diff --git a/include/swift/AST/DiagnosticsSema.def b/include/swift/AST/DiagnosticsSema.def
index 21d77dc607818..6341287269f12 100644
--- a/include/swift/AST/DiagnosticsSema.def
+++ b/include/swift/AST/DiagnosticsSema.def
@@ -1419,6 +1419,15 @@ ERROR(optional_chain_isnt_chaining,none,
       ())
 ERROR(pattern_in_expr,none,
       "%0 cannot appear in an expression", (DescriptivePatternKind))
+ERROR(conditional_cast_in_type_casting_pattern,none,
+      "cannot conditionally downcast in a type-casting pattern",
+      ())
+ERROR(force_cast_in_type_casting_pattern,none,
+      "cannot force downcast in a type-casting pattern",
+      ())
+ERROR(cannot_bind_value_with_is,none,
+      "use 'as' keyword to bind a matched value",
+      ())
 NOTE(note_call_to_operator,none,
      "in call to operator %0", (const ValueDecl *))
 NOTE(note_call_to_func,none,
diff --git a/lib/Sema/CSDiagnostics.cpp b/lib/Sema/CSDiagnostics.cpp
index 6539f5f47832e..b1e3adedbb3d4 100644
--- a/lib/Sema/CSDiagnostics.cpp
+++ b/lib/Sema/CSDiagnostics.cpp
@@ -8699,10 +8699,47 @@ bool InvalidPatternInExprFailure::diagnoseAsError() {
       E = parent;
     }
   }
-  emitDiagnostic(diag::pattern_in_expr, P->getDescriptiveKind());
+  if (!diagnoseInvalidCheckedCast()) {
+    emitDiagnostic(diag::pattern_in_expr, P->getDescriptiveKind());
+  }
   return true;
 }
 
+bool InvalidPatternInExprFailure::diagnoseInvalidCheckedCast() const {
+  auto *E = findParentExpr(castToExpr(getAnchor()));
+  // Make sure we have a CheckedCastExpr and are in an argument of `~=`.
+  while (E && !isa<CheckedCastExpr>(E))
+    E = findParentExpr(E);
+  auto *castExpr = cast_or_null<CheckedCastExpr>(E);
+  if (!castExpr)
+    return false;
+  auto *parent = findParentExpr(castExpr);
+  while (parent && !isa<BinaryExpr>(parent))
+    parent = findParentExpr(parent);
+  auto *BE = cast_or_null<BinaryExpr>(parent);
+  if (!BE || !isPatternMatchingOperator(BE->getFn()))
+    return false;
+  // Emit the appropriate diagnostic based on the cast kind.
+  if (auto *forced = dyn_cast<ForcedCheckedCastExpr>(castExpr)) {
+    emitDiagnosticAt(castExpr->getLoc(),
+                     diag::force_cast_in_type_casting_pattern)
+        .fixItRemove(forced->getExclaimLoc());
+    return true;
+  }
+  if (auto *conditional = dyn_cast<ConditionalCheckedCastExpr>(castExpr)) {
+    emitDiagnosticAt(castExpr->getLoc(),
+                     diag::conditional_cast_in_type_casting_pattern)
+        .fixItRemove(conditional->getQuestionLoc());
+    return true;
+  }
+  if (auto *isExpr = dyn_cast<IsExpr>(castExpr)) {
+    emitDiagnosticAt(castExpr->getLoc(), diag::cannot_bind_value_with_is)
+        .fixItReplace(isExpr->getAsLoc(), "as");
+    return true;
+  }
+  return false;
+}
+
 bool MissingContextualTypeForNil::diagnoseAsError() {
   auto *expr = castToExpr<NilLiteralExpr>(getAnchor());
 
diff --git a/lib/Sema/CSDiagnostics.h b/lib/Sema/CSDiagnostics.h
index cd20db5e86cf9..df73e2ab64619 100644
--- a/lib/Sema/CSDiagnostics.h
+++ b/lib/Sema/CSDiagnostics.h
@@ -2604,6 +2604,18 @@ class InvalidPatternInExprFailure final : public FailureDiagnostic {
       : FailureDiagnostic(solution, locator), P(pattern) {}
 
   bool diagnoseAsError() override;
+
+private:
+  /// Diagnose situations where a type-casting pattern that binds a value
+  /// expects 'as' but is given 'as!', 'as?' or 'is' instead
+  /// e.g:
+  ///
+  /// \code
+  /// case let x as? Int = y
+  /// case let x as! Int = y
+  /// case let x is Int = y
+  /// \endcode
+  bool diagnoseInvalidCheckedCast() const;
 };
 
 /// Diagnose situations where there is no context to determine a
diff --git a/test/Constraints/rdar106598067.swift b/test/Constraints/rdar106598067.swift
index 1579dc002216a..e237f66a21033 100644
--- a/test/Constraints/rdar106598067.swift
+++ b/test/Constraints/rdar106598067.swift
@@ -3,10 +3,22 @@
 enum E: Error { case e }
 
 // rdar://106598067 – Make sure we don't crash.
-// FIXME: We ought to have a tailored diagnostic to change to 'as' instead of 'as?'
 let fn = {
   do {} catch let x as? E {}
-  // expected-error@-1 {{pattern variable binding cannot appear in an expression}}
+  // expected-error@-1 {{cannot conditionally downcast in a type-casting pattern}}{{23-24=}}
   // expected-error@-2 {{expression pattern of type 'E?' cannot match values of type 'any Error'}}
   // expected-warning@-3 {{'catch' block is unreachable because no errors are thrown in 'do' block}}
 }
+
+// https://github.com/swiftlang/swift/issues/44631
+let maybeInt: Any = 1
+switch maybeInt {
+case let intValue as? Int: _ = intValue
+  // expected-error@-1 {{cannot conditionally downcast in a type-casting pattern}}{{21-22=}}
+  // expected-error@-2 {{expression pattern of type 'Int?' cannot match values of type 'Any'}}
+case let intValue as! Int: _ = intValue
+  // expected-error@-1 {{cannot force downcast in a type-casting pattern}}{{21-22=}}
+case let intValue is Int: _ = intValue
+  // expected-error@-1 {{use 'as' keyword to bind a matched value}}{{19-21=as}}
+default: break
+}