diff --git a/README.md b/README.md
index a14cd523..ebe79837 100644
--- a/README.md
+++ b/README.md
@@ -78,6 +78,13 @@ uvx scc_mcp
 uvx secops_soar_mcp --integrations CSV,OKTA
 ```
 
+If SecOps SOAR fails during startup with a TLS certificate verification error
+on macOS, install the CA list bundled with `certifi` for your Python version:
+
+```bash
+/Applications/Python\ 3.12/Install\ Certificates.command
+```
+
 With environment variables:
 
 ```bash
diff --git a/server/secops-soar/secops_soar_mcp/bindings.py b/server/secops-soar/secops_soar_mcp/bindings.py
index 094c1f1a..865d23e9 100644
--- a/server/secops-soar/secops_soar_mcp/bindings.py
+++ b/server/secops-soar/secops_soar_mcp/bindings.py
@@ -13,7 +13,9 @@
 # limitations under the License.
 """Bindings for the SOAR client."""
 
+from collections import deque
 import os
+import ssl
 
 import dotenv
 from logger_utils import get_logger
@@ -29,12 +31,56 @@
 valid_scopes = set()
 
 
+def _is_certificate_verification_error(error: BaseException | None) -> bool:
+    if error is None:
+        return False
+    pending = deque([error])
+    seen: set[int] = set()
+    while pending:
+        current = pending.popleft()
+        if id(current) in seen:
+            continue
+        seen.add(id(current))
+        message = str(current).lower()
+        if isinstance(current, ssl.SSLCertVerificationError):
+            return True
+        if (
+            isinstance(current, ssl.SSLError)
+            and "certificate verify failed" in message
+        ):
+            return True
+        if "certificate verify failed" in message:
+            return True
+        for related in (current.__cause__, current.__context__):
+            if isinstance(related, BaseException):
+                pending.append(related)
+        for arg in getattr(current, "args", ()):
+            if isinstance(arg, BaseException):
+                pending.append(arg)
+    return False
+
+
+def _valid_scopes_error_message(error: BaseException | None) -> str:
+    if _is_certificate_verification_error(error):
+        return (
+            "Failed to fetch valid scopes from SOAR because TLS certificate "
+            "verification failed. If you are using the Python.org macOS "
+            "installer, run the Install Certificates.command for your Python "
+            "version, for example: "
+            "`/Applications/Python\\ 3.12/Install\\ Certificates.command`. "
+            "You can also point Python at certifi's CA bundle with "
+            "`SSL_CERT_FILE=$(python -m certifi)`."
+        )
+    return (
+        "Failed to fetch valid scopes from SOAR, please make sure you have "
+        "configured the right SOAR credentials. Shutting down..."
+    )
+
+
 async def _get_valid_scopes():
     valid_scopes_list = await http_client.get(consts.Endpoints.GET_SCOPES)
     if valid_scopes_list is None:
-        raise RuntimeError(
-            "Failed to fetch valid scopes from SOAR, please make sure you have configured the right SOAR credentials. Shutting down..."
-        )
+        raise RuntimeError(_valid_scopes_error_message(http_client.last_error))
     return set(valid_scopes_list)
 
 
diff --git a/server/secops-soar/secops_soar_mcp/bindings_test.py b/server/secops-soar/secops_soar_mcp/bindings_test.py
new file mode 100644
index 00000000..5bfe1c3b
--- /dev/null
+++ b/server/secops-soar/secops_soar_mcp/bindings_test.py
@@ -0,0 +1,35 @@
+# Copyright 2025 Google LLC
+#
+# Licensed under the Apache License, Version 2.0 (the "License");
+# you may not use this file except in compliance with the License.
+# You may obtain a copy of the License at
+#
+#      https://www.apache.org/licenses/LICENSE-2.0
+#
+# Unless required by applicable law or agreed to in writing, software
+# distributed under the License is distributed on an "AS IS" BASIS,
+# WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+# See the License for the specific language governing permissions and
+# limitations under the License.
+
+"""Tests for SecOps SOAR binding startup errors."""
+
+import ssl
+
+from secops_soar_mcp import bindings
+
+
+def test_valid_scopes_error_message_identifies_certifi_issue():
+    error = ssl.SSLCertVerificationError("certificate verify failed")
+
+    message = bindings._valid_scopes_error_message(error)
+
+    assert "TLS certificate verification failed" in message
+    assert "Install Certificates.command" in message
+    assert "certifi" in message
+
+
+def test_valid_scopes_error_message_preserves_credentials_hint():
+    message = bindings._valid_scopes_error_message(RuntimeError("401 unauthorized"))
+
+    assert "configured the right SOAR credentials" in message
diff --git a/server/secops-soar/secops_soar_mcp/http_client.py b/server/secops-soar/secops_soar_mcp/http_client.py
index 1c03768b..13636a3c 100644
--- a/server/secops-soar/secops_soar_mcp/http_client.py
+++ b/server/secops-soar/secops_soar_mcp/http_client.py
@@ -29,6 +29,7 @@ def __init__(self, base_url: str, app_key: str):
         self.base_url = base_url
         self.app_key = app_key
         self._session = None
+        self.last_error: Exception | None = None
 
     def _get_session(self) -> aiohttp.ClientSession:
         if self._session is None:
@@ -56,6 +57,7 @@ async def get(
             The response as a JSON object, or None if an error occurred.
         """
         headers = await self._get_headers()
+        self.last_error = None
         try:
             async with self._get_session().get(
                 self.base_url + endpoint, params=params, headers=headers
@@ -63,8 +65,10 @@ async def get(
                 response.raise_for_status()  # Raise an exception for 4xx/5xx responses
                 return await response.json()
         except aiohttp.ClientResponseError as e:
+            self.last_error = e
             logger.debug("HTTP error occurred: %s", e)
         except Exception as e:
+            self.last_error = e
             logger.debug("An error occurred: %s", e)
         return None
 
@@ -85,6 +89,7 @@ async def post(
             The response as a JSON object, or None if an error occurred.
         """
         headers = await self._get_headers()
+        self.last_error = None
         try:
             async with self._get_session().post(
                 self.base_url + endpoint, json=req, params=params, headers=headers
@@ -94,8 +99,10 @@ async def post(
                 decoded_data = data.decode("utf-8")
                 return json.loads(decoded_data)
         except aiohttp.ClientResponseError as e:
+            self.last_error = e
             logger.debug("HTTP error occurred: %s", e)
         except Exception as e:
+            self.last_error = e
             logger.debug("An error occurred: %s", e)
         return None
 
@@ -116,6 +123,7 @@ async def patch(
             The response as a JSON object, or None if an error occurred.
         """
         headers = await self._get_headers()
+        self.last_error = None
         try:
             async with self._get_session().patch(
                 self.base_url + endpoint, json=req, params=params, headers=headers
@@ -123,8 +131,10 @@ async def patch(
                 response.raise_for_status()
                 return await response.json()
         except aiohttp.ClientResponseError as e:
+            self.last_error = e
             logger.debug("HTTP error occurred: %s", e)
         except Exception as e:
+            self.last_error = e
             logger.debug("An error occurred: %s", e)
         return None