diff --git a/stix2/base.py b/stix2/base.py
index a283902..22b1128 100644
--- a/stix2/base.py
+++ b/stix2/base.py
@@ -388,11 +388,10 @@ class _Observable(_STIXBase):
                         temp_deep_copy = copy.deepcopy(dict(kwargs[key]))
                         _recursive_stix_to_dict(temp_deep_copy)
                         streamlined_obj_vals.append(temp_deep_copy)
-                    elif isinstance(kwargs[key], list) and isinstance(kwargs[key][0], _STIXBase):
-                        for obj in kwargs[key]:
-                            temp_deep_copy = copy.deepcopy(dict(obj))
-                            _recursive_stix_to_dict(temp_deep_copy)
-                            streamlined_obj_vals.append(temp_deep_copy)
+                    elif isinstance(kwargs[key], list):
+                        temp_deep_copy = copy.deepcopy(kwargs[key])
+                        _recursive_stix_list_to_dict(temp_deep_copy)
+                        streamlined_obj_vals.append(temp_deep_copy)
                     else:
                         streamlined_obj_vals.append(kwargs[key])
 
@@ -448,5 +447,20 @@ def _recursive_stix_to_dict(input_dict):
 
             # There may stil be nested _STIXBase objects
             _recursive_stix_to_dict(input_dict[key])
+        elif isinstance(input_dict[key], list):
+            _recursive_stix_list_to_dict(input_dict[key])
         else:
             return
+
+
+def _recursive_stix_list_to_dict(input_list):
+    for i in range(len(input_list)):
+        if isinstance(input_list[i], _STIXBase):
+            input_list[i] = dict(input_list[i])
+        elif isinstance(input_list[i], dict):
+            pass
+        elif isinstance(input_list[i], list):
+            _recursive_stix_list_to_dict(input_list[i])
+        else:
+            continue
+        _recursive_stix_to_dict(input_list[i])
diff --git a/stix2/test/v21/test_observed_data.py b/stix2/test/v21/test_observed_data.py
index 371018c..8254594 100644
--- a/stix2/test/v21/test_observed_data.py
+++ b/stix2/test/v21/test_observed_data.py
@@ -1574,3 +1574,47 @@ def test_ipv6_belongs_to_refs_deprecation():
             value="2001:0db8:85a3:0000:0000:8a2e:0370:7334",
             belongs_to_refs=["autonomous-system--52e0a49d-d683-5801-a7b8-145765a1e116"],
         )
+
+
+def test_id_gen_recursive_dict_conversion_1():
+    file_observable = stix2.v21.File(
+        name="example.exe",
+        size=68 * 1000,
+        magic_number_hex="50000000",
+        hashes={
+            "SHA-256": "841a8921140aba50671ebb0770fecc4ee308c4952cfeff8de154ab14eeef4649",
+        },
+        extensions={
+            "windows-pebinary-ext": stix2.v21.WindowsPEBinaryExt(
+                pe_type="exe",
+                machine_hex="014c",
+                sections=[
+                    stix2.v21.WindowsPESection(
+                        name=".data",
+                        size=4096,
+                        entropy=7.980693,
+                        hashes={"SHA-256": "6e3b6f3978e5cd96ba7abee35c24e867b7e64072e2ecb22d0ee7a6e6af6894d0"},
+                    ),
+                ],
+            ),
+        },
+    )
+
+    assert file_observable.id == "file--5219d93d-13c1-5f1f-896b-039f10ec67ea"
+
+
+def test_id_gen_recursive_dict_conversion_2():
+    wrko = stix2.v21.WindowsRegistryKey(
+        values=[
+            stix2.v21.WindowsRegistryValueType(
+                name="Foo",
+                data="qwerty",
+            ),
+            stix2.v21.WindowsRegistryValueType(
+                name="Bar",
+                data="42",
+            ),
+        ],
+    )
+
+    assert wrko.id == "windows-registry-key--c087d9fe-a03e-5922-a1cd-da116e5b8a7b"