diff --git a/python_modules/dagster/dagster/_core/definitions/declarative_automation/operators/boolean_operators.py b/python_modules/dagster/dagster/_core/definitions/declarative_automation/operators/boolean_operators.py
index d3371d110fa8e..53325ea89d847 100644
--- a/python_modules/dagster/dagster/_core/definitions/declarative_automation/operators/boolean_operators.py
+++ b/python_modules/dagster/dagster/_core/definitions/declarative_automation/operators/boolean_operators.py
@@ -2,6 +2,8 @@
 from collections.abc import Sequence
 from typing import TYPE_CHECKING, Union
 
+from typing_extensions import TypeIs
+
 import dagster._check as check
 from dagster._annotations import public
 from dagster._core.definitions.asset_key import T_EntityKey
@@ -11,6 +13,9 @@
     BuiltinAutomationCondition,
 )
 from dagster._core.definitions.declarative_automation.automation_context import AutomationContext
+from dagster._core.definitions.declarative_automation.operators.dep_operators import (
+    DepsAutomationCondition,
+)
 from dagster._record import copy, record
 from dagster._serdes.serdes import whitelist_for_serdes
 
@@ -18,6 +23,33 @@
     from dagster._core.definitions.asset_selection import AssetSelection
 
 
+def _has_allow_ignore(
+    condition: AutomationCondition,
+) -> TypeIs[
+    Union[
+        DepsAutomationCondition,
+        "AndAutomationCondition",
+        "OrAutomationCondition",
+        "NotAutomationCondition",
+    ]
+]:
+    from dagster._core.definitions.declarative_automation.operators.boolean_operators import (
+        AndAutomationCondition,
+        NotAutomationCondition,
+        OrAutomationCondition,
+    )
+
+    return isinstance(
+        condition,
+        (
+            DepsAutomationCondition,
+            AndAutomationCondition,
+            OrAutomationCondition,
+            NotAutomationCondition,
+        ),
+    )
+
+
 @whitelist_for_serdes(storage_name="AndAssetCondition")
 @record
 class AndAutomationCondition(BuiltinAutomationCondition[T_EntityKey]):
@@ -98,7 +130,7 @@ def allow(self, selection: "AssetSelection") -> "AndAutomationCondition":
         return copy(
             self,
             operands=[
-                child.allow(selection) if hasattr(child, "allow") else child
+                child.allow(selection) if _has_allow_ignore(child) else child
                 for child in self.operands
             ],
         )
@@ -118,7 +150,7 @@ def ignore(self, selection: "AssetSelection") -> "AndAutomationCondition":
         return copy(
             self,
             operands=[
-                child.ignore(selection) if hasattr(child, "ignore") else child
+                child.ignore(selection) if _has_allow_ignore(child) else child
                 for child in self.operands
             ],
         )
@@ -199,7 +231,7 @@ def allow(self, selection: "AssetSelection") -> "OrAutomationCondition":
         return copy(
             self,
             operands=[
-                child.allow(selection) if hasattr(child, "allow") else child
+                child.allow(selection) if _has_allow_ignore(child) else child
                 for child in self.operands
             ],
         )
@@ -219,7 +251,7 @@ def ignore(self, selection: "AssetSelection") -> "OrAutomationCondition":
         return copy(
             self,
             operands=[
-                child.ignore(selection) if hasattr(child, "ignore") else child
+                child.ignore(selection) if _has_allow_ignore(child) else child
                 for child in self.operands
             ],
         )
@@ -288,7 +320,7 @@ def allow(self, selection: "AssetSelection") -> "NotAutomationCondition":
         return copy(
             self,
             operand=self.operand.allow(selection)
-            if hasattr(self.operand, "allow")
+            if _has_allow_ignore(self.operand)
             else self.operand,
         )
 
@@ -307,6 +339,6 @@ def ignore(self, selection: "AssetSelection") -> "NotAutomationCondition":
         return copy(
             self,
             operand=self.operand.ignore(selection)
-            if hasattr(self.operand, "ignore")
+            if _has_allow_ignore(self.operand)
             else self.operand,
         )
diff --git a/python_modules/dagster/setup.py b/python_modules/dagster/setup.py
index 98f9cefa2d2fe..e68a16937697b 100644
--- a/python_modules/dagster/setup.py
+++ b/python_modules/dagster/setup.py
@@ -95,7 +95,7 @@ def get_version() -> str:
         "tabulate",
         "tomli<3",
         "tqdm<5",
-        "typing_extensions>=4.4.0,<5",
+        "typing_extensions>=4.10.0,<5",
         'tzdata; platform_system=="Windows"',
         "structlog",
         "sqlalchemy>=1.0,<3",