Same thing happening to me. Whether from wake or on boot, I have to reseat the headphone jack to my external speakers. I just received and activated my Mac Mini 2018 on 12-12-18 and it has done since I first turned it on. I set everything up first, plugged everything in, then booted up. Upon first boot, I noticed that when I tried playing back music from iTunes, I got a No symbol when I tried pressing the volume keys, I reseated the cable, sound started working. Moreover, I left the music playing, as per my settings the screen went to sleep but the music kept playing normally. Upon hitting the keyboard to wake up my Mac mini, the music shut off. I logged back in and reseated the headphone cable to get the sound out again.
Finally, it should be noted that in iTunes, the music playback does not stop. Meaning the Mac mini knows the cable has not been disconnected as with any Apple product I own, playback stops when the connection is purged. This is true with both the wireless connection on my iPhone and physical connections i.e. the headphone jack on my new Mac mini. I hope Apple can fix this with a software update. As of now I plan on using USB audio, so it will not be a problem for much longer whether Apple fixes it or not.
ps. I have tried all the "solutions" suggested by i_rina on this thread, no go.
UPDATE: I all but immediately found the solution after I posted this. This is my first Mac mini and have only had iMacs before, I was not aware that you have to go into the sound preferences and select "External Headphones" from the menu. I made the setting change and but my Mac mini to sleep, woke it, and then tried restarted, each scenario proved this is the fix. I feel dumb.