diff --git a/compiler/rustc_typeck/src/check/expr.rs b/compiler/rustc_typeck/src/check/expr.rs
index 0e1dbc53806ff..536dec8442d84 100644
--- a/compiler/rustc_typeck/src/check/expr.rs
+++ b/compiler/rustc_typeck/src/check/expr.rs
@@ -831,9 +831,9 @@ impl<'a, 'tcx> FnCtxt<'a, 'tcx> {
         lhs: &'tcx hir::Expr<'tcx>,
         err_code: &'static str,
         op_span: Span,
-    ) {
+    ) -> Result<(), DiagnosticBuilder<'tcx>> {
         if lhs.is_syntactic_place_expr() {
-            return;
+            return Ok(());
         }
 
         // FIXME: Make this use SessionDiagnostic once error codes can be dynamically set.
@@ -885,7 +885,7 @@ impl<'a, 'tcx> FnCtxt<'a, 'tcx> {
             }
         }
 
-        err.emit();
+        Err(err)
     }
 
     // A generic function for checking the 'then' and 'else' clauses in an 'if'
@@ -1025,14 +1025,69 @@ impl<'a, 'tcx> FnCtxt<'a, 'tcx> {
             return self.tcx.ty_error();
         }
 
-        self.check_lhs_assignable(lhs, "E0070", *span);
+        let mut assignable_err = self.check_lhs_assignable(lhs, "E0070", *span);
 
         let lhs_ty = self.check_expr_with_needs(&lhs, Needs::MutPlace);
-        let rhs_ty = self.check_expr_coercable_to_type(&rhs, lhs_ty, Some(lhs));
+        let rhs_ty = self.check_expr_with_hint(&rhs, lhs_ty);
+
+        let (mut coerce_ty, mut coerce_err) =
+            self.demand_coerce_diag(&rhs, rhs_ty, lhs_ty, Some(&lhs), AllowTwoPhase::No);
+
+        // If we either have a bad LHS type, or can't coerce the RHS into the LHS, it may be due
+        // to a missing deref on the LHS.
+        if assignable_err.is_err() || coerce_err.is_some() {
+            for (deref_ty, steps) in self.autoderef(lhs.span, lhs_ty) {
+                // Check if we can deref the LHS into something that the RHS can coerce into
+                if self.can_coerce(rhs_ty, deref_ty) {
+                    coerce_ty = lhs_ty;
+                    let span = lhs.span.shrink_to_lo();
+                    let msg = "consider dereferencing here to assign a value to the left-hand side";
+                    let suggest = "*".repeat(steps);
+                    // We don't need to emit both an LHS error and a coercion error,
+                    // so prefer emitting the LHS error over the coercion error
+                    match (&mut assignable_err, &mut coerce_err) {
+                        (Err(err), Some(coerce_err)) => {
+                            // Cancel the coercion error if we have both
+                            coerce_err.cancel();
+                            err.span_suggestion_verbose(
+                                span,
+                                msg,
+                                suggest,
+                                Applicability::MaybeIncorrect,
+                            );
+                            err.emit();
+                        }
+                        (Err(err), None) | (Ok(()), Some(err)) => {
+                            err.span_suggestion_verbose(
+                                span,
+                                msg,
+                                suggest,
+                                Applicability::MaybeIncorrect,
+                            );
+                            err.emit();
+                        }
+                        (Ok(()), None) => unreachable!(),
+                    }
+                    break;
+                }
+            }
+        }
+
+        // Emit any leftover errors if we still have them after checking for deref
+        if let Some(mut err) = coerce_err {
+            if !err.cancelled() {
+                err.emit();
+            }
+        }
+        if let Err(mut err) = assignable_err {
+            if !err.cancelled() {
+                err.emit();
+            }
+        }
 
         self.require_type_is_sized(lhs_ty, lhs.span, traits::AssignmentLhsSized);
 
-        if lhs_ty.references_error() || rhs_ty.references_error() {
+        if lhs_ty.references_error() || coerce_ty.references_error() {
             self.tcx.ty_error()
         } else {
             self.tcx.mk_unit()
diff --git a/compiler/rustc_typeck/src/check/op.rs b/compiler/rustc_typeck/src/check/op.rs
index 74516acbfcff3..f8e8eb46b1913 100644
--- a/compiler/rustc_typeck/src/check/op.rs
+++ b/compiler/rustc_typeck/src/check/op.rs
@@ -42,7 +42,9 @@ impl<'a, 'tcx> FnCtxt<'a, 'tcx> {
                 return_ty
             };
 
-        self.check_lhs_assignable(lhs, "E0067", op.span);
+        if let Err(mut err) = self.check_lhs_assignable(lhs, "E0067", op.span) {
+            err.emit();
+        }
 
         ty
     }
diff --git a/src/test/ui/typeck/bad-lhs-should-deref.rs b/src/test/ui/typeck/bad-lhs-should-deref.rs
new file mode 100644
index 0000000000000..c62f654e73267
--- /dev/null
+++ b/src/test/ui/typeck/bad-lhs-should-deref.rs
@@ -0,0 +1,15 @@
+fn mut_ref() -> &'static mut Box<usize> {
+    todo!();
+}
+
+fn main() {
+    mut_ref() = 1;
+    //~^ ERROR invalid left-hand side of assignment
+    //~| HELP consider dereferencing here to assign a value to the left-hand side
+
+    let x = Box::new(1);
+    x = 2;
+    //~^ ERROR mismatched types
+    //~| HELP store this in the heap by calling `Box::new`
+    //~| HELP consider dereferencing here to assign a value to the left-hand side
+}
diff --git a/src/test/ui/typeck/bad-lhs-should-deref.stderr b/src/test/ui/typeck/bad-lhs-should-deref.stderr
new file mode 100644
index 0000000000000..caedc23019239
--- /dev/null
+++ b/src/test/ui/typeck/bad-lhs-should-deref.stderr
@@ -0,0 +1,37 @@
+error[E0070]: invalid left-hand side of assignment
+  --> $DIR/bad-lhs-should-deref.rs:6:15
+   |
+LL |     mut_ref() = 1;
+   |     --------- ^
+   |     |
+   |     cannot assign to this expression
+   |
+help: consider dereferencing here to assign a value to the left-hand side
+   |
+LL |     **mut_ref() = 1;
+   |     ++
+
+error[E0308]: mismatched types
+  --> $DIR/bad-lhs-should-deref.rs:11:9
+   |
+LL |     let x = Box::new(1);
+   |             ----------- expected due to this value
+LL |     x = 2;
+   |         ^ expected struct `Box`, found integer
+   |
+   = note: expected struct `Box<{integer}>`
+                found type `{integer}`
+   = note: for more on the distinction between the stack and the heap, read https://doc.rust-lang.org/book/ch15-01-box.html, https://doc.rust-lang.org/rust-by-example/std/box.html, and https://doc.rust-lang.org/std/boxed/index.html
+help: store this in the heap by calling `Box::new`
+   |
+LL |     x = Box::new(2);
+   |         +++++++++ +
+help: consider dereferencing here to assign a value to the left-hand side
+   |
+LL |     *x = 2;
+   |     +
+
+error: aborting due to 2 previous errors
+
+Some errors have detailed explanations: E0070, E0308.
+For more information about an error, try `rustc --explain E0070`.