diff --git a/src/bonsai/bonsai/tool/drawing.py b/src/bonsai/bonsai/tool/drawing.py
index 92f234f71d..3db1cf5851 100644
--- a/src/bonsai/bonsai/tool/drawing.py
+++ b/src/bonsai/bonsai/tool/drawing.py
@@ -456,11 +456,14 @@ class Drawing(bonsai.core.tool.Drawing):
             "PLAN_LEVEL",
         ):
             parent = ifcopenshell.util.representation.get_context(tool.Ifc.get(), "Plan")
+            if not parent:
+                parent = ifcopenshell.api.context.add_context(tool.Ifc.get(), context_type="Plan")
         else:
             parent = ifcopenshell.util.representation.get_context(tool.Ifc.get(), "Model")
+            if not parent:
+                parent = ifcopenshell.api.context.add_context(tool.Ifc.get(), context_type="Model")
 
-        return ifcopenshell.api.run(
-            "context.add_context",
+        return ifcopenshell.api.context.add_context(
             tool.Ifc.get(),
             context_type=parent.ContextType,
             context_identifier="Annotation",
diff --git a/src/bonsai/test/bim/feature/drawing.feature b/src/bonsai/test/bim/feature/drawing.feature
index ea2acdbe44..e3053280fc 100644
--- a/src/bonsai/test/bim/feature/drawing.feature
+++ b/src/bonsai/test/bim/feature/drawing.feature
@@ -134,3 +134,34 @@ Scenario: Remove drawing - deleting active drawing
     When the object "IfcAnnotation/PLAN_VIEW" is selected
     And I delete the selected objects
     Then the collection "IfcAnnotation/PLAN_VIEW" does not exist
+
+Scenario: Add annotation - text
+    Given an empty IFC project
+    And I add a cube
+    And the object "Cube" is selected
+    And I save sample test files
+    And I look at the "Drawings" panel
+    And I click "IMPORT"
+    And I click "ADD"
+    And I press "bim.expand_target_view(target_view='PLAN_VIEW')"
+    And I select the "PLAN_VIEW" item in the "BIM_UL_drawinglist" list
+    And I click "OUTLINER_OB_CAMERA"
+    When I press "bim.add_annotation"
+    Then the object "IfcAnnotation/TEXT" is selected
+
+Scenario: Add annotation - auto create context if it doesn't exist
+    Given an empty IFC project
+    And I add a cube
+    And the object "Cube" is selected
+    And I save sample test files
+    And I look at the "Geometric Representation Contexts" panel
+    And I see "Plan"
+    And I click the "X" after the text "Plan"
+    And I look at the "Drawings" panel
+    And I click "IMPORT"
+    And I click "ADD"
+    And I press "bim.expand_target_view(target_view='PLAN_VIEW')"
+    And I select the "PLAN_VIEW" item in the "BIM_UL_drawinglist" list
+    And I click "OUTLINER_OB_CAMERA"
+    When I press "bim.add_annotation"
+    Then the object "IfcAnnotation/TEXT" is selected
diff --git a/src/bonsai/test/bim/test_feature.py b/src/bonsai/test/bim/test_feature.py
index a094f94d3d..929ccc8dfa 100644
--- a/src/bonsai/test/bim/test_feature.py
+++ b/src/bonsai/test/bim/test_feature.py
@@ -134,7 +134,10 @@ class PanelSpy:
             icon = kwargs.get("icon", None)
             if text:
                 self.spied_labels.append(text)
-            spied_operator = {"operator": operator, "icon": icon, "text": text, "kwargs": {}}
+            after = ""
+            if self.spied_labels:
+                after = self.spied_labels[-1]
+            spied_operator = {"operator": operator, "icon": icon, "text": text, "kwargs": {}, "after": after}
             self.spied_operators.append(spied_operator)
             return OperatorSpy(spied_operator)
         else:
@@ -570,6 +573,22 @@ def i_click_button(button):
     assert False, f"Could not find {button}:\n{debug}"
 
 
+@given(parsers.parse('I click the "{button}" after the text "{text}"'))
+@when(parsers.parse('I click the "{button}" after the text "{text}"'))
+@then(parsers.parse('I click the "{button}" after the text "{text}"'))
+def i_click_the_button_after_the_text_text(button, text):
+    panel_spy.refresh_spy()
+    for spied_operator in panel_spy.spied_operators:
+        if spied_operator["after"] == text:
+            if spied_operator["text"] == button or spied_operator["icon"] == button:
+                spied_operator["operator"]("INVOKE_DEFAULT", **spied_operator["kwargs"])
+                panel_spy.is_spy_dirty = True
+                return
+    debug = "\n".join([f"{i} {v}" for i, v in enumerate(panel_spy.spied_operators)])
+    debug += f"\nHere is the text we see: {panel_spy.spied_labels}"
+    assert False, f"Could not find {button}:\n{debug}"
+
+
 @given(parsers.parse('I click "{button}" and expect error "{error_msg}"'))
 @when(parsers.parse('I click "{button}" and expect error "{error_msg}"'))
 def i_click_button_and_expect_error_error_msg(button, error_msg):