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Create Searchable PDF Map in ArcMap

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I am working on a project that requires me to convert several maps to a searchable PDF file. The map is a basic ownership map with boundary lines (polygon shapefile) and owner name (annotation). When I export the file as a pdf with the option to "Embed All Document Fonts" checked I get an interesting result. I would say about 70% of the annotations are searchable in Adobe Reader. I cannot determine why some annotations work and some don't. Angle, text, color, size, font do not affect the outcome.

I tried to export the map as a .tif and use the Adobe OCR feature but that did not work at all. Even with the very clear and simple title block.

Anyone have any ideas or suggestions? This is one of those little things that is driving me absolutely crazy.

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