How do I return an associated type from a higher-ranked trait bound trait?

Having the closure wrap the return type in a newtype fixes the issue:

#![allow(unreachable_code)]

use std::marker::PhantomData;

trait Endpoint: for<'a> EndpointBody<'a> {}
trait EndpointBody<'a> {
    type Out: 'a;
    fn serialize(body: &Self::Out) -> Vec<u8>;
    fn deserialize(raw_body: &'a [u8]) -> Self::Out;
}

struct EPOut<'a, EP: Endpoint>(<EP as EndpointBody<'a>>::Out);

// /////////////////////////////////////////////////////////

/// Trait object compatible handler
trait Handler {
    fn execute(&self, raw_body: &[u8]) -> Vec<u8>;
}

/// Wraps a function for an endpoint, convertint it to a Handler
struct FnHandler<EP, F>
where
    EP: Endpoint,
    F: 'static + for<'a> Fn(&'a [u8]) -> EPOut<'a, EP>,
{
    func: F,
    _ph: PhantomData<EP>,
}
impl<EP, F> FnHandler<EP, F>
where
    EP: Endpoint,
    F: 'static + for<'a> Fn(&'a [u8]) -> EPOut<'a, EP>,
{
    pub fn new(func: F) -> Self {
        Self {
            func,
            _ph: PhantomData,
        }
    }
}
impl<EP, F> Handler for FnHandler<EP, F>
where
    EP: Endpoint,
    F: 'static + for<'a> Fn(&'a [u8]) -> EPOut<'a, EP>,
{
    fn execute(&self, in_raw_body: &[u8]) -> Vec<u8> {
        let body = (self.func)(in_raw_body);
        let serialized_body = unimplemented!();
        return serialized_body;
    }
}

// /////////////////////////////////////////////////////////

/// Collection of handlers
struct Handlers(Vec<Box<dyn Handler>>);
impl Handlers {
    pub fn new() -> Self {
        Self(vec![])
    }

    pub fn handle<EP: 'static, F>(&mut self, func: F)
    where
        EP: Endpoint,
        F: 'static + for<'a> Fn(&'a [u8]) -> EPOut<'a, EP>,
    {
        self.0.push(Box::new(FnHandler::<EP, F>::new(func)));
    }
}

// /////////////////////////////////////////////////////////

struct MyEndpoint;
struct MyEndpointBody<'a> {
    pub string: &'a str,
}
impl Endpoint for MyEndpoint {}
impl<'a> EndpointBody<'a> for MyEndpoint {
    type Out = MyEndpointBody<'a>;

    fn serialize(body: &Self::Out) -> Vec<u8> {
        unimplemented!()
    }
    fn deserialize(raw_body: &'a [u8]) -> Self::Out {
        unimplemented!()
    }
}

// /////////////////////////////////////////////////////////

fn main() {
    let mut handlers = Handlers::new();
    handlers.handle::<MyEndpoint, _>(|_body| EPOut(MyEndpointBody {
        string: "test string",
    }));

    handlers.0[1].execute(&[]);
}

I'm tempted to say this is a Rust compiler bug, considering that the newtype should be just about the same as the associated type. There also seems to be some ICEs relating to using HRTB associated types: https://github.com/rust-lang/rust/issues/62529