diff --git a/dspy/signatures/signature.py b/dspy/signatures/signature.py
index 0121de9ea7..455522d836 100644
--- a/dspy/signatures/signature.py
+++ b/dspy/signatures/signature.py
@@ -45,6 +45,8 @@ def __call__(cls, *args, **kwargs):  # noqa: ANN002
         return super().__call__(*args, **kwargs)
 
     def __new__(mcs, signature_name, bases, namespace, **kwargs):  # noqa: N804
+        # At this point, the orders have been swapped already.
+        field_order = [name for name, value in namespace.items() if isinstance(value, FieldInfo)]
         # Set `str` as the default type for all fields
         raw_annotations = namespace.get("__annotations__", {})
         for name, field in namespace.items():
@@ -52,7 +54,11 @@ def __new__(mcs, signature_name, bases, namespace, **kwargs):  # noqa: N804
                 continue  # Don't add types to non-field attributes
             if not name.startswith("__") and name not in raw_annotations:
                 raw_annotations[name] = str
-        namespace["__annotations__"] = raw_annotations
+        # Create ordered annotations dictionary that preserves field order
+        ordered_annotations = {name: raw_annotations[name] for name in field_order if name in raw_annotations}
+        # Add any remaining annotations that weren't in field_order
+        ordered_annotations.update({k: v for k, v in raw_annotations.items() if k not in ordered_annotations})
+        namespace["__annotations__"] = ordered_annotations
 
         # Let Pydantic do its thing
         cls = super().__new__(mcs, signature_name, bases, namespace, **kwargs)
diff --git a/tests/predict/test_parallel.py b/tests/predict/test_parallel.py
index 072aa7eb1a..1c3a932fb0 100644
--- a/tests/predict/test_parallel.py
+++ b/tests/predict/test_parallel.py
@@ -71,26 +71,18 @@ def forward(self, input):
             res2 = self.predictor2.batch([input] * 5)
 
             return (res1, res2)
-        
-    result, reason_result = MyModule()(dspy.Example(input="test input").with_inputs("input"))
 
-    assert result[0].output == "test output 1"
-    assert result[1].output == "test output 2"
-    assert result[2].output == "test output 3"
-    assert result[3].output == "test output 4"
-    assert result[4].output == "test output 5"
+    result, reason_result = MyModule()(dspy.Example(input="test input").with_inputs("input"))
 
-    assert reason_result[0].output == "test output 1"
-    assert reason_result[1].output == "test output 2"
-    assert reason_result[2].output == "test output 3"
-    assert reason_result[3].output == "test output 4"
-    assert reason_result[4].output == "test output 5"
+    # Check that we got all expected outputs without caring about order
+    expected_outputs = {f"test output {i}" for i in range(1, 6)}
+    assert {r.output for r in result} == expected_outputs
+    assert {r.output for r in reason_result} == expected_outputs
 
-    assert reason_result[0].reasoning == "test reasoning 1"
-    assert reason_result[1].reasoning == "test reasoning 2"
-    assert reason_result[2].reasoning == "test reasoning 3"
-    assert reason_result[3].reasoning == "test reasoning 4"
-    assert reason_result[4].reasoning == "test reasoning 5"
+    # Check that reasoning matches outputs for reason_result
+    for r in reason_result:
+        num = r.output.split()[-1]  # get the number from "test output X"
+        assert r.reasoning == f"test reasoning {num}"
 
 
 def test_nested_parallel_module():
@@ -120,7 +112,7 @@ def forward(self, input):
                     (self.predictor, input),
                 ]),
             ])
-        
+
     output = MyModule()(dspy.Example(input="test input").with_inputs("input"))
 
     assert output[0].output == "test output 1"
@@ -148,7 +140,7 @@ def forward(self, input):
             res = self.predictor.batch([dspy.Example(input=input).with_inputs("input")]*2)
 
             return res
-        
+
     result = MyModule().batch([dspy.Example(input="test input").with_inputs("input")]*2)
 
     assert {result[0][0].output, result[0][1].output, result[1][0].output, result[1][1].output} \
diff --git a/tests/signatures/test_signature.py b/tests/signatures/test_signature.py
index 864a574a71..136fac213b 100644
--- a/tests/signatures/test_signature.py
+++ b/tests/signatures/test_signature.py
@@ -151,6 +151,17 @@ class InitialSignature(Signature):
     assert "new_output_end" == list(S4.output_fields.keys())[-1]
 
 
+def test_order_preserved_with_mixed_annotations():
+    class ExampleSignature(dspy.Signature):
+        text: str = dspy.InputField()
+        output = dspy.OutputField()
+        pass_evaluation: bool = dspy.OutputField()
+
+    expected_order = ["text", "output", "pass_evaluation"]
+    actual_order = list(ExampleSignature.fields.keys())
+    assert actual_order == expected_order
+
+
 def test_infer_prefix():
     assert infer_prefix("someAttributeName42IsCool") == "Some Attribute Name 42 Is Cool"
     assert infer_prefix("version2Update") == "Version 2 Update"