diff --git a/pyrit/executor/attack/component/conversation_manager.py b/pyrit/executor/attack/component/conversation_manager.py
index 439f93ac49..e48faa6666 100644
--- a/pyrit/executor/attack/component/conversation_manager.py
+++ b/pyrit/executor/attack/component/conversation_manager.py
@@ -308,9 +308,10 @@ async def initialize_context_async(
             - All messages get new UUIDs
 
         For non-chat PromptTarget:
-            - If `config.non_chat_target_behavior="normalize_first_turn"`: normalizes
-              conversation to string and prepends to context.next_message
-            - If `config.non_chat_target_behavior="raise"`: raises ValueError
+            - Normalizes the prepended conversation to a string and prepends it to
+              ``context.next_message`` (using ``config.message_normalizer`` when provided).
+            - If the deprecated ``config.non_chat_target_behavior="raise"`` is set,
+              raises ValueError instead. This option is deprecated and will be removed in v0.16.0.
 
         Args:
             context: The attack context to initialize.
@@ -390,11 +391,11 @@ async def _handle_non_chat_target_async(
         if config.non_chat_target_behavior == "raise":
             raise ValueError(
                 "prepended_conversation requires the objective target to support multi-turn "
-                "conversations with editable history. The current target does not. "
-                "Use PrependedConversationConfig with non_chat_target_behavior='normalize_first_turn' "
-                "to normalize the conversation into the first message instead."
+                "conversations with editable history. The current target does not. Note that "
+                "the non_chat_target_behavior parameter is deprecated and will be removed in "
+                "v0.16.0; non-chat targets will then always normalize the prepended conversation "
+                "into the first turn."
             )
-
         # Normalize conversation to string
         normalizer = config.get_message_normalizer()
         normalized_context = await normalizer.normalize_string_async(prepended_conversation)
diff --git a/pyrit/executor/attack/component/prepended_conversation_config.py b/pyrit/executor/attack/component/prepended_conversation_config.py
index fddeae5371..13c236cef6 100644
--- a/pyrit/executor/attack/component/prepended_conversation_config.py
+++ b/pyrit/executor/attack/component/prepended_conversation_config.py
@@ -3,9 +3,11 @@
 
 from __future__ import annotations
 
+import warnings
 from dataclasses import dataclass, field
-from typing import Literal, Optional, get_args
+from typing import Literal, get_args
 
+from pyrit.common.deprecation import print_deprecation_message
 from pyrit.message_normalizer import (
     ConversationContextNormalizer,
     MessageStringNormalizer,
@@ -34,16 +36,25 @@ class PrependedConversationConfig:
     # Must implement MessageStringNormalizer (e.g., TokenizerTemplateNormalizer or ConversationContextNormalizer).
     # When None and normalization is needed (e.g., for non-chat targets), a default
     # ConversationContextNormalizer is used that produces "Turn N: User/Assistant" format.
-    message_normalizer: Optional[MessageStringNormalizer] = None
-
-    # Behavior when the target is a PromptTarget but not a chat-capable PromptTarget:
-    # - "normalize_first_turn": Normalize the prepended conversation into a string and
-    #   store it in ConversationState.normalized_prepended_context. This context will be
-    #   prepended to the first message sent to the target. Uses objective_target_context_normalizer
-    #   if provided, otherwise falls back to ConversationContextNormalizer.
-    # - "raise": Raise a ValueError. Use this when prepended conversation history must be
-    #   maintained by the target (i.e., target must be a chat-capable PromptTarget).
-    non_chat_target_behavior: Literal["normalize_first_turn", "raise"] = "normalize_first_turn"
+    message_normalizer: MessageStringNormalizer | None = None
+
+    # Deprecated: this option will be removed in v0.16.0. Setting this field to any
+    # non-None value emits a DeprecationWarning. In this release, ``"raise"`` still
+    # raises ValueError on non-chat targets; ``"normalize_first_turn"`` and ``None``
+    # both normalize the prepended conversation into the first turn (via
+    # ``message_normalizer``; default: ConversationContextNormalizer). In v0.16.0
+    # non-chat targets will always normalize; there is no replacement for the
+    # ``"raise"`` behavior.
+    non_chat_target_behavior: Literal["normalize_first_turn", "raise"] | None = None
+
+    def __post_init__(self) -> None:
+        """Emit a DeprecationWarning when the deprecated ``non_chat_target_behavior`` field is set."""
+        if self.non_chat_target_behavior is not None:
+            print_deprecation_message(
+                old_item="PrependedConversationConfig(non_chat_target_behavior=...)",
+                new_item="PrependedConversationConfig() (non-chat targets always normalize the prepended conversation)",
+                removed_in="0.16.0",
+            )
 
     def get_message_normalizer(self) -> MessageStringNormalizer:
         """
@@ -58,30 +69,44 @@ def get_message_normalizer(self) -> MessageStringNormalizer:
     @classmethod
     def default(cls) -> PrependedConversationConfig:
         """
-        Create a default configuration with converters applied to all roles.
+        Return a deprecated configuration with ``non_chat_target_behavior="raise"``.
+
+        .. deprecated::
+            ``default()`` is deprecated and will be removed in v0.16.0. Use
+            ``PrependedConversationConfig()`` instead. In this release the returned
+            configuration still raises on non-chat targets; in v0.16.0 the ``"raise"``
+            branch is removed and non-chat targets will always normalize the prepended
+            conversation into the first turn.
 
         Returns:
-            A configuration that applies converters to all prepended messages,
-            raising an error for non-chat targets.
+            A configuration equivalent to ``PrependedConversationConfig(non_chat_target_behavior="raise")``.
         """
-        return cls(
-            apply_converters_to_roles=list(get_args(ChatMessageRole)),
-            message_normalizer=None,
-            non_chat_target_behavior="raise",
+        print_deprecation_message(
+            old_item="PrependedConversationConfig.default()",
+            new_item="PrependedConversationConfig() (non-chat targets always normalize the prepended conversation)",
+            removed_in="0.16.0",
         )
+        # Suppress the __post_init__ deprecation warning so callers see exactly
+        # one warning (the one for default()) rather than two for a single deprecated call.
+        with warnings.catch_warnings():
+            warnings.simplefilter("ignore", DeprecationWarning)
+            return cls(non_chat_target_behavior="raise")
 
     @classmethod
     def for_non_chat_target(
         cls,
         *,
-        message_normalizer: Optional[MessageStringNormalizer] = None,
-        apply_converters_to_roles: Optional[list[ChatMessageRole]] = None,
+        message_normalizer: MessageStringNormalizer | None = None,
+        apply_converters_to_roles: list[ChatMessageRole] | None = None,
     ) -> PrependedConversationConfig:
         """
         Create a configuration for use with non-chat targets.
 
-        This configuration normalizes the prepended conversation into a text block
-        that will be prepended to the first message sent to the target.
+        .. deprecated::
+            ``for_non_chat_target()`` is deprecated and will be removed in v0.16.0.
+            Non-chat targets always normalize the prepended conversation into the
+            first turn, so this factory is equivalent to ``PrependedConversationConfig(...)``
+            with the same arguments. Use the default constructor instead.
 
         Args:
             message_normalizer: Normalizer for formatting the prepended conversation into a string.
@@ -92,10 +117,21 @@ def for_non_chat_target(
         Returns:
             A configuration that normalizes the prepended conversation for non-chat targets.
         """
-        return cls(
-            apply_converters_to_roles=(
-                apply_converters_to_roles if apply_converters_to_roles is not None else list(get_args(ChatMessageRole))
-            ),
-            message_normalizer=message_normalizer,
-            non_chat_target_behavior="normalize_first_turn",
+        print_deprecation_message(
+            old_item="PrependedConversationConfig.for_non_chat_target()",
+            new_item="PrependedConversationConfig() (non-chat targets always normalize the prepended conversation)",
+            removed_in="0.16.0",
         )
+        # Suppress the __post_init__ deprecation warning so callers see exactly one
+        # warning (the one for for_non_chat_target()) rather than two.
+        with warnings.catch_warnings():
+            warnings.simplefilter("ignore", DeprecationWarning)
+            return cls(
+                apply_converters_to_roles=(
+                    apply_converters_to_roles
+                    if apply_converters_to_roles is not None
+                    else list(get_args(ChatMessageRole))
+                ),
+                message_normalizer=message_normalizer,
+                non_chat_target_behavior="normalize_first_turn",
+            )
diff --git a/tests/unit/executor/attack/component/test_conversation_manager.py b/tests/unit/executor/attack/component/test_conversation_manager.py
index c0bae706b5..a83bbe1968 100644
--- a/tests/unit/executor/attack/component/test_conversation_manager.py
+++ b/tests/unit/executor/attack/component/test_conversation_manager.py
@@ -838,7 +838,7 @@ async def test_normalizes_for_non_chat_target_when_configured(
         context.prepended_conversation = sample_conversation
         context.next_message = Message.from_prompt(prompt="Next message", role="user")
 
-        config = PrependedConversationConfig(non_chat_target_behavior="normalize_first_turn")
+        config = PrependedConversationConfig()
 
         await manager.initialize_context_async(
             context=context,
@@ -1088,7 +1088,8 @@ async def test_non_chat_target_behavior_raise_explicit(
         context = _TestAttackContext(params=AttackParameters(objective="Test objective"))
         context.prepended_conversation = sample_conversation
 
-        config = PrependedConversationConfig(non_chat_target_behavior="raise")
+        with pytest.warns(DeprecationWarning, match="non_chat_target_behavior"):
+            config = PrependedConversationConfig(non_chat_target_behavior="raise")
 
         with pytest.raises(
             ValueError,
@@ -1115,7 +1116,7 @@ async def test_non_chat_target_behavior_normalize_first_turn_creates_next_messag
         context.prepended_conversation = sample_conversation
         context.next_message = None
 
-        config = PrependedConversationConfig(non_chat_target_behavior="normalize_first_turn")
+        config = PrependedConversationConfig()
 
         await manager.initialize_context_async(
             context=context,
@@ -1142,7 +1143,7 @@ async def test_non_chat_target_behavior_normalize_first_turn_prepends_to_existin
         context.prepended_conversation = sample_conversation
         context.next_message = Message.from_prompt(prompt="My question", role="user")
 
-        config = PrependedConversationConfig(non_chat_target_behavior="normalize_first_turn")
+        config = PrependedConversationConfig()
 
         await manager.initialize_context_async(
             context=context,
@@ -1170,7 +1171,7 @@ async def test_non_chat_target_behavior_normalize_returns_empty_state(
         context = _TestAttackContext(params=AttackParameters(objective="Test objective"))
         context.prepended_conversation = sample_conversation
 
-        config = PrependedConversationConfig(non_chat_target_behavior="normalize_first_turn")
+        config = PrependedConversationConfig()
 
         state = await manager.initialize_context_async(
             context=context,
@@ -1314,7 +1315,7 @@ async def test_message_normalizer_default_uses_conversation_context_normalizer(
         context.prepended_conversation = sample_conversation
         context.next_message = None
 
-        config = PrependedConversationConfig(non_chat_target_behavior="normalize_first_turn")
+        config = PrependedConversationConfig()
 
         await manager.initialize_context_async(
             context=context,
@@ -1348,7 +1349,6 @@ async def test_message_normalizer_custom_normalizer_is_used(
         context.next_message = None
 
         config = PrependedConversationConfig(
-            non_chat_target_behavior="normalize_first_turn",
             message_normalizer=mock_normalizer,
         )
 
@@ -1372,7 +1372,8 @@ async def test_message_normalizer_custom_normalizer_is_used(
 
     def test_default_factory_creates_raise_behavior(self) -> None:
         """Test that PrependedConversationConfig.default() creates raise behavior."""
-        config = PrependedConversationConfig.default()
+        with pytest.warns(DeprecationWarning, match="PrependedConversationConfig.default\\(\\) is deprecated"):
+            config = PrependedConversationConfig.default()
 
         assert config.non_chat_target_behavior == "raise"
         assert config.message_normalizer is None
@@ -1383,7 +1384,10 @@ def test_default_factory_creates_raise_behavior(self) -> None:
 
     def test_for_non_chat_target_factory_creates_normalize_behavior(self) -> None:
         """Test that for_non_chat_target() creates normalize_first_turn behavior."""
-        config = PrependedConversationConfig.for_non_chat_target()
+        with pytest.warns(
+            DeprecationWarning, match="PrependedConversationConfig.for_non_chat_target\\(\\) is deprecated"
+        ):
+            config = PrependedConversationConfig.for_non_chat_target()
 
         assert config.non_chat_target_behavior == "normalize_first_turn"
 
@@ -1392,14 +1396,20 @@ def test_for_non_chat_target_with_custom_normalizer(self) -> None:
         from pyrit.message_normalizer import MessageStringNormalizer
 
         mock_normalizer = MagicMock(spec=MessageStringNormalizer)
-        config = PrependedConversationConfig.for_non_chat_target(message_normalizer=mock_normalizer)
+        with pytest.warns(
+            DeprecationWarning, match="PrependedConversationConfig.for_non_chat_target\\(\\) is deprecated"
+        ):
+            config = PrependedConversationConfig.for_non_chat_target(message_normalizer=mock_normalizer)
 
         assert config.message_normalizer == mock_normalizer
         assert config.non_chat_target_behavior == "normalize_first_turn"
 
     def test_for_non_chat_target_with_custom_roles(self) -> None:
         """Test that for_non_chat_target() accepts custom apply_converters_to_roles."""
-        config = PrependedConversationConfig.for_non_chat_target(apply_converters_to_roles=["user"])
+        with pytest.warns(
+            DeprecationWarning, match="PrependedConversationConfig.for_non_chat_target\\(\\) is deprecated"
+        ):
+            config = PrependedConversationConfig.for_non_chat_target(apply_converters_to_roles=["user"])
 
         assert config.apply_converters_to_roles == ["user"]
         assert config.non_chat_target_behavior == "normalize_first_turn"
@@ -1421,7 +1431,8 @@ async def test_chat_target_ignores_non_chat_target_behavior(
         context.prepended_conversation = sample_conversation
 
         # Even with raise behavior, chat targets should work
-        config = PrependedConversationConfig(non_chat_target_behavior="raise")
+        with pytest.warns(DeprecationWarning, match="non_chat_target_behavior"):
+            config = PrependedConversationConfig(non_chat_target_behavior="raise")
 
         state = await manager.initialize_context_async(
             context=context,
diff --git a/tests/unit/executor/attack/component/test_prepended_conversation_config.py b/tests/unit/executor/attack/component/test_prepended_conversation_config.py
index fd6ed9038e..2b08a26c51 100644
--- a/tests/unit/executor/attack/component/test_prepended_conversation_config.py
+++ b/tests/unit/executor/attack/component/test_prepended_conversation_config.py
@@ -4,6 +4,8 @@
 from typing import get_args
 from unittest.mock import MagicMock
 
+import pytest
+
 from pyrit.executor.attack.component.prepended_conversation_config import PrependedConversationConfig
 from pyrit.message_normalizer import ConversationContextNormalizer
 from pyrit.models import ChatMessageRole
@@ -21,7 +23,7 @@ def test_default_init_message_normalizer_is_none():
 
 def test_default_init_non_chat_target_behavior():
     config = PrependedConversationConfig()
-    assert config.non_chat_target_behavior == "normalize_first_turn"
+    assert config.non_chat_target_behavior is None
 
 
 def test_get_message_normalizer_returns_default_when_none():
@@ -37,14 +39,52 @@ def test_get_message_normalizer_returns_custom():
 
 
 def test_default_class_method():
-    config = PrependedConversationConfig.default()
+    with pytest.warns(DeprecationWarning, match="PrependedConversationConfig.default\\(\\) is deprecated"):
+        config = PrependedConversationConfig.default()
     assert config.apply_converters_to_roles == list(get_args(ChatMessageRole))
     assert config.message_normalizer is None
     assert config.non_chat_target_behavior == "raise"
 
 
+def test_explicit_raise_emits_deprecation_warning():
+    with pytest.warns(DeprecationWarning, match="non_chat_target_behavior"):
+        config = PrependedConversationConfig(non_chat_target_behavior="raise")
+    assert config.non_chat_target_behavior == "raise"
+
+
+def test_explicit_normalize_first_turn_emits_deprecation_warning():
+    with pytest.warns(DeprecationWarning, match="non_chat_target_behavior"):
+        config = PrependedConversationConfig(non_chat_target_behavior="normalize_first_turn")
+    assert config.non_chat_target_behavior == "normalize_first_turn"
+
+
+def test_default_init_does_not_emit_deprecation_warning(recwarn):
+    PrependedConversationConfig()
+    deprecation_warnings = [w for w in recwarn.list if issubclass(w.category, DeprecationWarning)]
+    assert deprecation_warnings == []
+
+
+def test_explicit_none_does_not_emit_deprecation_warning(recwarn):
+    PrependedConversationConfig(non_chat_target_behavior=None)
+    deprecation_warnings = [w for w in recwarn.list if issubclass(w.category, DeprecationWarning)]
+    assert deprecation_warnings == []
+
+
+def test_default_factory_emits_single_deprecation_warning(recwarn):
+    PrependedConversationConfig.default()
+    deprecation_warnings = [w for w in recwarn.list if issubclass(w.category, DeprecationWarning)]
+    assert len(deprecation_warnings) == 1
+
+
+def test_for_non_chat_target_emits_single_deprecation_warning(recwarn):
+    PrependedConversationConfig.for_non_chat_target()
+    deprecation_warnings = [w for w in recwarn.list if issubclass(w.category, DeprecationWarning)]
+    assert len(deprecation_warnings) == 1
+
+
 def test_for_non_chat_target_defaults():
-    config = PrependedConversationConfig.for_non_chat_target()
+    with pytest.warns(DeprecationWarning, match="PrependedConversationConfig.for_non_chat_target\\(\\) is deprecated"):
+        config = PrependedConversationConfig.for_non_chat_target()
     assert config.apply_converters_to_roles == list(get_args(ChatMessageRole))
     assert config.message_normalizer is None
     assert config.non_chat_target_behavior == "normalize_first_turn"
@@ -52,18 +92,21 @@ def test_for_non_chat_target_defaults():
 
 def test_for_non_chat_target_with_custom_normalizer():
     mock_normalizer = MagicMock()
-    config = PrependedConversationConfig.for_non_chat_target(message_normalizer=mock_normalizer)
+    with pytest.warns(DeprecationWarning, match="PrependedConversationConfig.for_non_chat_target\\(\\) is deprecated"):
+        config = PrependedConversationConfig.for_non_chat_target(message_normalizer=mock_normalizer)
     assert config.message_normalizer is mock_normalizer
     assert config.non_chat_target_behavior == "normalize_first_turn"
 
 
 def test_for_non_chat_target_with_specific_roles():
-    config = PrependedConversationConfig.for_non_chat_target(apply_converters_to_roles=["user"])
+    with pytest.warns(DeprecationWarning, match="PrependedConversationConfig.for_non_chat_target\\(\\) is deprecated"):
+        config = PrependedConversationConfig.for_non_chat_target(apply_converters_to_roles=["user"])
     assert config.apply_converters_to_roles == ["user"]
 
 
 def test_default_vs_init_differ_in_behavior():
-    default_config = PrependedConversationConfig.default()
+    with pytest.warns(DeprecationWarning):
+        default_config = PrependedConversationConfig.default()
     init_config = PrependedConversationConfig()
     assert default_config.non_chat_target_behavior == "raise"
-    assert init_config.non_chat_target_behavior == "normalize_first_turn"
+    assert init_config.non_chat_target_behavior is None