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As Dana mentioned, unloading and then detaching is not necessary. If you want the xref gone, just detach it. As for the xref not detaching, I have had this happen to me before and the solution was to repath the xref and then detach it. I think if Autocad loses the association to the file, it gets confused and doesn't know what to do, so resetting the file path has worked for me.

Well here is your problem: boundary either creates a region or a pline/lwpline. Difference between pline/lwpline is controled by the var 'plinetype. Change it to 2 (setvar 'plinetype 2), and your boundary will generate lwpline instead of plines. LWpline only have sets of 2 coords in assoc 10, and everything will work as it used to(as long as a boundary can be created successfully of course)! If my reply help you solve your problem, please consider marking it accordingly. Thanks and have a nice week end!

Thanks everyone, problem solved thanks to all of you!

I've got faith in you Chris, you can do. Heck if I can do it ANYONE can Getting the text cleaned up might be the trick. Get that right and you should be good.

Sure, my bad I should have looked 1st at your version. Sean Column Fitting edit r2013.dwg

Multiple references to the same file get auto-named by AutoCad, as in xref-1, xref-2, and so on. They will be listed in the xref dialog individually and must each be detached as if they were different files. IMHO the problem might be that the unload was done first. I can't test this right now at home. Not sure if an unloaded xref can be detached. If your intent is to detach, the unload is redundant anyway,

When I detach a PDF, it disappears from the list. Is it possible that you have other references in the drawing to the same file? That will prevent detaching. You should get some kind of error message when the detach fails.

Ribbonclose will get rid of the ribbon ("ribbon" to bring it back) menubar = 1 to give you back the menu and then find the toolbars you want from the tools section of the menu https://knowledge.autodesk.com/support/autocad/learn-explore/caas/CloudHelp/cloudhelp/2018/ENU/AutoCAD-Core/files/GUID-03F19B49-1DBA-4A99-8DD0-1A63E1E8693C-htm.html