I have a 2018 Mac Mini running Catalina that I am using headless, via screen sharing on a 2009 vintage iMac running Snow Leopard. The mini has been set up for automatic login, under Users & Groups. However, whenever I try to connect to the Mini via screen sharing, I am still prompted for a password. I don't know if this problem is associated with the Mini or the iMac. Any assistance would be appreciated.
Mac mini, macOS 10.15
Yes, that is normal behaviour. You can see that it is just the screen sharing password prompt, because after entering it the desktop and all open applications (if you have some in login items) will be visible instantly. If it were really logging you in for the first time you would see the desktop build up and applications launching.
I think that is normal behavior when accessing the Mac remotely.
I am using a 2011 Mac mini with High SIerra headless via VNC to my late-2013 27 inch iMac with Apple's Screen Sharing application. I purchased an HDMI dummy dongle that is plugged into the mini and makes it believe it is connected to a external HDMI monitor. When I connect from the iMac, a larger mini screen appears (than would without that HDMI dongle), and I am automatically logged in to the mini Desktop, just as I would be if the mini were physically connected to a real display.
Search Amazon HDMI Dummy plug. Read carefully as some can do 4K and others at lower resolution.
Headless mac mini won't login automaticly
