Do you remember the comment in our last blog, Deep Dive: What You Need to Know About Licensing for Windows Server 2012, advising IT leaders to be sure that they can stand by the choices they make to deploy Windows Server 2012 Standard or Datacenter on various systems across their environments? Thinking with the future in mind is the only way to avoid making costly licensing mistakes that initially may seem like good decisions.\nIndeed, taking a forward-looking approach is the difference between simply buying licenses and adhering to a licensing strategy. Being good at the latter proposition requires that IT leaders be highly cognizant of their organization\u2019s trajectory \u2013 whether it\u2019s on a fast growth track vs. keeping pace with the market, for example \u2013 so that the business doesn\u2019t suffer from penny-wise but pound-foolish licensing decisions.\nAs we\u2019ve discussed, the main difference between Windows Server 2012 Standard and Datacenter is in the number of virtual machines supported on the host hardware \u2013 two vs. unlimited VMs per two-processor license, respectively. When an IT leader isn\u2019t thinking strategically about licensing, based on understanding where the business is going, it can become very easy for him or her to fall into the trap of thinking it\u2019s cheaper just to choose Windows Server 2012 Standard for a system that currently maxes out at two VMs in its own little silo.\nThat\u2019s only true, though, as long as that is all that the server ever will do. It becomes one of the most cost-ineffective decisions he or she will ever make, however, if the organization is on a ramp-up curve that is going to require that its infrastructure increasingly be put to work in highly virtualized multi-host clusters.\nTake the example of a cluster composed of four host machines with high availability turned on, with four processors on each host for a total of 16, and with 58 virtual machines. Windows Server 2012 Standard licensing simply wouldn\u2019t scale to suit this without IT spending a lot of money and getting a lot of headaches in return. Microsoft\u2019s 90-day license transfer restriction says that you can transfer a Windows Server license between physical servers only once every 90 days: Because any of these VMs can reside on any one of the physical host machines to which licenses are assigned, and because they move among them as workloads dictate, each host would have to be licensed for the potential maximum capacity of the cluster to stay within scope.\nThat adds up to 116 Windows Server 2012 Standard two-processor licenses \u2013 and every time a new VM is added, two more licenses must be purchased in order to have enough to cover every host machine.\nIn such a case, adopting a licensing strategy built to have close alignment with corporate requirements would lead the IT leader to go with Windows Server 2012 Datacenter from the start. With its two-processor licensing supporting unlimited VMs on the host, only eight licenses of Datacenter would be required to gain 16 processors worth of coverage.\nIt\u2019s never too soon to start developing a licensing strategy for Windows Server 2012 that will work for your enterprise, especially if you need to get more familiar with the licensing impacts of issues such as the 90-day transfer restriction. Three to six months ahead of your next major licensing event should give you a good head start, including allowing for time to discover whether it\u2019s wise to rebalance your licensing scenarios in favor of Datacenter for highly virtualized clusters to actually reduce costs in the long-term.\nDon\u2019t be shy about looking to partners for help in this process \u2013 that\u2019s what they\u2019re there for, after all.\nWith the end of support date for Windows Server 2003 fast approaching, there's never been a better time to plan your data center transformation. Our experts have designed this helpful tool to get you started on the right upgrade path for your unique environment, applications, and workloads.