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Like @SLW210 I think you would be better off with a Windows Intel PC. Other CAD software that has MAC software is often reported as having niggly problems. Until there is a true MAC OS based say Autocad those problems may continue, in saying that there are some true MAC CAD programs out there. Autocad MAC has existed for like 30 years and still no true native version.

Here is the result of the AECLINEWORKSHRINKWRAP in Archtecture. Engine Part Assembly_ArchSWrap.dwg

@SLW210 Here you go. https://forum.bricsys.com/discussion/40003/extract-outer-boundary-of-2d-drawing#latest

You have to purchase Civil 3D, Architecture is free with AutoCAD. OP still hasn't stated what CAD they are using.

$119 USD, you get 15 day free trial. Most examples didn't show gaps, but looks like the user guide claims Auto Tolerance and Auto island detection. Could you link the discussion on Bricscad for the OP?

AutoCAD for Windows has more features than AutoCAD for Mac. Compare Features: AutoCAD for Windows against AutoCAD for Mac

I think this is the product BIGAL was referring to.https://engenext.com/pages/egboundary.html I have no affiliation to this product, I just remember seeing it discussed on the Bricscad forum.

@SLW210 CIV3D has Shrinkwrap also. Pity they did not include for plain Acad. If you can work out which dll or ARX may be able to copy correct files to plain Acad. As "TotalBoundary " is no longer available there was a post for a similar product may have been here or at Forums/Autodesk. I remember asking how much but did not get an answer. Try googling.

I think I have a solution but would need a test drawing.

I did find this... Lisp to create a boundary around blocks that are not touching. - AutoLISP, Visual LISP & DCL - AutoCAD Forums I should have also mentioned that AutoCAD Architecture FREE toolset has the AECLINEWORKSHRINKWRAP command.

I had to stop on the newer version yesterday due to my "paid" for work, still debugging it. Can you post an actual .dwg of that example for testing? Also, what version of AutoCAD are you using?

I updated something that makes multiple boundaries but cant find the post right now. doesn't work with gaps so idk if its something you could use. lee mac has an outline but also don't think it works with gaps. https://lee-mac.com/outlineobjects.html