diff --git a/requirements-constraints.txt b/requirements-constraints.txt
index 4fff18586..fc91739d7 100644
--- a/requirements-constraints.txt
+++ b/requirements-constraints.txt
@@ -99,7 +99,7 @@ chromadb==0.4.14
 google-cloud-storage==2.*
 google-cloud-aiplatform==1.*
 google-cloud-secret-manager==2.*
-anthropic[vertex]==0.34.2
+anthropic[vertex]==0.45.*
 langfuse @ git+https://github.com/jennmueng/langfuse-python.git@9d9350de1e4e84fa548fe84f82c1b826be17956e
 watchdog
 stumpy==1.13.0
diff --git a/requirements.txt b/requirements.txt
index f9e0fa6aa..115aab515 100644
--- a/requirements.txt
+++ b/requirements.txt
@@ -21,7 +21,7 @@ amqp==5.3.1
     # via kombu
 annotated-types==0.7.0
     # via pydantic
-anthropic==0.34.2
+anthropic==0.45.2
     # via -r requirements-constraints.txt
 anyio==4.8.0
     # via
@@ -729,7 +729,6 @@ threadpoolctl==3.2.0
     #   scikit-learn
 tokenizers==0.15.2
     # via
-    #   anthropic
     #   chromadb
     #   transformers
 torch==2.2.0
diff --git a/src/seer/automation/agent/client.py b/src/seer/automation/agent/client.py
index 0086b89d5..dbdebb295 100644
--- a/src/seer/automation/agent/client.py
+++ b/src/seer/automation/agent/client.py
@@ -437,7 +437,7 @@ def generate_text(
         max_tokens: int | None = None,
         timeout: float | None = None,
     ):
-        message_dicts, tool_dicts, system_prompt = self._prep_message_and_tools(
+        message_dicts, tool_dicts, system_prompt_block = self._prep_message_and_tools(
             messages=messages,
             prompt=prompt,
             system_prompt=system_prompt,
@@ -447,7 +447,7 @@ def generate_text(
         anthropic_client = self.get_client()
 
         completion = anthropic_client.messages.create(
-            system=system_prompt or NOT_GIVEN,
+            system=system_prompt_block or NOT_GIVEN,
             model=self.model_name,
             tools=cast(Iterable[ToolParam], tool_dicts) if tool_dicts else NOT_GIVEN,
             messages=cast(Iterable[MessageParam], message_dicts),
@@ -560,16 +560,24 @@ def _prep_message_and_tools(
         prompt: str | None = None,
         system_prompt: str | None = None,
         tools: list[FunctionTool] | None = None,
-    ) -> tuple[list[MessageParam], list[ToolParam] | None, str | None]:
+    ) -> tuple[list[MessageParam], list[ToolParam] | None, list[TextBlockParam] | None]:
         message_dicts = [cls.to_message_param(message) for message in messages] if messages else []
         if prompt:
             message_dicts.append(cls.to_message_param(Message(role="user", content=prompt)))
+        if message_dicts:
+            message_dicts[-1]["content"][0]["cache_control"] = {"type": "ephemeral"}  # type: ignore[index]
 
         tool_dicts = (
             [cls.to_tool_dict(tool) for tool in tools] if tools and len(tools) > 0 else None
         )
 
-        return message_dicts, tool_dicts, system_prompt
+        system_prompt_block = (
+            [TextBlockParam(type="text", text=system_prompt, cache_control={"type": "ephemeral"})]
+            if system_prompt
+            else None
+        )
+
+        return message_dicts, tool_dicts, system_prompt_block
 
     @observe(as_type="generation", name="Anthropic Stream")
     def generate_text_stream(
@@ -583,7 +591,7 @@ def generate_text_stream(
         max_tokens: int | None = None,
         timeout: float | None = None,
     ) -> Iterator[str | ToolCall | Usage]:
-        message_dicts, tool_dicts, system_prompt = self._prep_message_and_tools(
+        message_dicts, tool_dicts, system_prompt_block = self._prep_message_and_tools(
             messages=messages,
             prompt=prompt,
             system_prompt=system_prompt,
@@ -593,7 +601,7 @@ def generate_text_stream(
         anthropic_client = self.get_client()
 
         stream = anthropic_client.messages.create(
-            system=system_prompt or NOT_GIVEN,
+            system=system_prompt_block or NOT_GIVEN,
             model=self.model_name,
             tools=cast(Iterable[ToolParam], tool_dicts) if tool_dicts else NOT_GIVEN,
             messages=cast(Iterable[MessageParam], message_dicts),
diff --git a/tests/automation/agent/test_client.py b/tests/automation/agent/test_client.py
index d0fa6c690..5f5436e25 100644
--- a/tests/automation/agent/test_client.py
+++ b/tests/automation/agent/test_client.py
@@ -301,7 +301,7 @@ def test_anthropic_prep_message_and_tools():
         assert "description" in tool_dicts[0]
         assert "input_schema" in tool_dicts[0]
 
-    assert returned_system_prompt == system_prompt
+    assert returned_system_prompt[0]["text"] == system_prompt
 
 
 @pytest.mark.vcr()
diff --git a/tests/automation/autofix/_encrypted_cassettes/test_bad_request_is_not_retried[create_flaky_anthropic].yaml.encrypted b/tests/automation/autofix/_encrypted_cassettes/test_bad_request_is_not_retried[create_flaky_anthropic].yaml.encrypted
index 0c1b55cd1..6dfff2992 100644
Binary files a/tests/automation/autofix/_encrypted_cassettes/test_bad_request_is_not_retried[create_flaky_anthropic].yaml.encrypted and b/tests/automation/autofix/_encrypted_cassettes/test_bad_request_is_not_retried[create_flaky_anthropic].yaml.encrypted differ