diff --git a/src/azure-cli-core/azure/cli/core/util.py b/src/azure-cli-core/azure/cli/core/util.py
index 3d5e16758d5..638d13d9380 100644
--- a/src/azure-cli-core/azure/cli/core/util.py
+++ b/src/azure-cli-core/azure/cli/core/util.py
@@ -58,7 +58,7 @@ def handle_exception(ex):  # pylint: disable=too-many-locals, too-many-statement
     from msrestazure.azure_exceptions import CloudError
     from msrest.exceptions import HttpOperationError, ValidationError, ClientRequestError
     from azure.common import AzureException
-    from azure.core.exceptions import AzureError
+    from azure.core.exceptions import AzureError, ServiceRequestError
     from requests.exceptions import SSLError, HTTPError
     from azure.cli.core import azclierror
     from msal_extensions.persistence import PersistenceError
@@ -79,7 +79,11 @@ def handle_exception(ex):  # pylint: disable=too-many-locals, too-many-statement
         az_error = azclierror.InvalidArgumentValueError(error_msg)
         az_error.set_recommendation(QUERY_REFERENCE)
 
-    elif isinstance(ex, SSLError):
+    # SSLError is raised when making HTTP requests with 'requests' lib behind a proxy that intercepts HTTPS traffic.
+    # - SSLError is raised when directly calling 'requests' lib, such as MSAL or `az rest`
+    # - azure.core.exceptions.ServiceRequestError is raised when indirectly calling 'requests' lib with azure.core,
+    #   which wraps the original SSLError
+    elif isinstance(ex, SSLError) or isinstance(ex, ServiceRequestError) and isinstance(ex.inner_exception, SSLError):
         az_error = azclierror.AzureConnectionError(error_msg)
         az_error.set_recommendation(SSLERROR_TEMPLATE)