diff --git a/tests/python/test_change_system_message.py b/tests/python/test_change_system_message.py
new file mode 100644
index 000000000..1ccd6547b
--- /dev/null
+++ b/tests/python/test_change_system_message.py
@@ -0,0 +1,76 @@
+import ast
+import re
+import types
+from pathlib import Path
+
+import pytest
+
+
+def _load_change_system_message():
+    # Extract just _change_system_message from chat_templates.py so the test runs
+    # without importing unsloth (which needs unsloth_zoo / a GPU). Same pattern as
+    # tests/saving/test_is_gpt_oss_detection.py.
+    source = Path(__file__).parents[2] / "unsloth" / "chat_templates.py"
+    tree = ast.parse(source.read_text(encoding = "utf-8"))
+    funcs = [
+        node
+        for node in tree.body
+        if isinstance(node, ast.FunctionDef) and node.name == "_change_system_message"
+    ]
+    namespace = {
+        "re": re,
+        "logger": types.SimpleNamespace(warning_once = lambda *a, **k: None),
+        "DEFAULT_SYSTEM_MESSAGE": {"unsloth": "You are a helpful assistant to the user"},
+    }
+    module = ast.Module(body = funcs, type_ignores = [])
+    ast.fix_missing_locations(module)
+    exec(compile(module, str(source), "exec"), namespace)
+    return namespace["_change_system_message"]
+
+
+CUSTOM = "mycustom"  # not in DEFAULT_SYSTEM_MESSAGE -> no predefined default
+
+
+def test_custom_template_fills_placeholder():
+    # A custom template with a {system_message} placeholder must be filled, not
+    # left with the literal placeholder.
+    fn = _load_change_system_message()
+    template, used = fn("System: {system_message}\nUser:", CUSTOM, "You are a pirate")
+    assert template == "System: You are a pirate\nUser:"
+    assert "{system_message}" not in template
+    assert used == "You are a pirate"
+
+
+def test_custom_template_preserves_backslashes():
+    # Why str.replace and not re.sub: a system message with backslashes (Windows
+    # paths, LaTeX, group-like text) must be inserted verbatim. re.sub treats the
+    # replacement specially -- r"C:\Users" raises bad-escape, r"\1" is a group ref.
+    fn = _load_change_system_message()
+    for msg in (r"C:\Users\me", r"\frac{a}{b}", r"see \1 here"):
+        template, used = fn("System: {system_message}", CUSTOM, msg)
+        assert template == f"System: {msg}"
+        assert used == msg
+
+
+def test_custom_template_requires_system_message():
+    # A custom template with a placeholder but no system message must raise,
+    # rather than silently leaving the placeholder in.
+    fn = _load_change_system_message()
+    with pytest.raises(ValueError):
+        fn("System: {system_message}", CUSTOM, None)
+
+
+def test_custom_template_without_placeholder_unchanged():
+    fn = _load_change_system_message()
+    template, used = fn("System: fixed", CUSTOM, "ignored")
+    assert template == "System: fixed"
+
+
+def test_predefined_template_uses_default_then_override():
+    # Predefined templates with a default are unaffected by the change.
+    fn = _load_change_system_message()
+    t1, u1 = fn("System: {system_message}", "unsloth", None)
+    assert t1 == "System: You are a helpful assistant to the user"
+    t2, u2 = fn("System: {system_message}", "unsloth", "Custom override")
+    assert t2 == "System: Custom override"
+    assert u2 == "Custom override"
diff --git a/unsloth/chat_templates.py b/unsloth/chat_templates.py
index 7f453bff8..eba457731 100644
--- a/unsloth/chat_templates.py
+++ b/unsloth/chat_templates.py
@@ -1804,10 +1804,19 @@ CHAT_TEMPLATES["yi-chat"] = (yi_chat_template, yi_chat_template_eos_token, False
 DEFAULT_SYSTEM_MESSAGE["yi-chat"] = None
 
 def _change_system_message(template: str, type_chat_template: str, system_message: str = None):
-    system_message_pattern = r"\{system_message\}"
-
     # For predefined templates, check if default system message exists
     default_system_message = DEFAULT_SYSTEM_MESSAGE.get(f"{type_chat_template}", None)
+
+    # Custom templates have no predefined default, but may still carry a
+    # {system_message} placeholder. Handle it before the no-default early return
+    # below, which would otherwise leave the literal "{system_message}" in the
+    # template. A placeholder with no system message is an error, not a no-op.
+    if default_system_message is None and "{system_message}" in template:
+        if system_message is None:
+            raise ValueError("Unsloth: You need to provide a system message for custom templates.")
+        new_template = template.replace("{system_message}", system_message)
+        return new_template, system_message
+
     if default_system_message is None:
         if system_message is not None:
             logger.warning_once(
@@ -1817,21 +1826,9 @@ def _change_system_message(template: str, type_chat_template: str, system_messag
             )
         return template, system_message
 
-    # For custom templates
-    if type_chat_template is None:
-        has_placeholder = re.search(system_message_pattern, template) is not None
-
-        if has_placeholder:
-            if system_message is None:
-                raise ValueError("Unsloth: You need to provide a system message for custom templates.")
-            new_template = re.sub(system_message_pattern, system_message, template)
-            return new_template, system_message
-
-        return template, system_message
-
     # For predefined templates with default system message
     message_to_use = system_message if system_message is not None else default_system_message
-    new_template = re.sub(system_message_pattern, message_to_use, template)
+    new_template = template.replace("{system_message}", message_to_use)
 
     return new_template, message_to_use