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Adding an attachment to an individual feature that is over 500 MB results in the following error (the table name is variable):
Data loaded into attachments must fit into memory. ArcGIS Desktop is a 32-bit application, so it is limited to 2 GB. The memory required for loading must be continuous. So the size limit for an attachment is dependent on how much continuous memory is available. With most configurations this results in a limit around 500 MB per individual file.
Depending on the files being worked with, there may no workaround. However, certain types of files can be handled differently to reduce their size: