diff --git a/mockall/tests/mock_return_dyn_trait.rs b/mockall/tests/mock_return_dyn_trait.rs
index 6011791c..ae6ba077 100644
--- a/mockall/tests/mock_return_dyn_trait.rs
+++ b/mockall/tests/mock_return_dyn_trait.rs
@@ -10,6 +10,23 @@ trait T: Debug + Sync {
 }
 
 impl T for u32 {}
+trait Base {
+    fn as_t(&self) -> &dyn T;
+}
+trait Derived: Base {
+    fn as_base(&self) -> &dyn Base;
+}
+
+impl Base for u32 {
+    fn as_t(&self) -> &dyn T {
+        self
+    }
+}
+impl Derived for u32 {
+    fn as_base(&self) -> &dyn Base {
+        self
+    }
+}
 
 impl<Q> T for Q where Q: Debug + Sync + AsMut<dyn T> {}
 
@@ -21,6 +38,16 @@ mock!{
     }
 }
 
+mock! {
+    Bar {}
+    impl Base for Bar {
+        fn as_t(&self) -> &dyn T;
+    }
+    impl Derived for Bar {
+        fn as_base(&self) -> &dyn Base;
+    }
+}
+
 #[test]
 fn return_const() {
     let mut mock = MockFoo::new();
@@ -47,3 +74,12 @@ fn return_var() {
 
     mock.baz().mutate();
 }
+
+#[test]
+fn dyn_upcast() {
+    let mut mock = MockBar::new();
+    mock.expect_as_t()
+        .return_const(Box::new(42u32) as Box<dyn T>);
+
+    assert_eq!("42", format!("{:?}", mock.as_t()));
+}
diff --git a/mockall_derive/src/mock_function.rs b/mockall_derive/src/mock_function.rs
index b560c60a..e704d9ba 100644
--- a/mockall_derive/src/mock_function.rs
+++ b/mockall_derive/src/mock_function.rs
@@ -4,7 +4,7 @@ use super::*;
 use quote::ToTokens;
 
 /// Convert a trait object reference into a reference to a Boxed trait
-fn dedynify(ty: &mut Type) {
+fn dedynify(ty: &mut Type) -> bool {
     if let Type::Reference(ref mut tr) = ty {
         if let Type::TraitObject(ref tto) = tr.elem.as_ref() {
             if let Some(lt) = &tr.lifetime {
@@ -17,13 +17,15 @@ fn dedynify(ty: &mut Type) {
                     // when methods like returning add a `+ Send` to the output
                     // type.
                     *tr.elem = parse2(quote!((#tto))).unwrap();
-                    return;
+                    return false;
                 }
             }
 
             *tr.elem = parse2(quote!(Box<#tto>)).unwrap();
+            return true;
         }
     }
+    false
 }
 
 /// Convert a special reference type like "&str" into a reference to its owned
@@ -207,16 +209,19 @@ impl<'a> Builder<'a> {
                 is_static = false;
             }
         }
-        let output = match self.sig.output {
-            ReturnType::Default => Type::Tuple(TypeTuple {
+        let (output, boxed) = match self.sig.output {
+            ReturnType::Default => (
+                Type::Tuple(TypeTuple {
                     paren_token: token::Paren::default(),
-                    elems: Punctuated::new()
+                    elems: Punctuated::new(),
                 }),
+                false,
+            ),
             ReturnType::Type(_, ref ty) => {
                 let mut output_ty = supersuperfy(&**ty, self.levels);
                 destrify(&mut output_ty);
-                dedynify(&mut output_ty);
-                output_ty
+                let boxed = dedynify(&mut output_ty);
+                (output_ty, boxed)
             }
         };
         supersuperfy_generics(&mut declosured_generics, self.levels);
@@ -284,6 +289,7 @@ impl<'a> Builder<'a> {
             mod_ident: self.parent.unwrap_or(&Ident::new("FIXME", Span::call_site())).clone(),
             output,
             owned_output,
+            boxed,
             predexprs,
             predty,
             refpredty,
@@ -389,6 +395,8 @@ pub(crate) struct MockFunction {
     /// If the real output type is a non-'static reference, then it will differ
     /// from this field.
     owned_output: Type,
+    /// True if the `owned_type` is boxed by `Box<>`.
+    boxed: bool,
     /// Expressions that create the predicate arguments from the call arguments
     predexprs: Vec<TokenStream>,
     /// Types used for Predicates.  Will be almost the same as args, but every
@@ -452,6 +460,14 @@ impl MockFunction {
         } else {
             Ident::new("call", Span::call_site())
         };
+        let mut deref = quote!();
+        if self.boxed {
+            if self.return_ref {
+                deref = quote! ( & * * );
+            } else if self.return_refmut {
+                deref = quote ! ( & mut * * );
+            }
+        }
         if self.is_static {
             let outer_mod_path = self.outer_mod_path(modname);
             quote!(
@@ -459,7 +475,7 @@ impl MockFunction {
                 #(#attrs)*
                 #vis #sig {
                     let no_match_msg = #no_match_msg;
-                    {
+                    #deref {
                         let __mockall_guard = #outer_mod_path::EXPECTATIONS
                             .lock().unwrap();
                         /*
@@ -479,7 +495,7 @@ impl MockFunction {
                 #(#attrs)*
                 #vis #sig {
                     let no_match_msg = #no_match_msg;
-                    self.#substruct_obj #name.#call#tbf(#(#call_exprs,)*)
+                    #deref self.#substruct_obj #name.#call#tbf(#(#call_exprs,)*)
                     .expect(&no_match_msg)
                 }