diff --git a/compiler/rustc_span/src/symbol.rs b/compiler/rustc_span/src/symbol.rs
index 7b0138d50baed..6c4eb5d570519 100644
--- a/compiler/rustc_span/src/symbol.rs
+++ b/compiler/rustc_span/src/symbol.rs
@@ -1154,6 +1154,7 @@ symbols! {
         offset_of,
         offset_of_enum,
         offset_of_nested,
+        ok_or,
         ok_or_else,
         omit_gdb_pretty_printer_section,
         on,
diff --git a/compiler/rustc_trait_selection/src/traits/error_reporting/type_err_ctxt_ext.rs b/compiler/rustc_trait_selection/src/traits/error_reporting/type_err_ctxt_ext.rs
index 149dcffe333de..7d371a4226193 100644
--- a/compiler/rustc_trait_selection/src/traits/error_reporting/type_err_ctxt_ext.rs
+++ b/compiler/rustc_trait_selection/src/traits/error_reporting/type_err_ctxt_ext.rs
@@ -1155,6 +1155,19 @@ impl<'tcx> TypeErrCtxtExt<'tcx> for TypeErrCtxt<'_, 'tcx> {
                 );
             }
 
+            if path_segment.ident.name == sym::ok_or && is_diagnostic_item(sym::Option, next_ty) {
+                err.span_suggestion(
+                    path_segment.ident.span,
+                    format!(
+                        "`?` expected `{}` for `Err` variant but found `{:?}`. Use the `ok_or_else` method to pass a closure",
+                        self_ty,
+                        get_e_type(prev_ty).unwrap().to_string(),
+                    ),
+                    "ok_or_else",
+                    Applicability::MachineApplicable,
+                );
+            }
+
             prev_ty = next_ty;
 
             if let hir::ExprKind::Path(hir::QPath::Resolved(None, path)) = expr.kind
diff --git a/tests/ui/closures/closure-ok-or.fixed b/tests/ui/closures/closure-ok-or.fixed
new file mode 100644
index 0000000000000..2ebe4fcab003f
--- /dev/null
+++ b/tests/ui/closures/closure-ok-or.fixed
@@ -0,0 +1,8 @@
+// run-rustfix
+
+// issue #119765
+
+fn main() -> Result<(), bool> {
+    None.ok_or_else(|| true)?
+    //~^ ERROR `?` couldn't convert the error to `bool` [E0277]
+}
diff --git a/tests/ui/closures/closure-ok-or.rs b/tests/ui/closures/closure-ok-or.rs
new file mode 100644
index 0000000000000..6b0c8abfe0498
--- /dev/null
+++ b/tests/ui/closures/closure-ok-or.rs
@@ -0,0 +1,8 @@
+// run-rustfix
+
+// issue #119765
+
+fn main() -> Result<(), bool> {
+    None.ok_or(|| true)?
+    //~^ ERROR `?` couldn't convert the error to `bool` [E0277]
+}
diff --git a/tests/ui/closures/closure-ok-or.stderr b/tests/ui/closures/closure-ok-or.stderr
new file mode 100644
index 0000000000000..2584d2c489f9c
--- /dev/null
+++ b/tests/ui/closures/closure-ok-or.stderr
@@ -0,0 +1,23 @@
+error[E0277]: `?` couldn't convert the error to `bool`
+  --> $DIR/closure-ok-or.rs:6:24
+   |
+LL | fn main() -> Result<(), bool> {
+   |              ---------------- expected `bool` because of this
+LL |     None.ok_or(|| true)?
+   |          --------------^ the trait `From<{closure@$DIR/closure-ok-or.rs:6:16: 6:18}>` is not implemented for `bool`
+   |          |
+   |          this can't be annotated with `?` because it has type `Result<_, {closure@$DIR/closure-ok-or.rs:6:16: 6:18}>`
+   |
+   = note: the question mark operation (`?`) implicitly performs a conversion on the error value using the `From` trait
+   = help: the following other types implement trait `FromResidual<R>`:
+             <Result<T, F> as FromResidual<Yeet<E>>>
+             <Result<T, F> as FromResidual<Result<Infallible, E>>>
+   = note: required for `Result<(), bool>` to implement `FromResidual<Result<Infallible, {closure@$DIR/closure-ok-or.rs:6:16: 6:18}>>`
+help: `?` expected `bool` for `Err` variant but found `"{closure@$DIR/closure-ok-or.rs:6:16: 6:18}"`. Use the `ok_or_else` method to pass a closure
+   |
+LL |     None.ok_or_else(|| true)?
+   |          ~~~~~~~~~~
+
+error: aborting due to 1 previous error
+
+For more information about this error, try `rustc --explain E0277`.