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Annotation export map to image not working

Question asked by friedcc on Jun 6, 2019

There appear to be issues with Arcpy exporting maps with annotation to PDF, JPG, etc.  Sometimes the annotation gets exported with the map, sometimes it does not.  I have checked the scale dependencies (there are none for the annotation), the fonts (it is just plain Arial), and everything else that I can think of. What is really curious is that if I run the exact same code in the Python window in ArcMap, it does export all the annotation. If I run it outside of ArcMap, it does not.  There are no error messages, or any other indications of issues. This is really annoying and I have spent quite a few hours messing with this.  This is with ArcGIS Desktop 10.5.1 version.