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Export failing due to connection issue

Customers have data exports to the TOTECS platform scheduled to run multiple times a day (Typically Product Stock Quantities export). Data exports to Totecs Platform infrequently fail due to connection issues identified by: -The request was aborted: Could not create SSL/TLS secure channel.( The most common reason) -Error: The remote server returned an error: (502) Bad Gateway. What is the best way to investigate causes of these issues?