diff --git a/src/jsc/bindings/bindings.cpp b/src/jsc/bindings/bindings.cpp
index 57d17e089678..48e9cad873ec 100644
--- a/src/jsc/bindings/bindings.cpp
+++ b/src/jsc/bindings/bindings.cpp
@@ -2337,13 +2337,19 @@ extern "C" JSC::EncodedJSValue JSC__JSValue__unwrapBoxedPrimitive(JSGlobalObject
         return JSValue::encode(value);
     }
 
+    auto scope = DECLARE_THROW_SCOPE(globalObject->vm());
     JSObject* object = asObject(value);
 
     if (object->inherits<NumberObject>()) {
-        return JSValue::encode(jsNumber(object->toNumber(globalObject)));
+        double number = object->toNumber(globalObject);
+        RETURN_IF_EXCEPTION(scope, {});
+        return JSValue::encode(jsNumber(number));
+    }
+    if (object->inherits<StringObject>()) {
+        JSString* string = object->toString(globalObject);
+        RETURN_IF_EXCEPTION(scope, {});
+        return JSValue::encode(string);
     }
-    if (object->inherits<StringObject>())
-        return JSValue::encode(object->toString(globalObject));
     if (object->inherits<BooleanObject>() || object->inherits<BigIntObject>())
         return JSValue::encode(uncheckedDowncast<JSWrapperObject>(object)->internalValue());
 
diff --git a/test/js/bun/yaml/yaml.test.ts b/test/js/bun/yaml/yaml.test.ts
index 4e99f3643fc6..a000041bb60c 100644
--- a/test/js/bun/yaml/yaml.test.ts
+++ b/test/js/bun/yaml/yaml.test.ts
@@ -3484,6 +3484,22 @@ config:
         expect(YAML.stringify(obj, null, 2)).toBe("num: \n  3.14\nstr: world\nbool: \n  false");
       });
 
+      test("propagates exceptions thrown while unwrapping boxed primitives", () => {
+        const boxedString = new String("x");
+        boxedString.toString = () => {
+          throw new Error("boom string");
+        };
+        expect(() => YAML.stringify(boxedString)).toThrow("boom string");
+        expect(() => YAML.stringify({ a: boxedString })).toThrow("boom string");
+
+        const boxedNumber = new Number(5);
+        boxedNumber.valueOf = () => {
+          throw new Error("boom number");
+        };
+        expect(() => YAML.stringify(boxedNumber)).toThrow("boom number");
+        expect(() => YAML.stringify([boxedNumber])).toThrow("boom number");
+      });
+
       test("handles Date objects", () => {
         // Date objects get converted to ISO string via toString()
         const date = new Date("2024-01-15T10:30:00Z");