Microsoft Licensing Policies Are…Kindof a Bummer

Today I called Microsoft to order some Windows 2000 Terminal Services CALs.

Once I get over just how awkward it feels in 2007 to have to call via telephone to acquire a license in order to let someone access the server in a slightly different fashion (e.g. via Terminal Services), it seems like the mechanics should be simple enough. They actually appear to make it easy for you. Launch the Terminal Services Licensing application and select the menu item that says "Add Client Access Licenses" (or similar), which gives you a phone number and some crazy long License Server ID to give the customer service rep on the other end of the line. This is where it gets interesting…

Dial the number. "Welcome to the Windows XP Activation Service." Huh? Keep listening. "…and I can also help you with Windows Terminal Services Licensing." Finally. What, Microsoft can't afford to dedicate an 800 number to this thing? O.K., step my way through 2 levels of voice tree only to be placed on hold. Wait time was short enough; so far, so good.

"Hello, my name is [REDACTED]. How can I help you today?"

"I'd like to obtain some Windows Terminal Services CALs."

"Please read me the license key."

"You mean the License Server ID?"

"You're wanting to install Terminal Server CALs, correct?"

"Yes, but I don't have the license key yet. That's why I'm calling. I need to obtain them first. It says to call this number to do that."

"Oh, o.k. read me the License Server ID."

"[read really long alphanumeric string over the phone]"

"What is your volume licensing program id?"

"Huh? What's that? We don't use volume licensing."

"O.K., you need to contact the Microsoft Reseller."

"Which Microsoft Reseller? The product says to obtain the licenses from this phone number."

"Oh, please tell me your product ID."

"You mean the Product ID for Windows 2000? I don't have it with me. Shouldn't the License Server ID cover that? I mean, isn't that why you require Terminal Server activation and all that?"

"It should be on the product packaging."

"Right. I don't usually keep the product packaging handy for a product I originally purchased 4 years ago. I'm really going to have to dig that out of wherever to do this?"

"Yes."

"…"

"Thank you for calling Microsoft. Have a great day."

So, now to go dig up the product key and then repeat the process. I'm still confused as to how this model of software distribution constitutes a greater value to small businesses than Free Software. Knowing Microsoft, I'll call back only to be told that Windows 2000 is an EOL product, so I can only buy additional CALs if I spend hundreds of dollars to upgrade to Windows Server 2003. All so that I can let one additional computer interact with this server.