Hi Jonathan, This is unfortunately a bug at 10.2, and has been logged, #NIM093766: When uploading to My Hosted Services, arcpy.UploadServiceDefinition fails with error "000732 Server: Dataset My Hosted Services does not exist or is not supported".]. The severity of the bug has been marked as High. The only workaround at the moment is to manually upload the service. Hi - did this fix make it into 10.2.2 release? Just checking....
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