I am wondering whether there can be categories where monic arrows cannot be "made left-invertible", by embedding the category into a larger category with the left-inverse.
For example, if I have the category with two objects and an arrow between them (and identities), then of course the arrow is monic, and you can just "add in" an arrow going the other direction to invert it. But I am wondering if this is "always possible" in some sense.
More formally,
Let C be a category. Does there necessarily exist a category D which is a "supercategory" of C (i.e. C is a subcategory) such that every monic arrow of C becomes left-invertible in D and every epic arrow becomes right-invertible?
Or is there a counterexample?

No. Consider the special case where $C$ is a monoid in which every morphism is monic and epic, i.e. a cancellative monoid. If such a $D$ existed, then the subcategory of $D$ generated by $C$ and the inverses of morphisms of $C$ would be a group in which $C$ embeds, since every morphism gets an inverse on both sides. However, by a theorem of Malcev there exist cancellative monoids that cannot be embedded in a group.