diff --git a/src/compiler/checker.ts b/src/compiler/checker.ts
index a8a14dc9b66a5..b155f3dfab106 100644
--- a/src/compiler/checker.ts
+++ b/src/compiler/checker.ts
@@ -34547,9 +34547,7 @@ namespace ts {
                 : isBinaryExpression(location) && isIdentifier(location.right) ? location.right
                 : undefined;
             const isPropertyExpressionCast = isPropertyAccessExpression(location)
-                && isParenthesizedExpression(location.expression)
-                && isAssertionExpression(location.expression.expression);
-
+                && isAssertionExpression(skipParentheses(location.expression));
             if (!testedNode || isPropertyExpressionCast) {
                 return;
             }
diff --git a/tests/baselines/reference/truthinessCallExpressionCoercion3.js b/tests/baselines/reference/truthinessCallExpressionCoercion3.js
index a2ab27f21a2ef..7fc1df8ffb574 100644
--- a/tests/baselines/reference/truthinessCallExpressionCoercion3.js
+++ b/tests/baselines/reference/truthinessCallExpressionCoercion3.js
@@ -9,6 +9,11 @@ function f(result: unknown) {
         return result
     }
 }
+function g(result: unknown) {
+    if (((result as I)).always) {
+        return result
+    }
+}
 
 
 //// [truthinessCallExpressionCoercion3.js]
@@ -17,3 +22,8 @@ function f(result) {
         return result;
     }
 }
+function g(result) {
+    if (result.always) {
+        return result;
+    }
+}
diff --git a/tests/baselines/reference/truthinessCallExpressionCoercion3.symbols b/tests/baselines/reference/truthinessCallExpressionCoercion3.symbols
index 35392c06aef0e..e7ed13514df6c 100644
--- a/tests/baselines/reference/truthinessCallExpressionCoercion3.symbols
+++ b/tests/baselines/reference/truthinessCallExpressionCoercion3.symbols
@@ -21,4 +21,18 @@ function f(result: unknown) {
 >result : Symbol(result, Decl(truthinessCallExpressionCoercion3.ts, 5, 11))
     }
 }
+function g(result: unknown) {
+>g : Symbol(g, Decl(truthinessCallExpressionCoercion3.ts, 9, 1))
+>result : Symbol(result, Decl(truthinessCallExpressionCoercion3.ts, 10, 11))
+
+    if (((result as I)).always) {
+>((result as I)).always : Symbol(I.always, Decl(truthinessCallExpressionCoercion3.ts, 1, 13))
+>result : Symbol(result, Decl(truthinessCallExpressionCoercion3.ts, 10, 11))
+>I : Symbol(I, Decl(truthinessCallExpressionCoercion3.ts, 0, 0))
+>always : Symbol(I.always, Decl(truthinessCallExpressionCoercion3.ts, 1, 13))
+
+        return result
+>result : Symbol(result, Decl(truthinessCallExpressionCoercion3.ts, 10, 11))
+    }
+}
 
diff --git a/tests/baselines/reference/truthinessCallExpressionCoercion3.types b/tests/baselines/reference/truthinessCallExpressionCoercion3.types
index 200ddbfa13ecc..3d10a48a7f68e 100644
--- a/tests/baselines/reference/truthinessCallExpressionCoercion3.types
+++ b/tests/baselines/reference/truthinessCallExpressionCoercion3.types
@@ -20,4 +20,20 @@ function f(result: unknown) {
 >result : unknown
     }
 }
+function g(result: unknown) {
+>g : (result: unknown) => unknown
+>result : unknown
+
+    if (((result as I)).always) {
+>((result as I)).always : () => void
+>((result as I)) : I
+>(result as I) : I
+>result as I : I
+>result : unknown
+>always : () => void
+
+        return result
+>result : unknown
+    }
+}
 
diff --git a/tests/cases/compiler/truthinessCallExpressionCoercion3.ts b/tests/cases/compiler/truthinessCallExpressionCoercion3.ts
index 69f6ba8214d40..948e8059cf14a 100644
--- a/tests/cases/compiler/truthinessCallExpressionCoercion3.ts
+++ b/tests/cases/compiler/truthinessCallExpressionCoercion3.ts
@@ -11,3 +11,8 @@ function f(result: unknown) {
         return result
     }
 }
+function g(result: unknown) {
+    if (((result as I)).always) {
+        return result
+    }
+}