The output raster needs to be saved in a file geodatabase instead of a normal folder. This should stop the unknown error: 999999. The extract by mask script will not work if the save location is not in a file geodatabase.
I found a fix to this error. Just don't change the ArcGIS default output location when running the tool. You can change the name of the output file though. But let it save in the default directory given by ArcGIS (somewhere in User-Documents-ArcGIS-...). And if the default path is something else (maybe a colleague changed it or something) then that is not considered as the default path. It should be ArcGIS defult path in the location I roughly mention above.
the error 9999999 etc is a generic error without a fix ... the best thing to do is to restart arcgis , as for clipping a raster by using a mask save your raster as a .png file because if you are using a .tif raster and say it's a high rez image arcgis goes UMMM... and throws a bunch of errors your way i had the same problem and changing the file extension did the trick
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