That’s a great question. I can’t give a definitive answer, but here’s what I know:

- To clarify, you’re never “purchasing” a typeface; only licensing for use.
- Some type that comes with operating systems or other software is not the best version of that particular face. See: http://www.typography.com/ask/faq.php?faqID=98#Faq_98
- To use, say, Georgia in a PDF, you would need to license either a specific face (Regular, Italic, Bold, or Bold Italic) or the whole family for that specific kind of use; However, using Georgia on the web is free (I suppose a one-time licensing fee was worked out as part of the software price?). You would license Georgia from Ascender:
http://www.ascendercorp.com/fonts/microsoft/

It would be great if someone took an index like Phil Shaw’s Code Style font survey results and linked each of them up to their respective sellers. That way, at least we’d know who to ask if we wanted to use something already on our computers.
http://www.codestyle.org/css/font-family/sampler-CombinedResults.shtml

Thanks for your help Tim.

I’m going to keep looking and I’ll report back when/if I find anything definitive.

Font the following which may shed some light on the subject.

“Are some fonts already licensed?

When you pay for your software application licence for products such as Microsoft Windows, you license the core fonts that are included within that application for the number of users you have licensed that application for.

Software publishers license fonts from foundries and pass on the royalty to the foundries from your licence fee.

This does not give you the right to transfer fonts from that application to unlicensed users or to use those fonts outside the terms of the software licence you have.”

faces.co.uk - http://www.faces.co.uk/corporate_services/font_licences.cfm

According to Microsoft’s ToS for Fonts & confirmed by Simon Daniels of MS typography;

Windows and Office include the following font license…
c. Font Components. While the software is running, you may use its fonts to display and print content.
You may only
• embed fonts in content as permitted by the embedding restrictions in the fonts; and
• temporarily download them to a printer or other output device to help print content.

“That would suggest that you can use them to produce commercial posters and ads and broadcast materials” -Si
But doesn’t include logotyping or branding with the fonts.

For what its worth. I just received an email reply from Ascender - they who manage MicroSoft’s font licensing - to say that fonts included with MicroSoft products should only be used with those products… ?