diff --git a/rsconnect/bundle.py b/rsconnect/bundle.py
index e9790e84..df9ba659 100644
--- a/rsconnect/bundle.py
+++ b/rsconnect/bundle.py
@@ -1716,16 +1716,29 @@ def inspect_environment(
     flags: list[str] = []
     if force_generate:
         flags.append("f")
+
     args = [python, "-m", "rsconnect.environment"]
-    if len(flags) > 0:
+    if flags:
         args.append("-" + "".join(flags))
     args.append(directory)
 
     try:
-        environment_json = check_output(args, universal_newlines=True)
-    except subprocess.CalledProcessError as e:
-        raise RSConnectException("Error inspecting environment: %s" % e.output)
-    return MakeEnvironment(**json.loads(environment_json))
+        environment_json = check_output(args, text=True)
+    except Exception as e:
+        raise RSConnectException("Error inspecting environment (subprocess failed)") from e
+
+    try:
+        environment_data = json.loads(environment_json)
+    except json.JSONDecodeError as e:
+        raise RSConnectException("Error parsing environment JSON") from e
+
+    try:
+        return MakeEnvironment(**environment_data)
+    except TypeError as e:
+        system_error_message = environment_data.get("error")
+        if system_error_message:
+            raise RSConnectException(f"Error creating environment: {system_error_message}") from e
+        raise RSConnectException("Error constructing environment object") from e
 
 
 def get_python_env_info(
diff --git a/tests/test_bundle.py b/tests/test_bundle.py
index 7a2c31aa..30e727c2 100644
--- a/tests/test_bundle.py
+++ b/tests/test_bundle.py
@@ -1212,6 +1212,13 @@ def test_inspect_environment(self):
         assert environment is not None
         assert environment.python != ""
 
+    def test_inspect_environment_catches_type_error(self):
+        with pytest.raises(RSConnectException) as exec_info:
+            inspect_environment(sys.executable, None)  # type: ignore
+
+        assert isinstance(exec_info.value, RSConnectException)
+        assert isinstance(exec_info.value.__cause__, TypeError)
+
 
 @pytest.mark.parametrize(
     (