Own ruby extension and SketchUp Pro License

I don’t really think it legally matters where the SketchUp is installed, ie, on the same machine that serves the webpages, on a separate machine connected by a LAN, or on a machine remote from the web server connected by WAN or Internet, etc.,… if the SketchUp application is controlled by people who are not a party to the license agreement under which the SketchUp install in question is used, then it is a EULA violation.

But perhaps the Trimble corporate legal might like the idea, or not care in a particular case, and might give a written variance, or special permission.

It can’t hurt to ask, but you likely have to do so in writing sent to their corporate. I wouldn’t say the chances are good. They probably do not wish to spend a lot of time processing requests like this, nor would they wish to set a precedent.