Okay, this may be a dumb question and/or me misunderstanding the rules. But here goes:
The special ability you get as a wizard around level 6 or 7 when you pick enchantment as your spell school makes you able to cast the same enchantment spell on two targets. For instance, dominate person works against two humanoids instead of one, and so on.
The problem is that with the way concentration works in this game (and in the 5E ruleset in general, I suppose), once you cast another concentration-requiring spell, the first one breaks. This means that when I use Dominate Person on two targets simultaneously, one of the targets is immediately un-dominated.
Is this intentional? Is it a bug? If the former, what is even the point of this special ability? I feel like it's quite useless.
And yes, I am aware that enemies sometimes make immediate saves against a spell even when you succeed in casting it on them. I don't think this is what is going on here.
It's fine, you can cast a single spell on multiple targets. It's not supposed to break concentration. If you are casting the spell twice then, yes the second spell over writes the first, but you should have an option once you get to that level 10 as an Enchantment Wizard to cast Split Enchantment and then select Dominate Person and then you can select 2 Targets. It should be in the far right menu next to your spells where Metamagic feats and Spell item abilities would normally be.