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I made a few minutes to take a look at this tonight.  

I do see the behavior you describe, although the order is not the root cause. 

In this line:  github.com/LinuxCNC/linuxcnc/blob/bd9034...ialog_widget.py#L201



it's this part that is causing issue:



The icon value is set correctly to 'WARNING' on the go-in, but because but because icon is of type str, the second condition "isinstance(icon, str)" evaluates to True, and therefore never gets to check for 'WARNING'.

Perhaps it’s meant to be a catch all, in that case I agree it should move to last, but I want Chris to weigh in before I change it as I'm not quite sure of the purpose (if typo should we tell the user there’s a typo?).

Yes, I am using (I used) Virtual Box as VM for test.

Is the NativeCAM path correct in the ini file?
(you could post your ini file)
Is NativeCAM runnig standalone from the command line?

As suggested by HansU, you could try to run LinuxCNC from the command line to see the errors during startup.

Wollongong. Not too far!