diff --git a/src/lob_hlpr/hlpr.py b/src/lob_hlpr/hlpr.py
index 1851499..087d914 100644
--- a/src/lob_hlpr/hlpr.py
+++ b/src/lob_hlpr/hlpr.py
@@ -166,8 +166,53 @@ def lob_print(log_path: str, *args, **kwargs):
 
     @staticmethod
     def ascleandict(dclass, remove_false=False):
-        """Convert a dataclass to a dictionary and remove None values."""
-        return asdict(
+        """Convert a dataclass to a dictionary and remove None values.
+
+        Largely generated by AI...
+
+        Args:
+            dclass: The dataclass instance to convert.
+            remove_false: If True, also remove boolean fields that are False.
+
+        Returns:
+            dict: The cleaned dictionary without empty values.
+        """
+
+        def clean_value(v):
+            """Recursively clean nested structures."""
+            if isinstance(v, dict):
+                cleaned = {
+                    k: clean_value(val)
+                    for (k, val) in v.items()
+                    if (val is not None)
+                    and not (isinstance(val, list) and len(val) == 0)
+                    and not (isinstance(val, dict) and len(val) == 0)
+                    and not (remove_false and (isinstance(val, bool) and val is False))
+                }
+                # Keep removing empty dicts/lists until nothing changes
+                while True:
+                    filtered = {
+                        k: v
+                        for (k, v) in cleaned.items()
+                        if not (isinstance(v, dict) and len(v) == 0)
+                        and not (isinstance(v, list) and len(v) == 0)
+                    }
+                    if len(filtered) == len(cleaned):
+                        break
+                    cleaned = filtered
+                return cleaned
+            elif isinstance(v, list):
+                cleaned_items = [clean_value(item) for item in v]
+                # Filter out empty dicts and lists from the result
+                return [
+                    item
+                    for item in cleaned_items
+                    if not (isinstance(item, dict) and len(item) == 0)
+                    and not (isinstance(item, list) and len(item) == 0)
+                ]
+            return v
+
+        result = asdict(
             dclass,
             dict_factory=lambda x: {
                 k: v
@@ -178,6 +223,7 @@ def ascleandict(dclass, remove_false=False):
                 and not (remove_false and (isinstance(v, bool) and v is False))
             },
         )
+        return clean_value(result)
 
     @staticmethod
     def unix_timestamp() -> int:
diff --git a/tests/test_lob_hlpr.py b/tests/test_lob_hlpr.py
index 8d6570c..2256734 100644
--- a/tests/test_lob_hlpr.py
+++ b/tests/test_lob_hlpr.py
@@ -161,9 +161,14 @@ def test_log_print_passes(tmp_path, capsys):
 def test_as_clean_dict_passes():
     """Test as_clean_dict function with valid inputs."""
 
+    @dataclass
+    class MoreNestedTestClass:
+        listkey: list | None = None
+        dictkey: dict | None = None
+
     @dataclass
     class NestedTestClass:
-        nested_key: str | None = None
+        more_nested: MoreNestedTestClass | None = None
 
     @dataclass
     class TestClass:
@@ -184,10 +189,58 @@ class TestClass:
     dclass.dictkey = {}
     dclass.boolkey = False
     dclass.nested = NestedTestClass()
+    dclass.nested.more_nested = MoreNestedTestClass(dictkey={}, listkey=[])
     assert hlp.ascleandict(dclass) == {"intkey": 0, "strkey": "", "boolkey": False}
+    assert "nested" not in hlp.ascleandict(dclass)
 
     assert hlp.ascleandict(dclass, remove_false=True) == {"intkey": 0, "strkey": ""}
 
+    @dataclass
+    class DataWithList:
+        items: list
+        name: str
+
+    data2 = DataWithList(
+        items=[{"value": 1, "empty_dict": {}}, {"value": 2, "none_val": None}, [], {}],
+        name="test",
+    )
+    result2 = hlp.ascleandict(data2)
+    assert result2 == {"name": "test", "items": [{"value": 1}, {"value": 2}]}
+
+
+def test_ascleandict_nested_cleanup_multiple_passes():
+    """Test that ascleandict removes cascading empty nested structures."""
+
+    @dataclass
+    class DeepNested:
+        value: str | None = None
+
+    @dataclass
+    class MidLevel:
+        deep: DeepNested | None = None
+        data: dict | None = None
+
+    @dataclass
+    class TopLevel:
+        mid: MidLevel | None = None
+        name: str = "test"
+
+    # Create data where cleaning cascades:
+    # - DeepNested.value = None gets removed
+    # - MidLevel.deep becomes {} and gets removed
+    # - MidLevel.data is already {} and gets removed
+    # - MidLevel itself might become {} and gets removed
+    data = TopLevel(
+        name="test",
+        mid=MidLevel(
+            deep=DeepNested(value=None),  # Becomes {}
+            data={"inner": None},  # Becomes {}
+        ),
+    )
+    result = hlp.ascleandict(data)
+    # The while loop should run multiple times, executing line 190
+    assert result == {"name": "test"}
+
 
 def test_unix_timestamp():
     """Test unix_timestamp function."""