Multiple associated type-parametrized bounds fail to resolve

[syntacticsugarglider]

With this source

use core::marker::PhantomData;

pub trait Wrap<T> {
    type Wrapper;
}

fn fail<
    T,
    C: Trait<<WrapMarker as Wrap<T>>::Wrapper>
        + Wrap<<C as Trait<<WrapMarker as Wrap<T>>::Wrapper>>::Assoc>,
>() {
}

fn succeed<
    T,
    C: Trait<PhantomData<T>> + Wrap<<C as Trait<<WrapMarker as Wrap<T>>::Wrapper>>::Assoc>,
>() {
}

pub trait Trait<P> {
    type Assoc;
}

pub struct WrapMarker;

impl<T> Wrap<T> for WrapMarker {
    type Wrapper = PhantomData<T>;
}

I expect both fail and succeed to compile. Instead, fail fails to compile with "E0277: the trait bound C: Trait<std::marker::PhantomData<T>> is not satisfied". rustc is clearly able to unambiguously resolve the type here, not only just in theory as associated types are singly defined for a given parametrization, but in practice as it is able to clearly specify the constraint to be added, indicating that <C as Trait<<WrapMarker as Wrap<T>>::Wrapper is already uniquely resolved.

playground reproduction

[oli-cosmian]

I have encountered a similar problem that I am moderately certain has the same root cause: https://play.rust-lang.org/?version=stable&mode=debug&edition=2018&gist=498ce69469cb1f629f23072bf287d08a