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Welcome to Small Business Server 2008

Eriq Oliver Neale describes the history, features, and limitations of Microsoft Small Business Server 2008.
This chapter is from the book

Midway through 2008, Microsoft announced the release of the latest edition to the Small Business Server family, SBS 2008. The product continues in the tradition of earlier versions of Small Business Server, combining many of Microsoft's premier technologies in an installation that can run on a single server, allowing small businesses with limited budgets to have access to the same technologies that larger businesses use to run their operations. Incorporating Windows Server 2008, Exchange Server 2007, Windows SharePoint Services 3.0, and Windows Server Update Service 3.0, SBS 2008 provides a solid technology foundation for businesses of 5–75 employees around the world.

In addition to the businesses that have been looking forward to the release of SBS 2008, IT professionals around the globe have been anxiously awaiting the release as well. Thousands of technology consultants have built businesses around deploying and supporting Small Business Server products, and they are looking forward to the opportunities awaiting them with new installations and migrations in the coming months and years. This book is geared toward those IT professionals who are new to the SBS 2008 product, but come from backgrounds supporting previous versions of SBS or any of the core technologies in larger environments.

History of the SBS Product

SBS 2008, known by its code name Cougar through its years in the development process, is the latest release of an all-in-one product that, quite frankly, breaks many of the "rules" that Microsoft has established for the products that comprise SBS. Traditionally, Microsoft's best practice has been to have a separate server for each of the key technologies in SBS. In other words, Exchange should not be installed on the main Domain Controller server, and ISA should not be installed on a Domain Controller at all. But the product has been successfully sidestepping those rules for over ten years, combining messaging, directory services, and security tools into a single, affordable solution for small businesses. To understand how the product got to where it is today, a brief history of the development of the product follows.

BackOffice Small Business Server 4.0

In 1997, Microsoft adopted a BackOffice Products suite family name, which was established and better known for a three-server license suite called BackOffice Server 4.0. The family name designated an aggressively priced product bundle combining Enterprise class server applications as a "solution" built on top of Windows NT Server 4.0. Whereas "full" BackOffice (as the three-server suite was known then) was a modestly integrated bundle of CDs, SBS 4.0 was a very ambitious product concept that fully integrated the same diverse suite of products all into one server. By combining Windows NT, Exchange Server 5.0, SQL Server 6.5, Proxy Server 1.0, and Internet Information Server 3.0 onto a single box, Microsoft hoped to challenge Novell for an entry-level server marketplace that, perhaps, had not yet even been born. Shared modem and fax services and a POP3 connector for Exchange were introduced with the product as well, a signal that small business customers needed familiar problems solved as part of the solution suite.

SBS 4.0, as it came to be known, was limited to a maximum of 25 users, and had some initial deployment issues. Only Windows 95 and NT clients could connect (not Windows 98), and many of the wizards that handled management of the server would routinely crash. But the release of SBS 4.0a (effectively SBS 4.0 SP1) addressed many of these issues by including Internet Explorer 4.01 for both the server and the clients, and the management tools were updated to work with the added functionality in IE 4.01.

For the first time, small businesses were able to use the same tools that larger companies used for messaging, security, and application support. Outlook 97 enabled employees to have their e-mail, calendar, and contacts stored in a central, protected location, and users could easily share calendar and contact information through the Exchange server. Proxy Server helped increase Internet performance by caching Internet traffic on the server for commonly-accessed web sites. SQL Server 6.5 allowed businesses to look at using a wider variety of line-of-business applications that relied on SQL as a back end, because they did not have to take on the cost of a separate SQL Server license with the product.

The BackOffice product family also introduced the unified Client Access License (CAL) concept that continues with the SBS product today. Instead of purchasing a separate CAL for each of the Windows, Exchange, SQL, and Proxy Server components, SBS customers purchased a single CAL per seat. The unified CAL allows access to each of the technologies in the SBS deployment, and the CAL was (and remains in current versions) priced at a lower cost than purchasing each of the other CALs individually. For this reason, SBS is established as the longest-standing product from Microsoft with a technology enforced CAL license manager.

BackOffice Small Business Server 4.5

Microsoft released SBS 4.5 in May of 1999. Still based on Windows NT 4, SBS 4.5 included significant updates to the other technologies bundled with the previous version. Exchange 5.5, IIS 4.0, Proxy Server 2.0, and SQL Server 7.0 rounded out the component updates. For the client side, SBS 4.5 bundled Internet Explorer 5.0 and Outlook 2000, and included FrontPage 2000 as a tool to modify the web content hosted on the SBS server. Another significant change was the increase of users from 25 to 50.

Recognizing that the communications landscape was changing, the Internet Connection Wizard in SBS 4.5 added support for routers and direct Internet connections in addition to modem support. Proxy Server 2.0 offered some control and protection from the Internet, now that many SBS servers would be connected to the Internet full-time instead of connecting as needed.

New management services were added to enhance the ability of the server to e-mail or fax system status information to designated recipients. The ability to select different locations for shared folder paths was also introduced in this version.

The growth and maturity of the product gave the marketplace reason to embrace the product line for use in small businesses and an anticipation of future versions to see what new functionality would be added.

Microsoft Small Business Server 2000

Released in February of 2001, SBS 2000 was a significant departure from its SBS predecessors. In more than just the change of the name (shedding the cumbersome BackOffice label), Microsoft stopped development of the "full-BackOffice Suite" following BackOffice 2000 because SBS 2000 was successfully able to define an identity uniquely and specifically oriented to the small business marketplace and technology goals.

Based on Windows 2000, which introduced Active Directory to the SBS product line, the entire component product line was updated to include the current technologies of the time. With SBS 2000, Microsoft developed the model that future builds of SBS would follow. Once the core operating system was released, the SBS team followed the OS release by about six months, making sure that the available technologies all worked together, in harmony, on the same box. SBS 2000 included Exchange 2000, IIS 5.0, SQL Server 2000, and the new ISA Server 2000. Client tools included IE 5.0, Outlook 2000, and FrontPage 2000, the same as SBS 4.5. The maximum number of users remained the same.

System status information collection and reporting also significantly improved in SBS 2000. Health Monitor was better able to collect and report status information, giving system administrators a better way to keep tabs on the health of a server.

Another significant introduction to the product line with SBS 2000 was the ability to run Terminal Server in Application Mode on the SBS 2000 server itself. This enabled users to remotely connect to the network and run applications on the server just like they would on their workstations.

Many in the community started to question the overall security of the server with SBS 2000, given the ability for "normal" users to log in on the server via Terminal Services, and that the server could be directly connected to the Internet, even with ISA 2000 acting as the gateway. Some of these security concerns would start to become factors in the development of future versions of SBS.

Microsoft Small Business Server 2003

Released in October of 2003, SBS 2003 gained worldwide notoriety almost immediately. Built on Windows Server 2003, SBS 2003 also included Exchange 2003, IIS 6.0, and Windows SharePoint Services 2.0. Client technologies included Internet Explorer 6.0 and Outlook 2003. A new web technology, the Remote Web Workplace, was introduced with SBS 2003, not available in any other Microsoft product, and continues to be one of the most sought-after technologies from Microsoft. The maximum user limit was raised to 75 from 50, meaning that SBS could be used in even larger organizations, particularly if you consider agile use of a combined mix of "per seat" and "per device" licensing, which SBS 2003 adopted.

SBS 2003 also introduced editions of the product, now available in Standard and Premium Editions. SBS 2003 Premium included all the technologies in Standard, plus SQL 2000, ISA 2000, and FrontPage 2003. The price for Premium Edition remained very close to the historical pricing. Yet a key factor in the dramatic adoption of SBS 2003 was the significantly lower price, placing the Standard Edition at half the cost of Premium Edition, and well below the price of just Windows 2003 Server itself.

Despite all the improvements in the product, several aspects of the product generated discord in the SBS reseller community. Many VARs and product users were upset about the split of the product into two editions, especially because they were going to be paying significantly more to keep all the same functionality that they had with SBS 2000. For security reasons, SBS 2003 also removed the Terminal Server in Application Mode functionality, intending for that functionality to be replaced by the Remote Web Workplace's ability to connect to workstations inside the network from offsite. SBS 2003 had also hoped to ship with updated versions of both SQL and ISA, but product delays kept both of those updates out of the initial release. ISA 2004 was later included as a no-cost upgrade for owners of the Premium Edition when SBS 2003 Service Pack 1 was released in July of 2005. SQL 2005 Workgroup Edition was included as part of the Premium Edition of SBS 2003 R2, which was released in July of 2006.

Still, SBS 2003 was very well received by the small business community, and product sales reflected that. The security improvements in the underlying technologies made SBS 2003 a very stable product, which was needed, given the five-year gap until the next major release of SBS. The product contained greatly improved management tools, aimed at giving the business owner, who might not have a technical background, the ability to perform basic ongoing maintenance on the server. Partnering with OEM vendors, the "15-minute" install was developed and marketed for the product, again appealing to the do-it-yourself business owner who could buy a server from a vendor with SBS 2003 pre-loaded and have a working network after answering a few simple questions during the scripted setup process.

Essential Server Solution Family

On February 20, 2008, Microsoft announced the Essential Server Solution family of products, which includes Small Business Server 2008. The other product announced in the family was the return of a "big brother" to SBS, Essential Business Server 2008. Unlike the birth of SBS as a scaled-down "baby-BackOffice" server, EBS 2008 is building upon the concepts proven in the evolution of SBS, extended and adapted for the demands of a medium-sized business. EBS 2008 is a three- or four-server solution that can be managed and maintained using a similar set of deployment and administration wizards, similar to the SBS product. EBS 2008 splits the Exchange 2007 services onto a dedicated server, and includes an Edge server that runs a special version of ISA to provide protection from the Internet. EBS also has Standard and Premium Editions, with the Premium Edition including the ability to run SQL Server 2008 on a fourth server on the network. EBS therefore provides a suite of applications bundled with the related Windows 2008 Server licenses for the designated number of servers.

The basic framework of SBS 2008 was also released on that date, including the move of SBS from the traditional single-server solution to an optional two-server license implementation with the Premium Edition. Table 1.1 details the differences between SBS 2008 Standard and Premium Editions.

Table 1.1. SBS 2008 Editions




Windows Server 2008



Exchange Server 2007



Windows SharePoint Services 3.0



Forefront Security for Exchange



Windows Live OneCare for Server



Second copy of Windows Server 2008


SQL 2008 Standard Edition


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