I am trying to convert multiple feature classes located within a file geodatabase into a CAD friendly format.
Without extracting the files the "Export to CAD" tool does not recognize the feature class.
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If you export your feature classes to shapefiles, you can then bring them directly into CAD. I support a dozen CAD users on a daily basis and 99% of the data I give them are ESRI shapefiles. Assuming your projections are correct, the shapefiles should drop exactly into place in CAD, and will retain their attribute data as well. I'll provide a link detailing the process to import the files with AutoCAD.