diff --git a/src/ifcopenshell-python/ifcopenshell/api/geometry/add_boolean.py b/src/ifcopenshell-python/ifcopenshell/api/geometry/add_boolean.py
index 31e5f9646e..105c4d4d65 100644
--- a/src/ifcopenshell-python/ifcopenshell/api/geometry/add_boolean.py
+++ b/src/ifcopenshell-python/ifcopenshell/api/geometry/add_boolean.py
@@ -18,17 +18,60 @@
 
 from __future__ import annotations
 import ifcopenshell.util.element
+from typing import Literal
 
 
 def add_boolean(
     file: ifcopenshell.file,
     first_item: ifcopenshell.entity_instance,
     second_items: list[ifcopenshell.entity_instance],
-    operator: str = "DIFFERENCE",
-) -> set[ifcopenshell.entity_instance]:
+    operator: Literal["DIFFERENCE", "INTERSECTION", "UNION"] = "DIFFERENCE",
+) -> list[ifcopenshell.entity_instance]:
+    """Adds a boolean operation to two or more representation items
+
+    If an IfcBooleanOperand is part of the top level items in an
+    IfcShapeRepresentation, it will be removed from that level whilst being
+    added to the IfcBooleanResult. This is because it is generally intuitive
+    that an item is either participating in a boolean operation, or being an
+    item in its own right, but not both.
+
+    However, if an IfcBooleanOperand is part of another boolean operation
+    already, it will not be removed from the existing operation. A new
+    operation will be created, and therefore it will participate in two
+    operations.
+
+    This function protects against recursive booleans.
+
+    After a boolean operation is made, since the items of
+    IfcShapeRepresentation may be modified, it is not guaranteed that the
+    RepresentationType is still valid. After performing all your booleans, it
+    is recommended to run :func:`ifcopenshell.api.geometry.validate_csg` to
+    ensure correctness.
+
+    :param first_item: The IfcBooleanOperand that the operation is performed upon
+    :param second_items: The IfcBooleanOperands that the operation will be
+        performed with, in the order given of the list.
+    :param operator: The type of boolean operation to perform
+    :return: A list of newly created IfcBooleanResult in the order of boolean
+        operations (based on the order of second items). If nothing was
+        created, the list will be empty.
+    """
+
+    def is_operand(item):
+        return (
+            item.is_a("IfcBooleanResult")
+            or item.is_a("IfcCsgPrimitive3D")
+            or item.is_a("IfcHalfSpaceSolid")
+            or item.is_a("IfcSolidModel")
+            or item.is_a("IfcTessellatedFaceSet")
+        )
+
+    if not is_operand(first_item):
+        return []
+
     original_first_item = first_item
-    if first_item in second_items:
-        second_items.remove(first_item)
+
+    second_items = [i for i in second_items if i != first_item and is_operand(i)]
 
     while True:
         is_part_of_boolean = False
@@ -45,20 +88,16 @@ def add_boolean(
             break
 
     if not second_items:
-        return
+        return []
 
     # Don't replace style or aspect relationships.
     to_replace = set(
-        [
-            i
-            for i in file.get_inverse(first_item)
-            if i.is_a("IfcShapeRepresentation") or i.is_a("IfcBooleanResult")
-        ]
+        [i for i in file.get_inverse(first_item) if i.is_a("IfcShapeRepresentation") or i.is_a("IfcBooleanResult")]
     )
 
     first = first_item
 
-    booleans = set()
+    booleans = []
     for second_item in second_items:
         for inverse in file.get_inverse(second_item):
             if inverse.is_a("IfcShapeRepresentation"):
@@ -68,7 +107,7 @@ def add_boolean(
         if second_item.is_a("IfcTesselatedFaceSet"):
             second_item.Closed = True  # For now, trust the user to do the right thing.
         first = file.create_entity("IfcBooleanResult", operator, first, second_item)
-        booleans.add(first)
+        booleans.append(first)
 
     for inverse in to_replace:
         ifcopenshell.util.element.replace_attribute(inverse, first_item, first)
diff --git a/src/ifcopenshell-python/test/api/geometry/test_add_boolean.py b/src/ifcopenshell-python/test/api/geometry/test_add_boolean.py
index 584099fc62..ba8385fa3e 100644
--- a/src/ifcopenshell-python/test/api/geometry/test_add_boolean.py
+++ b/src/ifcopenshell-python/test/api/geometry/test_add_boolean.py
@@ -59,7 +59,6 @@ class TestAddBoolean(test.bootstrap.IFC4):
         assert len(booleans) == 2
         assert len(rep.Items) == 1
         assert rep.Items[0].FirstOperand.is_a("IfcBooleanResult")
-        assert rep.Items[0].FirstOperand.is_a("IfcBooleanResult")
         assert rep.Items[0].SecondOperand == second2
         assert rep.Items[0].Operator == "DIFFERENCE"
         assert rep.Items[0].FirstOperand.FirstOperand == first