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Andrew I have never heard of this ability and I do try to keep up with what the other vendors are doing. If this is possible someone should be able to tell you how.  The fact Sketch is joined at the hip with the estimating feature in building an estimate area by area it would be my guess you need to start and complete any diagram from within Xactimate and not Autocad but Xactimate may use the Autocad engine.

Just curious??......why go to the trouble of importing a foreign diagram to Xactimate when you'd have to dummy up the estimate anyway?  I haven't used X now for the past couple of years, and maybe the X roof sketch program is functioning better now, but remember always having to tweak the estimate to make it right..  Many roofs I've inspected were impossible to do on sketch.  Hand-drawn with sidebar calculations, and then scanned & uploaded with the estimate.  Might call it old school, but indisputable scopewise.  Your CAD program accomplishes the same thing, but whether you can make it write the estimate is doubtful.  If your examiner doesn't like it, ask them to duplicate the roof diagram on the program just once and see what results they get.  They won't bother you again.