diff --git a/slack_bolt/middleware/ssl_check/async_ssl_check.py b/slack_bolt/middleware/ssl_check/async_ssl_check.py
index 5b806a4bc..62712aa67 100644
--- a/slack_bolt/middleware/ssl_check/async_ssl_check.py
+++ b/slack_bolt/middleware/ssl_check/async_ssl_check.py
@@ -18,7 +18,7 @@ async def async_process(
         next: Callable[[], Awaitable[BoltResponse]],
     ) -> BoltResponse:
         if self._is_ssl_check_request(req.body):
-            if self._verify_token_if_needed(req.body):
+            if not self._verify_token_if_needed(req.body):
                 return self._build_error_response()
             return self._build_success_response()
         else:
diff --git a/slack_bolt/middleware/ssl_check/ssl_check.py b/slack_bolt/middleware/ssl_check/ssl_check.py
index 5e5d9ad9c..d7f6a759d 100644
--- a/slack_bolt/middleware/ssl_check/ssl_check.py
+++ b/slack_bolt/middleware/ssl_check/ssl_check.py
@@ -39,7 +39,7 @@ def process(
         next: Callable[[], BoltResponse],
     ) -> BoltResponse:
         if self._is_ssl_check_request(req.body):
-            if self._verify_token_if_needed(req.body):
+            if not self._verify_token_if_needed(req.body):
                 return self._build_error_response()
             return self._build_success_response()
         else:
@@ -51,8 +51,12 @@ def process(
     def _is_ssl_check_request(body: dict):
         return "ssl_check" in body and body["ssl_check"] == "1"
 
-    def _verify_token_if_needed(self, body: dict):
-        return self.verification_token and self.verification_token == body["token"]
+    def _verify_token_if_needed(self, body: dict) -> bool:
+        # Returns True when the request is acceptable: either no token check is configured,
+        # or the token in the body matches the configured one
+        if self.verification_token is None:
+            return True
+        return self.verification_token == body.get("token")
 
     @staticmethod
     def _build_success_response() -> BoltResponse:
diff --git a/tests/scenario_tests/test_ssl_check.py b/tests/scenario_tests/test_ssl_check.py
index 937f9d7e4..6cd146598 100644
--- a/tests/scenario_tests/test_ssl_check.py
+++ b/tests/scenario_tests/test_ssl_check.py
@@ -56,6 +56,32 @@ def test_ssl_check(self):
         assert response.status == 200
         assert response.body == ""
 
+    def test_ssl_check_with_verification_token(self):
+        app = App(client=self.web_client, signing_secret=self.signing_secret, verification_token="expected")
+
+        def dispatch(body: str):
+            timestamp = str(int(time()))
+            request = BoltRequest(
+                body=body,
+                query={},
+                headers={
+                    "content-type": ["application/x-www-form-urlencoded"],
+                    "x-slack-signature": [self.generate_signature(body, timestamp)],
+                    "x-slack-request-timestamp": [timestamp],
+                },
+            )
+            return app.dispatch(request)
+
+        response = dispatch("token=expected&ssl_check=1")
+        assert response.status == 200
+        assert response.body == ""
+
+        response = dispatch("token=wrong&ssl_check=1")
+        assert response.status == 401
+
+        response = dispatch("ssl_check=1")
+        assert response.status == 401
+
     def test_ssl_check_disabled(self):
         app = App(
             client=self.web_client,
diff --git a/tests/scenario_tests_async/test_ssl_check.py b/tests/scenario_tests_async/test_ssl_check.py
index ef32bc0dd..f1967163b 100644
--- a/tests/scenario_tests_async/test_ssl_check.py
+++ b/tests/scenario_tests_async/test_ssl_check.py
@@ -61,3 +61,30 @@ async def test_ssl_check(self):
         response = await app.async_dispatch(request)
         assert response.status == 200
         assert response.body == ""
+
+    @pytest.mark.asyncio
+    async def test_ssl_check_with_verification_token(self):
+        app = AsyncApp(client=self.web_client, signing_secret=self.signing_secret, verification_token="expected")
+
+        async def dispatch(body: str):
+            timestamp = str(int(time()))
+            request = AsyncBoltRequest(
+                body=body,
+                query={},
+                headers={
+                    "content-type": ["application/x-www-form-urlencoded"],
+                    "x-slack-signature": [self.generate_signature(body, timestamp)],
+                    "x-slack-request-timestamp": [timestamp],
+                },
+            )
+            return await app.async_dispatch(request)
+
+        response = await dispatch("token=expected&ssl_check=1")
+        assert response.status == 200
+        assert response.body == ""
+
+        response = await dispatch("token=wrong&ssl_check=1")
+        assert response.status == 401
+
+        response = await dispatch("ssl_check=1")
+        assert response.status == 401