diff --git a/command_line_assistant/daemon/http/session.py b/command_line_assistant/daemon/http/session.py
index 4a306fe..09ae341 100644
--- a/command_line_assistant/daemon/http/session.py
+++ b/command_line_assistant/daemon/http/session.py
@@ -1,6 +1,7 @@
 """Handle the http sessions that the daemon issues to the backend."""
 
 import logging
+from ssl import SSLError
 
 import urllib3
 from requests.sessions import Session
@@ -8,6 +9,7 @@
 from command_line_assistant.config import Config
 from command_line_assistant.constants import VERSION
 from command_line_assistant.daemon.http.adapters import RetryAdapter, SSLAdapter
+from command_line_assistant.dbus.exceptions import RequestFailedError
 
 USER_AGENT = f"clad/{VERSION}"
 #: Define the custom user agent for clad
@@ -46,10 +48,20 @@ def get_session(config: Config) -> Session:
         session.verify = False
         return session
 
-    ssl_adapter = SSLAdapter(
-        cert_file=config.backend.auth.cert_file,  # type: ignore
-        key_file=config.backend.auth.key_file,  # type: ignore
-    )
+    try:
+        ssl_adapter = SSLAdapter(
+            cert_file=config.backend.auth.cert_file,  # type: ignore
+            key_file=config.backend.auth.key_file,  # type: ignore
+        )
+    except SSLError as e:
+        raise RequestFailedError(
+            "Failed to load certificate in cert chain. If needed, regenerate the certificate with subscription-manager and try again."
+        ) from e
+    except FileNotFoundError as e:
+        raise RequestFailedError(
+            f"Couldn't find certificate files at '{config.backend.auth.cert_file.parent}' folder."  # pyright: ignore[reportAttributeAccessIssue]
+        ) from e
+
     # Mount the adapter for the given endpoint.
     session.mount(config.backend.endpoint, ssl_adapter)
 
diff --git a/tests/daemon/http/test_session.py b/tests/daemon/http/test_session.py
index 2bd2c19..faacab7 100644
--- a/tests/daemon/http/test_session.py
+++ b/tests/daemon/http/test_session.py
@@ -5,6 +5,7 @@
 
 from command_line_assistant.constants import VERSION
 from command_line_assistant.daemon.http.session import get_session
+from command_line_assistant.dbus.exceptions import RequestFailedError
 
 
 def test_session_headers(mock_config):
@@ -73,3 +74,26 @@ def test_various_endpoints(mock_config, endpoint):
 
     # Verify that the endpoint is used for mounting adapters
     assert any(pattern == endpoint for pattern, _ in session.adapters.items())
+
+
+def test_session_with_corrupted_ssl_certificate(mock_config):
+    mock_config.backend.auth.cert_file.write_text("whatever pem")
+    mock_config.backend.auth.key_file.write_text("whatever secret")
+    mock_config.backend.auth.verify_ssl = True
+
+    with pytest.raises(
+        RequestFailedError, match="Failed to load certificate in cert chain."
+    ):
+        get_session(mock_config)
+
+
+def test_session_with_missing_ssl_certificate(tmp_path, mock_config):
+    cert_file = tmp_path / "missing" / "cert.pem"
+    key_file = tmp_path / "missing" / "key.pem"
+
+    mock_config.backend.auth.cert_file = cert_file
+    mock_config.backend.auth.key_file = key_file
+    mock_config.backend.auth.verify_ssl = True
+
+    with pytest.raises(RequestFailedError, match="Couldn't find certificate files at"):
+        get_session(mock_config)