Most of the feature classes that I overwrite are derived from a SQL database but I’ve also experienced this overwrite issue with File GDB features and shapefiles. Working with ESRI Customer Care/Tech Support, I was instructed before overwriting any web layers, you need to clear the cache and cookies from the web browser you utilize to interface with AGOL. I use Mozilla Firefox. This process wasn’t necessary prior to TLS Security Protocol v1.2 going into effect. Clearing the cache and cookies worked for a couple of web layers but didn’t work for others. I have experienced the issue when overwriting a single feature web layer and a multiple feature web layer.
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