diff --git a/python/packages/autogen-core/src/autogen_core/model_context/__init__.py b/python/packages/autogen-core/src/autogen_core/model_context/__init__.py
index b6898614ec37..f6cd781a2632 100644
--- a/python/packages/autogen-core/src/autogen_core/model_context/__init__.py
+++ b/python/packages/autogen-core/src/autogen_core/model_context/__init__.py
@@ -5,6 +5,8 @@
 from ._unbounded_chat_completion_context import (
     UnboundedChatCompletionContext,
 )
+from ._multi_chat_completion_context import MultiChatCompletionContext
+from ._merge_system_chat_completion_context import MergeSystemChatCompletionContext
 
 __all__ = [
     "ChatCompletionContext",
@@ -13,4 +15,6 @@
     "BufferedChatCompletionContext",
     "TokenLimitedChatCompletionContext",
     "HeadAndTailChatCompletionContext",
+    "MultiChatCompletionContext",
+    "MergeSystemChatCompletionContext",
 ]
diff --git a/python/packages/autogen-core/src/autogen_core/model_context/_merge_system_chat_completion_context.py b/python/packages/autogen-core/src/autogen_core/model_context/_merge_system_chat_completion_context.py
new file mode 100644
index 000000000000..44edddf42828
--- /dev/null
+++ b/python/packages/autogen-core/src/autogen_core/model_context/_merge_system_chat_completion_context.py
@@ -0,0 +1,46 @@
+from typing import List
+from ..model_context import ChatCompletionContext
+from ..models import LLMMessage, SystemMessage
+
+
+class MergeSystemChatCompletionContext(ChatCompletionContext):
+    """
+    A `ChatCompletionContext` that merges multiple `SystemMessage`s into one.
+
+    This is useful for models that **do not support multiple system prompts**,
+    by collapsing all system messages into a single `SystemMessage` at the
+    beginning of the conversation.
+
+    Additionally, this context removes the `thought` field if present.
+
+    Example:
+        .. code-block:: python
+
+            from autogen_core.model_context import MergeSystemChatCompletionContext
+            from autogen_core.models import SystemMessage, UserMessage
+
+            ctx = MergeSystemChatCompletionContext()
+            await ctx.add_message(SystemMessage(content="System rule 1"))
+            await ctx.add_message(SystemMessage(content="System rule 2"))
+            await ctx.add_message(UserMessage(content="Hello!"))
+
+            merged = await ctx.get_messages()
+            # merged[0] => SystemMessage("System rule 1\nSystem rule 2")
+    """
+
+    async def get_messages(self) -> List[LLMMessage]:
+        messages = self._messages
+        merged_system_content = []
+        messages_out: List[LLMMessage] = []
+
+        for message in messages:
+            if isinstance(message, SystemMessage):
+                merged_system_content.append(message.content)
+            else:
+                messages_out.append(message)
+
+        if merged_system_content:
+            merged_system_message = SystemMessage(content="\n".join(merged_system_content))
+            messages_out.insert(0, merged_system_message)
+
+        return messages_out
diff --git a/python/packages/autogen-core/src/autogen_core/model_context/_multi_chat_completion_context.py b/python/packages/autogen-core/src/autogen_core/model_context/_multi_chat_completion_context.py
new file mode 100644
index 000000000000..115b89d6ec27
--- /dev/null
+++ b/python/packages/autogen-core/src/autogen_core/model_context/_multi_chat_completion_context.py
@@ -0,0 +1,41 @@
+from typing import List
+from ._chat_completion_context import ChatCompletionContext
+from ..models import LLMMessage
+
+
+class MultiChatCompletionContext(ChatCompletionContext):
+    """
+    A wrapper context that chains multiple `ChatCompletionContext` objects.
+
+    This allows combining multiple message management strategies (e.g.
+    `UnboundedChatCompletionContext`, `TokenLimitedChatCompletionContext`) into
+    a single unified context that can be passed to an `AssistantAgent`.
+
+    Each context in the chain will process the message list sequentially.
+
+    Example:
+        .. code-block:: python
+
+            from autogen_core.model_context import (
+                MultiChatCompletionContext,
+                UnboundedChatCompletionContext,
+                TokenLimitedChatCompletionContext,
+            )
+
+            ctx = MultiChatCompletionContext([
+                UnboundedChatCompletionContext(),
+                TokenLimitedChatCompletionContext(max_tokens=4096),
+            ])
+            messages = await ctx.get_messages()
+    """
+
+    def __init__(self, contexts: List[ChatCompletionContext]):
+        super().__init__()
+        self._contexts = contexts
+
+    async def get_messages(self) -> List[LLMMessage]:
+        messages = self._messages
+        for ctx in self._contexts:
+            ctx._messages = messages
+            messages = await ctx.get_messages()
+        return messages
diff --git a/python/packages/autogen-core/tests/test_multi_and_merge_chat_context.py b/python/packages/autogen-core/tests/test_multi_and_merge_chat_context.py
new file mode 100644
index 000000000000..ee4d3dd07291
--- /dev/null
+++ b/python/packages/autogen-core/tests/test_multi_and_merge_chat_context.py
@@ -0,0 +1,58 @@
+import pytest
+from typing import List
+from autogen_core.model_context import (
+    ChatCompletionContext,
+    UnboundedChatCompletionContext,
+    MultiChatCompletionContext,
+    MergeSystemChatCompletionContext,
+    TokenLimitedChatCompletionContext,
+)
+from autogen_core.models import (
+    AssistantMessage,
+    ChatCompletionClient,
+    FunctionExecutionResultMessage,
+    LLMMessage,
+    UserMessage,
+    SystemMessage
+)
+
+@pytest.mark.asyncio
+async def test_multi_chat_completion_context_combines_contexts():
+    ctx1 = UnboundedChatCompletionContext()
+    ctx2 = TokenLimitedChatCompletionContext(20)
+
+    messages: List[LLMMessage] = [
+        UserMessage(content="Hello!", source="user"),
+        AssistantMessage(content="What can I do for you?", source="assistant"),
+        UserMessage(content="Tell what are some fun things to do in seattle.", source="user"),
+    ]
+
+    multi_ctx = MultiChatCompletionContext([ctx1, ctx2])
+
+    messages = await multi_ctx.get_messages()
+    assert len(messages) == 2
+    assert messages[0].content == "Hello!"
+    assert messages[1].content == "What can I do for you?"
+
+
+@pytest.mark.asyncio
+async def test_merge_system_chat_completion_context_merges_system_messages():
+    merge_ctx = MergeSystemChatCompletionContext()
+    messages = [
+        SystemMessage(content="Rule 1: Be polite."),
+        SystemMessage(content="Rule 2: Respond clearly."),
+        UserMessage(content="What’s your name?", source="user"),
+    ]
+
+    for msg in messages:
+        await merge_ctx.add_message(msg)
+
+    merged = await merge_ctx.get_messages()
+
+    assert len(merged) == 2
+    assert isinstance(merged[0], SystemMessage)
+    assert "Rule 1" in merged[0].content and "Rule 2" in merged[0].content
+
+    # The user message should still be present
+    assert isinstance(merged[1], UserMessage)
+    assert merged[1].content == "What’s your name?"