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I've two connectors:
1) Dell USB-C Mobile Adapter - DA300
2) Dell WD19 180W Docking Station
& two monitors:
1) Dell P2717H has Display Port cable
2) Dell S2415H has HDMI cable
When either of the above is connected to DA300, then no issues. The monitors work well.
When I connect P2717H to DA300 and S2415H to WD19 then I don't see any display on S2415H even though it is detected in the Displays as shown in the attached.
One more point, the WD19 is currently powering my MBP. So, it doesn't have any issues with connectivity, etc.
Screenshot of Dell S2415H
Screenshot of Graphics/Displays in "System Information"
MacBook Pro 2019 16" with two connectors
