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I do not know who told you that, but MS are pretty clear on what you can and cannot:

  Internal use licenses are for use in a production environment for general internal
  business purposes and not for any type of commercial purpose. For example, installing
  the Windows Server operating system and Microsoft Exchange Server to set up an email
  system that you can use to send business-related email is acceptable. However,
  production use for external commercial purposes, such as hosting a commercial website,
  is outside the scope of these rights. 

  Customer demonstration licenses can be used for demonstration purposes only by partners.
  Sales and marketing employees of the organization can use this software to showcase
  products to your customers, but demonstration products cannot be installed on customer
  hardware or infrastructure and must be used with partner supervision.

  Internal-training licenses can be used for training internal employees only. These
  licenses cannot be used for customer training or for any commercial purpose.

  MSDN subscriptions allow designated employees of your organization to use the available
  software for the design, development, testing, and demonstration phases of application
  development.



Can you install JIRA on that copy of windows 2008 server R2 and access it via VPN?

Straight away we have ambiguity.

Can you run your staging site on it for demonstration purposes?

More ambiguity.

All it takes is a small mis-step.


    Can you install JIRA on that copy of windows 2008 server R2 and access it via VPN?
Depends on what version of JIRA you're talking about. As long as it's supporting your product, be it purely internal (project management) or customer related (issue tracking and CRM) I'm pretty sure it falls under the first paragraph. Note that it states internal business purposes, not on site use only. CRM is not "commercial purposes" in it self, and resembles email example.

    Can you run your staging site on it for demonstration purposes?
It clearly falls under the second paragraph.




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