too fancy for you, or if all you really need is Exchange Online for email, then there is an Exchange Online only plan as well, available for $4.00 USD/user/month at the time of this writing. However, you might consider supplementing this plan with some of the following add-ons:
- Advanced Threat Protection (ATP): Protect against emerging/zero-day threats with Safe Attachments & Safe Links; $2.00 USD/user/month
- Exchange Online Archiving (EOA): Add unlimited email archiving; $3.00 USD/user/month
- Azure Rights Management (RMS): Secure your email with IRM templates & email encryption–not necessary if you choose an EMS subscription; $2.00 USD/user/month
- Enterprise Mobility Suite (EMS): Azure AD Premium, Intune for Mobile device management and Azure Rights Management for IRM templates & encryption options; $8.75 USD/user/month
Will Office 365 be compatible with my Line of Business applications?
The other caveat here is that certain Line of Business applications may not integrate with the Office 365 versions of the Microsoft Office suite (Word, Excel, etc.). This is becoming less and less of an issue these days, but it is definitely something to include in your checklist. Therefore, in some cases, you may need to stick with a lower level of licensing such as Office 365 Business Essentials or E1–which do not include the desktop apps. In that case, you’d have to purchase Office apps and any desired extras separately.
Another sticky point for some customers: it can be difficult to combine the Office 365 “click-to-run” desktop applications with other Microsoft applications, for example previous versions of Microsoft Visio or Project. This is obviously frustrating, and something else to have on your radar. Some customers may be eligible for a free upgrade to resolve these compatibility issues.
Recommended Migration Path
The most common migration path for parting ways with your legacy Small Business Servers is the following:
- Migrate Email from SBS/on-prem Exchange server to Office 365 Exchange Online using either:
- Migrate Companyweb / WSS to Office 365 SharePoint Online
- Migrate personal/redirected Documents folders to OneDrive for Business
- Migrate Active Directory/DNS and DHCP roles to Windows Server Standard/Essentials Experience
- Migrate company-wide printer & file shares to Windows Server Standard/Essentials Experience
- Migrate Remote Access (if applicable) to Windows Server Standard/Essentials Experience
- Properly remove Exchange Server from the SBS server
- Decommission the SBS Server (& other legacy servers)
After the migration tasks are complete, don’t stop moving! Office 365 has so much to offer in every area from productivity to security & compliance. Enable online Email archives, deploy Skype for Business, activate Azure Rights Management, turn on Multi-factor authentication and Mobile Device Management–the list goes on. Great new capabilities are right at your fingertips, and they are pretty easy to implement, so don’t be shy about trying them out–your competition certainly is.