diff --git a/singer_sdk/typing.py b/singer_sdk/typing.py
index f2766944c..1e70f6201 100644
--- a/singer_sdk/typing.py
+++ b/singer_sdk/typing.py
@@ -825,7 +825,9 @@ def _jsonschema_type_check(jsonschema_type: dict, type_check: tuple[str]) -> boo
             if jsonschema_type.get("type") in type_check:  # noqa: PLR5501
                 return True
 
-    if any(t in type_check for t in jsonschema_type.get("anyOf", ())):
+    if any(
+        _jsonschema_type_check(t, type_check) for t in jsonschema_type.get("anyOf", ())
+    ):
         return True
 
     return False
diff --git a/tests/core/test_typing.py b/tests/core/test_typing.py
index 854669e5b..b2cf9c691 100644
--- a/tests/core/test_typing.py
+++ b/tests/core/test_typing.py
@@ -4,7 +4,9 @@
 
 import datetime
 import logging
-import typing as t
+
+import pytest
+import sqlalchemy
 
 from singer_sdk.helpers._typing import (
     TypeConformanceLevel,
@@ -17,11 +19,9 @@
     PropertiesList,
     Property,
     StringType,
+    to_sql_type,
 )
 
-if t.TYPE_CHECKING:
-    import pytest
-
 logger = logging.getLogger("log")
 
 
@@ -292,3 +292,29 @@ def test_conform_primitives():
     assert _conform_primitive_property(None, {"type": "boolean"}) is None
     assert _conform_primitive_property(0, {"type": "boolean"}) is False
     assert _conform_primitive_property(1, {"type": "boolean"}) is True
+
+
+@pytest.mark.parametrize(
+    "jsonschema_type,expected",
+    [
+        ({"type": ["string", "null"]}, sqlalchemy.types.VARCHAR),
+        ({"type": ["integer", "null"]}, sqlalchemy.types.INTEGER),
+        ({"type": ["number", "null"]}, sqlalchemy.types.DECIMAL),
+        ({"type": ["boolean", "null"]}, sqlalchemy.types.BOOLEAN),
+        ({"type": "object", "properties": {}}, sqlalchemy.types.VARCHAR),
+        ({"type": "array"}, sqlalchemy.types.VARCHAR),
+        ({"format": "date", "type": ["string", "null"]}, sqlalchemy.types.DATE),
+        ({"format": "time", "type": ["string", "null"]}, sqlalchemy.types.TIME),
+        (
+            {"format": "date-time", "type": ["string", "null"]},
+            sqlalchemy.types.DATETIME,
+        ),
+        (
+            {"anyOf": [{"type": "string", "format": "date-time"}, {"type": "null"}]},
+            sqlalchemy.types.DATETIME,
+        ),
+        ({"anyOf": [{"type": "integer"}, {"type": "null"}]}, sqlalchemy.types.INTEGER),
+    ],
+)
+def test_to_sql_type(jsonschema_type, expected):
+    assert isinstance(to_sql_type(jsonschema_type), expected)