diff --git a/lib/Sema/CSOptimizer.cpp b/lib/Sema/CSOptimizer.cpp
index df67f91bfdd3d..7cb263d55d839 100644
--- a/lib/Sema/CSOptimizer.cpp
+++ b/lib/Sema/CSOptimizer.cpp
@@ -17,6 +17,7 @@
 #include "OpenedExistentials.h"
 #include "TypeChecker.h"
 #include "swift/AST/ConformanceLookup.h"
+#include "swift/AST/Decl.h"
 #include "swift/AST/ExistentialLayout.h"
 #include "swift/AST/Expr.h"
 #include "swift/AST/GenericSignature.h"
@@ -768,7 +769,7 @@ static std::optional<DisjunctionInfo> preserveFavoringOfUnlabeledUnaryArgument(
   SmallVector<Constraint *, 2> favoredChoices;
   forEachDisjunctionChoice(
       cs, disjunction,
-      [&argumentType, &favoredChoices, &argument](
+      [&cs, &argumentType, &favoredChoices, &argument](
           Constraint *choice, ValueDecl *decl, FunctionType *overloadType) {
         if (decl->getAttrs().hasAttribute<DisfavoredOverloadAttr>())
           return;
@@ -784,8 +785,15 @@ static std::optional<DisjunctionInfo> preserveFavoringOfUnlabeledUnaryArgument(
             (isa<LiteralExpr>(argument) || isa<BinaryExpr>(argument)))
           return;
 
-        if (argumentType->isEqual(param.getPlainType()))
+        if (argumentType->isEqual(param.getPlainType())) {
+          if (auto *func = dyn_cast<AbstractFunctionDecl>(decl)) {
+            if (func->isAsyncContext() !=
+                cs.isAsynchronousContext(choice->getDeclContext()))
+              return;
+          }
+
           favoredChoices.push_back(choice);
+        }
       });
 
   return DisjunctionInfoBuilder(/*score=*/favoredChoices.empty() ? 0 : 1,
diff --git a/test/Constraints/old_hack_related_ambiguities.swift b/test/Constraints/old_hack_related_ambiguities.swift
index ff5248595cf09..d69ec110ac88b 100644
--- a/test/Constraints/old_hack_related_ambiguities.swift
+++ b/test/Constraints/old_hack_related_ambiguities.swift
@@ -383,3 +383,34 @@ do {
     }
   }
 }
+
+// Calls with single unlabeled arguments shouldn't favor overloads that don't match on async.
+do {
+  struct V {
+    var data: Int = 0
+  }
+
+  func test(_: Int) -> Int { 42 }
+  func test(_: Int, v: Int = 42) async -> V? { nil }
+
+  func doAsync<T>(_ fn: () async -> T) async -> T { await fn() }
+
+  func computeAsync(v: Int) async {
+    let v1 = await test(v)
+    if let v1 {
+      _ = v1.data // Ok
+    }
+
+    let v2 = await doAsync { await test(v) }
+    if let v2 {
+      _ = v2.data // Ok
+    }
+
+    _ = await doAsync {
+      let v = await test(v)
+      if let v {
+        _ = v.data // Ok
+      }
+    }
+  }
+}