diff --git a/lib/Sema/CSDiagnostics.cpp b/lib/Sema/CSDiagnostics.cpp
index 3f5760975f2f1..295e54891cd9b 100644
--- a/lib/Sema/CSDiagnostics.cpp
+++ b/lib/Sema/CSDiagnostics.cpp
@@ -5973,6 +5973,9 @@ bool ArgumentMismatchFailure::diagnoseAsError() {
   if (diagnoseTrailingClosureMismatch())
     return true;
 
+  if (diagnoseKeyPathAsFunctionResultMismatch())
+    return true;
+
   auto argType = getFromType();
   auto paramType = getToType();
 
@@ -6227,6 +6230,31 @@ bool ArgumentMismatchFailure::diagnoseTrailingClosureMismatch() const {
   return true;
 }
 
+bool ArgumentMismatchFailure::diagnoseKeyPathAsFunctionResultMismatch() const {
+  auto argExpr = getArgExpr();
+  if (!isExpr<KeyPathExpr>(argExpr))
+    return false;
+
+  auto argType = getFromType();
+  auto paramType = getToType();
+
+  if (!isKnownKeyPathType(argType))
+    return false;
+
+  auto kpType = argType->castTo<BoundGenericType>();
+  auto kpRootType = kpType->getGenericArgs()[0];
+  auto kpValueType = kpType->getGenericArgs()[1];
+
+  auto paramFnType = paramType->getAs<FunctionType>();
+  if (!(paramFnType && paramFnType->getNumParams() == 1 &&
+        paramFnType->getParams().front().getPlainType()->isEqual(kpRootType)))
+    return false;
+
+  emitDiagnostic(diag::expr_smart_keypath_value_covert_to_contextual_type,
+                 kpValueType, paramFnType->getResult());
+  return true;
+}
+
 void ExpandArrayIntoVarargsFailure::tryDropArrayBracketsFixIt(
     const Expr *anchor) const {
   // If this is an array literal, offer to remove the brackets and pass the
diff --git a/lib/Sema/CSDiagnostics.h b/lib/Sema/CSDiagnostics.h
index 329998d592d29..97285c499c9d0 100644
--- a/lib/Sema/CSDiagnostics.h
+++ b/lib/Sema/CSDiagnostics.h
@@ -1909,6 +1909,12 @@ class ArgumentMismatchFailure : public ContextualFailure {
   /// closures being passed to non-closure parameters.
   bool diagnoseTrailingClosureMismatch() const;
 
+  /// Tailored key path as function diagnostics for argument mismatches where
+  /// argument is a keypath expression that has a root type that matches a
+  /// function parameter, but keypath value don't match the function parameter
+  /// result value.
+  bool diagnoseKeyPathAsFunctionResultMismatch() const;
+
 protected:
   /// \returns The position of the argument being diagnosed, starting at 1.
   unsigned getArgPosition() const { return Info.getArgPosition(); }
diff --git a/lib/Sema/CSSimplify.cpp b/lib/Sema/CSSimplify.cpp
index 38f71d0fb481b..654be8eac9684 100644
--- a/lib/Sema/CSSimplify.cpp
+++ b/lib/Sema/CSSimplify.cpp
@@ -3795,10 +3795,13 @@ bool ConstraintSystem::repairFailures(
     // there is going to be a constraint to match result of the
     // member lookup to the generic parameter `V` of *KeyPath<R, V>
     // type associated with key path expression, which we need to
-    // fix-up here.
-    if (isExpr<KeyPathExpr>(anchor)) {
-      auto *fnType = lhs->getAs<FunctionType>();
-      if (fnType && fnType->getResult()->isEqual(rhs))
+    // fix-up here unless last component has already a invalid type or
+    // instance fix recorded.
+    if (auto *kpExpr = getAsExpr<KeyPathExpr>(anchor)) {
+      auto i = kpExpr->getComponents().size() - 1;
+      auto lastCompLoc = getConstraintLocator(
+          locator.withPathElement(LocatorPathElt::KeyPathComponent(i)));
+      if (hasFixFor(lastCompLoc, FixKind::AllowTypeOrInstanceMember))
         return true;
 
       auto lastComponentType = lhs->lookThroughAllOptionalTypes();
diff --git a/test/expr/unary/keypath/keypath.swift b/test/expr/unary/keypath/keypath.swift
index 50bdded7d12bc..923bcd05f5abe 100644
--- a/test/expr/unary/keypath/keypath.swift
+++ b/test/expr/unary/keypath/keypath.swift
@@ -795,6 +795,7 @@ func test_keypath_with_method_refs() {
   }
 
   let _: KeyPath<S, Int> = \.foo // expected-error {{key path cannot refer to instance method 'foo()'}}
+  // expected-error@-1 {{key path value type '() -> Int' cannot be converted to contextual type 'Int'}}
   let _: KeyPath<S, Int> = \.bar // expected-error {{key path cannot refer to static member 'bar()'}}
   let _ = \S.Type.bar // expected-error {{key path cannot refer to static method 'bar()'}}
 
@@ -1094,3 +1095,19 @@ func rdar74711236() {
     }()
   }
 }
+
+extension String {
+  var filterOut : (Self) throws -> Bool {
+    { $0.contains("a") }
+  }
+}
+
+func test_kp_as_function_mismatch() {
+  let a : [String] = [ "asd", "bcd", "def" ]
+
+  let _ : (String) ->  Bool = \.filterOut // expected-error{{key path value type '(String) throws -> Bool' cannot be converted to contextual type 'Bool'}}
+  _ = a.filter(\.filterOut) // expected-error{{key path value type '(String) throws -> Bool' cannot be converted to contextual type 'Bool'}}
+  let _ : (String) ->  Bool = \String.filterOut // expected-error{{key path value type '(String) throws -> Bool' cannot be converted to contextual type 'Bool'}}
+  _ = a.filter(\String.filterOut) // expected-error{{key path value type '(String) throws -> Bool' cannot be converted to contextual type 'Bool'}}
+
+}