@endlessfix Your multi circle fail was a great test case. I’d run into the issue before and like you, when I redrew it the export would work. I showed Garry the message SimpleDXF generated in the ruby console and he was able to quickly answer our puzzle of a question. His answer also provides the opportunity to point out an important feature of SimpleDXF for those needing to generate g-code, especially for woodworkers.
For SimpleDXF to do its thing it needs to find at least one Edge. My first comment back to Garry was do you mean, a straight line? His response was one of those simple explanations I wish I’d heard 22 years ago when I first started doing CAD + CNC + Wood.
Garry could probably add some code to his SimpleDXF plug-in and solve this slight issue where he requires an edge. That said it might be better for users to understand what’s going on and use this explanation to get more functionality out of his plug-in.
A circle is a circle and an arc is a part of a circle. An edge could be a straight line or it could be a straight line with a bulge. It’s the straight line with a bulge that I’d never understood.
When you use cad geometry to generate g-code directionality is important for cutting direction. A circle has no directionality, only a center point. A straight line, an arc, and a line with a bulge, each have a starting and ending point. The line with a bulge also helps under the hood to figure out directionality. For me it was super helpful when Garry made the point about how a straight line with a bulge is also an Edge.
I was having a hard time with Garry forcing the issue of requiring an “straight line” edge for SimpleDXF to work because there are items we do that don’t have straight lines. But when I remembered how important directionality is and, how he has provided the means of addressing this issue, it’s probably better if we use the feature he has provided to solve the issue of nothing but circles and arcs and the missing edge.
Click to get into the outermost group and then click on the group that holds that largest circle in you failed test file. With that circle selected but not in edit mode click the Start Marker button.
By doing this on a circle you will get this dialog box. Click yes and this will split that circle into 2 arcs. This gives SimpleDXF the single Edge it’s looking for as a requirement. This feature was added for several reasons and it solves this issue you pointed out with your failed test.

After the marker is added you can see how there are now 2 arcs instead of a circle. I realized that in the past when I redrew items and it seemed to work it was because I was manually breaking the circle and then Simple was finding those arc edges without me using the tool Garry had already provided.
If you have multiple circles as in your example and cutting direction does not matter, you only need to add that marker to 1 circle in the drawing where there are no other straight lines or arcs.
@endlessfix see if this works and then you may want to do one of your quick gifs to show others how this works.