diff --git a/linodecli/baked/operation.py b/linodecli/baked/operation.py
index 5a5ec7c0..d802d4ed 100644
--- a/linodecli/baked/operation.py
+++ b/linodecli/baked/operation.py
@@ -455,20 +455,31 @@ def _handle_list_items(
         parsed,
     ):  # pylint: disable=too-many-locals,too-many-branches,too-many-statements
         lists = {}
+
         # group list items as expected
         for arg_name, list_name in list_items:
             item_name = arg_name.split(list_name)[1][1:]
+
             if hasattr(parsed, arg_name):
                 val = getattr(parsed, arg_name) or []
                 if not val:
                     continue
+
                 if list_name not in lists:
-                    new_list = [{item_name: c} for c in val]
-                    lists[list_name] = new_list
-                else:
-                    update_list = lists[list_name]
-                    for obj, item in zip(update_list, val):
-                        obj[item_name] = item
+                    lists[list_name] = []
+
+                target_list = lists[list_name]
+
+                # If there are any additional indices not accounted for
+                # in the target list, add new objects accordingly.
+                if len(target_list) < len(val):
+                    for _ in range(len(val) - len(target_list)):
+                        target_list.append({})
+
+                # Populate each entry in the target list
+                # with each corresponding entry in val.
+                for obj, item in zip(target_list, val):
+                    obj[item_name] = item
 
         # break out list items with periods in their name into objects.  This
         # allows supporting nested lists
diff --git a/tests/fixtures/api_request_test_foobar_post.yaml b/tests/fixtures/api_request_test_foobar_post.yaml
index 5a1284ab..f1001eb8 100644
--- a/tests/fixtures/api_request_test_foobar_post.yaml
+++ b/tests/fixtures/api_request_test_foobar_post.yaml
@@ -97,3 +97,16 @@ components:
           type: number
           nullable: true
           description: An arbitrary nullable float
+        object_list:
+          type: array
+          description: An arbitrary list of objects.
+          items:
+            type: object
+            description: An arbitrary object.
+            properties:
+              field_string:
+                type: string
+                description: An arbitrary field.
+              field_int:
+                type: number
+                description: An arbitrary field.
diff --git a/tests/unit/test_operation.py b/tests/unit/test_operation.py
index 8bb9fa8a..ed047417 100644
--- a/tests/unit/test_operation.py
+++ b/tests/unit/test_operation.py
@@ -159,6 +159,27 @@ def test_parse_args_nullable_float(self, create_operation):
         result = create_operation.parse_args(["--nullable_float", "456.123"])
         assert result.nullable_float == 456.123
 
+    def test_parse_args_object_list(self, create_operation):
+        result = create_operation.parse_args(
+            [
+                "--object_list.field_string",
+                "test1",
+                "--object_list.field_int",
+                "123",
+                "--object_list.field_int",
+                "456",
+            ]
+        )
+        assert result.object_list == [
+            {
+                "field_string": "test1",
+                "field_int": 123,
+            },
+            {
+                "field_int": 456,
+            },
+        ]
+
     def test_array_arg_action_basic(self):
         """
         Tests a basic array argument condition..