I use a statistical software package that generates output apparently with the Courier New font typeface. It makes tables of data analysis. The software company allows me to print and make copies of the output for my students, but would the use of the font in this "creative" way by the software be something I would need to check with the font creator about before making copies?
To be sure I understand the scenario, is this your question: "The software maker tells me I have the right to generate both computer-screen and paper versions of the typeface, but what if it's lying to me? What if the software maker only has a license from the font maker to make computer screen copies of the typeface, but did not license the right to make paper copies of the typeface, and so can only convey to me the right to replicate the typeface on my computer screen, but not convey to me the right to make the paper copies?"
Ever heard of the phrase, "don't borrow trouble"? Heck, if that's your worry, I'd also be worried that the software maker is causing you to be infringing when the typeface first pops up on the computer screen, too. If they lie about one thing, they're probably lying about all of it. Dirty rotten scoundrels!
In any event, assuming you're in the US, note US law generally does not permit copyright in typeface, so this is likely a moot discussion.
See e.g. sub-part (e) of this section linked below of the code of federal regulations. Note this is a prohibition against copyright in the actual typeface itself. Computer code required to render the typeface may be subject to copyright. But running off paper copies (your concern) is not making copies of the computer code.http://www.loc.gov/cgi-bin/formprocessor/copyright/cfr.pl?&urlmiddle=126.96.36.199.188.8.131.52&part=202§ion=1&prev=&next=2