diff --git a/src/pipecat/adapters/base_llm_adapter.py b/src/pipecat/adapters/base_llm_adapter.py
index 95082a5d6..0c8876553 100644
--- a/src/pipecat/adapters/base_llm_adapter.py
+++ b/src/pipecat/adapters/base_llm_adapter.py
@@ -129,4 +129,42 @@ class BaseLLMAdapter(ABC, Generic[TLLMInvocationParams]):
         # Fallback to return the same tools in case they are not in a standard format
         return tools
 
+    def _warn_about_orphaned_tool_messages(self, context: LLMContext) -> None:
+        """Warn if context contains messages referencing tools that aren't currently available.
+
+        This can happen when tools are removed/deactivated but the conversation history
+        still contains function calls or tool responses for those tools. Such orphaned
+        messages may cause API errors from the LLM provider.
+
+        Args:
+            context: The LLM context to check.
+        """
+        # Get the set of currently available tool names
+        available_tool_names: set[str] = set()
+        if isinstance(context.tools, ToolsSchema):
+            available_tool_names = {tool.name for tool in context.tools.standard_tools}
+            # Note: We don't check custom tools as they may have varying formats
+
+        # Track orphaned function names found in messages
+        orphaned_tools: set[str] = set()
+
+        for message in self.get_messages(context):
+            if isinstance(message, LLMSpecificMessage):
+                # Skip LLM-specific messages for now
+                continue
+
+            # Check for tool_calls in assistant messages
+            if message.get("tool_calls"):
+                for tc in message["tool_calls"]:
+                    func_name = tc.get("function", {}).get("name")
+                    if func_name and available_tool_names and func_name not in available_tool_names:
+                        orphaned_tools.add(func_name)
+
+        # Log warning for orphaned messages
+        if orphaned_tools:
+            logger.warning(
+                f"Context contains references to tools that are no longer available: "
+                f"{sorted(orphaned_tools)}. This may cause unexpected behavior or API errors."
+            )
+
     # TODO: we can move the logic to also handle the Messages here
diff --git a/src/pipecat/adapters/services/anthropic_adapter.py b/src/pipecat/adapters/services/anthropic_adapter.py
index ecc87154c..2a1762cf6 100644
--- a/src/pipecat/adapters/services/anthropic_adapter.py
+++ b/src/pipecat/adapters/services/anthropic_adapter.py
@@ -59,6 +59,9 @@ class AnthropicLLMAdapter(BaseLLMAdapter[AnthropicLLMInvocationParams]):
         Returns:
             Dictionary of parameters for invoking Anthropic's LLM API.
         """
+        # Warn about orphaned tool-related messages
+        self._warn_about_orphaned_tool_messages(context)
+
         messages = self._from_universal_context_messages(self.get_messages(context))
         return {
             "system": messages.system,
diff --git a/src/pipecat/adapters/services/aws_nova_sonic_adapter.py b/src/pipecat/adapters/services/aws_nova_sonic_adapter.py
index 1b62f5edc..b061956d1 100644
--- a/src/pipecat/adapters/services/aws_nova_sonic_adapter.py
+++ b/src/pipecat/adapters/services/aws_nova_sonic_adapter.py
@@ -83,6 +83,9 @@ class AWSNovaSonicLLMAdapter(BaseLLMAdapter[AWSNovaSonicLLMInvocationParams]):
         Returns:
             Dictionary of parameters for invoking AWS Nova Sonic's LLM API.
         """
+        # Warn about orphaned tool-related messages
+        self._warn_about_orphaned_tool_messages(context)
+
         messages = self._from_universal_context_messages(self.get_messages(context))
         return {
             "system_instruction": messages.system_instruction,
diff --git a/src/pipecat/adapters/services/bedrock_adapter.py b/src/pipecat/adapters/services/bedrock_adapter.py
index ccbbe5e2e..02d1cfc56 100644
--- a/src/pipecat/adapters/services/bedrock_adapter.py
+++ b/src/pipecat/adapters/services/bedrock_adapter.py
@@ -56,6 +56,9 @@ class AWSBedrockLLMAdapter(BaseLLMAdapter[AWSBedrockLLMInvocationParams]):
         Returns:
             Dictionary of parameters for invoking AWS Bedrock's LLM API.
         """
+        # Warn about orphaned tool-related messages
+        self._warn_about_orphaned_tool_messages(context)
+
         messages = self._from_universal_context_messages(self.get_messages(context))
         return {
             "system": messages.system,
diff --git a/src/pipecat/adapters/services/gemini_adapter.py b/src/pipecat/adapters/services/gemini_adapter.py
index 4968c2719..d4e1f4c22 100644
--- a/src/pipecat/adapters/services/gemini_adapter.py
+++ b/src/pipecat/adapters/services/gemini_adapter.py
@@ -62,6 +62,9 @@ class GeminiLLMAdapter(BaseLLMAdapter[GeminiLLMInvocationParams]):
         Returns:
             Dictionary of parameters for Gemini's API.
         """
+        # Warn about orphaned tool-related messages
+        self._warn_about_orphaned_tool_messages(context)
+
         messages = self._from_universal_context_messages(self.get_messages(context))
         return {
             "system_instruction": messages.system_instruction,
diff --git a/src/pipecat/adapters/services/grok_realtime_adapter.py b/src/pipecat/adapters/services/grok_realtime_adapter.py
index 03a3ed475..07b9f7157 100644
--- a/src/pipecat/adapters/services/grok_realtime_adapter.py
+++ b/src/pipecat/adapters/services/grok_realtime_adapter.py
@@ -59,6 +59,9 @@ class GrokRealtimeLLMAdapter(BaseLLMAdapter):
         Returns:
             Dictionary of parameters for invoking Grok's Voice Agent API.
         """
+        # Warn about orphaned tool-related messages
+        self._warn_about_orphaned_tool_messages(context)
+
         messages = self._from_universal_context_messages(self.get_messages(context))
         return {
             "system_instruction": messages.system_instruction,
diff --git a/src/pipecat/adapters/services/open_ai_adapter.py b/src/pipecat/adapters/services/open_ai_adapter.py
index f4b534f2c..ce2f398d5 100644
--- a/src/pipecat/adapters/services/open_ai_adapter.py
+++ b/src/pipecat/adapters/services/open_ai_adapter.py
@@ -60,6 +60,9 @@ class OpenAILLMAdapter(BaseLLMAdapter[OpenAILLMInvocationParams]):
         Returns:
             Dictionary of parameters for OpenAI's ChatCompletion API.
         """
+        # Warn about orphaned tool-related messages
+        self._warn_about_orphaned_tool_messages(context)
+
         return {
             "messages": self._from_universal_context_messages(self.get_messages(context)),
             # NOTE; LLMContext's tools are guaranteed to be a ToolsSchema (or NOT_GIVEN)
diff --git a/src/pipecat/adapters/services/open_ai_realtime_adapter.py b/src/pipecat/adapters/services/open_ai_realtime_adapter.py
index 136dc1a2f..0ecec76aa 100644
--- a/src/pipecat/adapters/services/open_ai_realtime_adapter.py
+++ b/src/pipecat/adapters/services/open_ai_realtime_adapter.py
@@ -54,6 +54,9 @@ class OpenAIRealtimeLLMAdapter(BaseLLMAdapter):
         Returns:
             Dictionary of parameters for invoking OpenAI Realtime's API.
         """
+        # Warn about orphaned tool-related messages
+        self._warn_about_orphaned_tool_messages(context)
+
         messages = self._from_universal_context_messages(self.get_messages(context))
         return {
             "system_instruction": messages.system_instruction,