diff --git a/src/sparseml/export/validators.py b/src/sparseml/export/validators.py
index 52c9fa05ee0..f513bda21aa 100644
--- a/src/sparseml/export/validators.py
+++ b/src/sparseml/export/validators.py
@@ -17,8 +17,9 @@
 import os.path
 from collections import OrderedDict
 from pathlib import Path
-from typing import Callable, List, Optional, Union
+from typing import Callable, List, Optional
 from typing import OrderedDict as OrderedDictType
+from typing import Union
 
 import numpy
 import onnx
diff --git a/src/sparseml/transformers/utils/helpers.py b/src/sparseml/transformers/utils/helpers.py
index 9cc4481c694..48aec7f763a 100644
--- a/src/sparseml/transformers/utils/helpers.py
+++ b/src/sparseml/transformers/utils/helpers.py
@@ -559,7 +559,7 @@ def fetch_recipe_path(target: str):
     return recipe_path
 
 
-def generate_mask(string: str, response: str, prompt: Optional[str] = None) -> str:
+def generate_mask(string: str, response: str, prompt: str = "") -> str:
     """
     Generate a mask based on provided prompt and response strings to obscure
     characters in the input string. Prompt will be masked and string in response
@@ -576,18 +576,16 @@ def generate_mask(string: str, response: str, prompt: Optional[str] = None) -> s
         characters and '0' indicates obscured characters.
 
     """
-    if prompt is None:
-        prompt = ""
 
     mask = ["1"] * len(string)
-    is_prompt = True
+    is_prompt = False if string.startswith(response) else True
     counter = 0
     for i, char in enumerate(string):
         if is_prompt:
             mask[i] = "0"
 
         if counter > 0:
-            if not is_prompt and char == prompt[counter]:
+            if not is_prompt and len(prompt) > 1 and char == prompt[counter]:
                 counter += 1
             elif is_prompt and char == response[counter]:
                 counter += 1
diff --git a/tests/sparseml/transformers/finetune/test_finetune.py b/tests/sparseml/transformers/finetune/test_finetune.py
index b2a437751da..aa9f84e02b1 100644
--- a/tests/sparseml/transformers/finetune/test_finetune.py
+++ b/tests/sparseml/transformers/finetune/test_finetune.py
@@ -32,6 +32,7 @@
     oneshot,
     train,
 )
+from sparseml.transformers.utils.helpers import generate_mask
 
 
 def test_oneshot_and_finetune(tmp_path: Path):
@@ -319,3 +320,35 @@ def test_oneshot_with_modifier_object(tmp_path: Path):
         splits=splits,
         oneshot_device=device,
     )
+
+
+def test_finetune_wout_recipe_with_mask(tmp_path: Path):
+    recipe_str = None
+    model = "Xenova/llama2.c-stories15M"
+    device = "cuda:0"
+    if not torch.cuda.is_available():
+        device = "cpu"
+    dataset = "open_platypus"
+    concatenate_data = False
+    output_dir = tmp_path
+    max_steps = 50
+    splits = "train"
+
+    def preprocessing_func(example):
+        example["text"] = "[foo]" + example["text"] + "[bar] mask this"
+        example["mask"] = generate_mask(
+            example["text"], response="[bar]", prompt="[foo]"
+        )
+        return example
+
+    train(
+        model=model,
+        dataset=dataset,
+        output_dir=output_dir,
+        recipe=recipe_str,
+        max_steps=max_steps,
+        concatenate_data=concatenate_data,
+        splits=splits,
+        oneshot_device=device,
+        preprocessing_func=preprocessing_func,
+    )
diff --git a/tests/sparseml/transformers/utils/test_helpers.py b/tests/sparseml/transformers/utils/test_helpers.py
index 0d77a6ee7d2..04ebf735d7e 100644
--- a/tests/sparseml/transformers/utils/test_helpers.py
+++ b/tests/sparseml/transformers/utils/test_helpers.py
@@ -206,7 +206,16 @@ def test_save_zoo_directory(tmp_path, stub):
             None,
             ("0000000" "1111111111"),
         ),
+        (
+            ("[bar]world" "[foo]hello\n\n" "[bar]world"),
+            "[bar]",
+            "[foo]",
+            ("1111111111" "000000000000" "1111111111"),
+        ),
     ],
 )
 def test_generate_mask(string, response, prompt, expected_mask):
-    assert generate_mask(string, response, prompt) == expected_mask
+    if prompt is not None:
+        assert generate_mask(string, response, prompt) == expected_mask
+    else:
+        assert generate_mask(string, response) == expected_mask