Things Change.. Butters is now getting a 392

No Bolts Left Behind on YT had an issue with the oil pressure on his 5.7 swap and it turned out to be the wrong pickup. I guess the tab is clocked differently between a VVT motor and no-VVT motor and he had the wrong one so it didn't bolt down square and allowed for a leak. Based on your picture, doesn't look like that is your issue, but maybe the o-ring got kinked or cut during installation?