diff --git a/lib/ruby_llm/chat.rb b/lib/ruby_llm/chat.rb
index afc572342..352dee9f6 100644
--- a/lib/ruby_llm/chat.rb
+++ b/lib/ruby_llm/chat.rb
@@ -32,20 +32,20 @@ def initialize(model: nil, provider: nil, assume_model_exists: false, context: n
       }
     end
 
-    def ask(message = nil, with: nil, &)
-      add_message role: :user, content: build_content(message, with)
+    def ask(message = nil, with: nil, cache_point: false, &)
+      add_message role: :user, content: build_content(message, with), cache_point: cache_point
       complete(&)
     end
 
     alias say ask
 
-    def with_instructions(instructions, append: false, replace: nil)
+    def with_instructions(instructions, append: false, replace: nil, cache_point: false)
       append ||= (replace == false) unless replace.nil?
 
       if append
-        append_system_instruction(instructions)
+        append_system_instruction(instructions, cache_point: cache_point)
       else
-        replace_system_instruction(instructions)
+        replace_system_instruction(instructions, cache_point: cache_point)
       end
 
       self
@@ -329,21 +329,16 @@ def content_like?(object)
       object.is_a?(Content) || object.is_a?(Content::Raw)
     end
 
-    def append_system_instruction(instructions)
+    def append_system_instruction(instructions, cache_point: false)
       system_messages, non_system_messages = @messages.partition { |msg| msg.role == :system }
-      system_messages << Message.new(role: :system, content: instructions)
+      system_messages << Message.new(role: :system, content: instructions, cache_point: cache_point)
       @messages = system_messages + non_system_messages
     end
 
-    def replace_system_instruction(instructions)
-      system_messages, non_system_messages = @messages.partition { |msg| msg.role == :system }
+    def replace_system_instruction(instructions, cache_point: false)
+      _, non_system_messages = @messages.partition { |msg| msg.role == :system }
 
-      if system_messages.empty?
-        system_messages = [Message.new(role: :system, content: instructions)]
-      else
-        system_messages.first.content = instructions
-        system_messages = [system_messages.first]
-      end
+      system_messages = [Message.new(role: :system, content: instructions, cache_point: cache_point)]
 
       @messages = system_messages + non_system_messages
     end
diff --git a/lib/ruby_llm/message.rb b/lib/ruby_llm/message.rb
index eefb93e55..dc88da741 100644
--- a/lib/ruby_llm/message.rb
+++ b/lib/ruby_llm/message.rb
@@ -5,7 +5,8 @@ module RubyLLM
   class Message
     ROLES = %i[system user assistant tool].freeze
 
-    attr_reader :role, :model_id, :tool_calls, :tool_call_id, :raw, :thinking, :tokens
+    attr_reader :role, :model_id, :tool_calls, :tool_call_id, :raw, :thinking, :tokens, :cache_point
+    alias cache_point? cache_point
     attr_writer :content
 
     def initialize(options = {})
@@ -24,6 +25,7 @@ def initialize(options = {})
       )
       @raw = options[:raw]
       @thinking = options[:thinking]
+      @cache_point = options.fetch(:cache_point, false)
 
       ensure_valid_role
     end
@@ -80,7 +82,8 @@ def to_h
         tool_calls: tool_calls,
         tool_call_id: tool_call_id,
         thinking: thinking&.text,
-        thinking_signature: thinking&.signature
+        thinking_signature: thinking&.signature,
+        cache_point: @cache_point || nil
       }.merge(tokens ? tokens.to_h : {}).compact
     end
 
diff --git a/lib/ruby_llm/provider.rb b/lib/ruby_llm/provider.rb
index a434ac114..db5e77447 100644
--- a/lib/ruby_llm/provider.rb
+++ b/lib/ruby_llm/provider.rb
@@ -257,7 +257,7 @@ def maybe_normalize_temperature(temperature, _model)
 
     def sync_response(connection, payload, additional_headers = {})
       response = connection.post completion_url, payload do |req|
-        req.headers = additional_headers.merge(req.headers) unless additional_headers.empty?
+        req.headers.merge!(additional_headers) unless additional_headers.empty?
       end
       parse_completion_response response
     end
diff --git a/lib/ruby_llm/providers/anthropic.rb b/lib/ruby_llm/providers/anthropic.rb
index a0686036f..f7e85ff32 100644
--- a/lib/ruby_llm/providers/anthropic.rb
+++ b/lib/ruby_llm/providers/anthropic.rb
@@ -22,6 +22,13 @@ def headers
         }
       end
 
+      def complete(messages, headers: {}, **kwargs, &block)
+        headers = headers.merge('anthropic-beta' => 'prompt-caching-2024-07-31') if messages.any?(&:cache_point?)
+
+        super(messages, headers: headers, **kwargs, &block) # rubocop:disable Style/SuperArguments
+        # Ignoring as we're modifying headers before calling super. We need to call super with modified headers.
+      end
+
       class << self
         def capabilities
           Anthropic::Capabilities
diff --git a/lib/ruby_llm/providers/anthropic/chat.rb b/lib/ruby_llm/providers/anthropic/chat.rb
index 9926fe98b..24f009a48 100644
--- a/lib/ruby_llm/providers/anthropic/chat.rb
+++ b/lib/ruby_llm/providers/anthropic/chat.rb
@@ -41,11 +41,13 @@ def build_system_content(system_messages)
           system_messages.flat_map do |msg|
             content = msg.content
 
-            if content.is_a?(RubyLLM::Content::Raw)
-              content.value
-            else
-              Media.format_content(content)
-            end
+            blocks = if content.is_a?(RubyLLM::Content::Raw)
+                       Array(content.value)
+                     else
+                       Array(Media.format_content(content))
+                     end
+
+            msg.cache_point? ? inject_cache_control(blocks) : blocks
           end
         end
 
@@ -159,6 +161,7 @@ def format_basic_message_with_thinking(msg, thinking_enabled)
           end
 
           append_formatted_content(content_blocks, msg.content)
+          inject_cache_control(content_blocks) if msg.cache_point?
 
           {
             role: convert_role(msg.role),
@@ -228,6 +231,17 @@ def append_formatted_content(content_blocks, content)
           end
         end
 
+        def inject_cache_control(blocks)
+          return blocks if blocks.empty?
+
+          last = blocks.last
+          # Don't duplicate if already present (e.g. Content::Raw with cache_control)
+          return blocks if last.is_a?(Hash) && last[:cache_control]
+
+          blocks[-1] = last.merge(cache_control: { type: 'ephemeral' })
+          blocks
+        end
+
         def convert_role(role)
           case role
           when :tool, :user then 'user'
diff --git a/lib/ruby_llm/providers/bedrock/chat.rb b/lib/ruby_llm/providers/bedrock/chat.rb
index c39fa2942..a2dbfa415 100644
--- a/lib/ruby_llm/providers/bedrock/chat.rb
+++ b/lib/ruby_llm/providers/bedrock/chat.rb
@@ -114,21 +114,26 @@ def render_message_content(msg)
           text_and_media_blocks = Media.render_content(msg.content, used_document_names: @used_document_names)
           blocks.concat(text_and_media_blocks) if text_and_media_blocks
 
-          if msg.tool_call?
-            msg.tool_calls.each_value do |tool_call|
-              blocks << {
-                toolUse: {
-                  toolUseId: tool_call.id,
-                  name: tool_call.name,
-                  input: tool_call.arguments
-                }
-              }
-            end
-          end
+          append_tool_use_blocks(blocks, msg)
+          blocks << { cachePoint: { type: 'default' } } if msg.cache_point?
 
           blocks
         end
 
+        def append_tool_use_blocks(blocks, msg)
+          return unless msg.tool_call?
+
+          msg.tool_calls.each_value do |tool_call|
+            blocks << {
+              toolUse: {
+                toolUseId: tool_call.id,
+                name: tool_call.name,
+                input: tool_call.arguments
+              }
+            }
+          end
+        end
+
         def render_raw_content(content)
           value = content.value
           value.is_a?(Array) ? value : [value]
@@ -200,7 +205,10 @@ def render_role(role)
         end
 
         def render_system(messages)
-          messages.flat_map { |msg| Media.render_content(msg.content, used_document_names: @used_document_names) }
+          messages.flat_map do |msg|
+            blocks = Media.render_content(msg.content, used_document_names: @used_document_names)
+            msg.cache_point? ? blocks + [{ cachePoint: { type: 'default' } }] : blocks
+          end
         end
 
         def render_inference_config(_model, temperature)
diff --git a/lib/ruby_llm/streaming.rb b/lib/ruby_llm/streaming.rb
index a671f9cca..df7e82566 100644
--- a/lib/ruby_llm/streaming.rb
+++ b/lib/ruby_llm/streaming.rb
@@ -9,7 +9,7 @@ def stream_response(connection, payload, additional_headers = {}, &block)
       accumulator = StreamAccumulator.new
 
       response = connection.post stream_url, payload do |req|
-        req.headers = additional_headers.merge(req.headers) unless additional_headers.empty?
+        req.headers.merge!(additional_headers) unless additional_headers.empty?
         if faraday_1?
           req.options[:on_data] = handle_stream do |chunk|
             accumulator.add chunk
diff --git a/spec/ruby_llm/chat_cache_point_spec.rb b/spec/ruby_llm/chat_cache_point_spec.rb
new file mode 100644
index 000000000..2f730c1a4
--- /dev/null
+++ b/spec/ruby_llm/chat_cache_point_spec.rb
@@ -0,0 +1,58 @@
+# frozen_string_literal: true
+
+require 'spec_helper'
+
+RSpec.describe RubyLLM::Chat do
+  include_context 'with configured RubyLLM'
+
+  describe 'cache_point forwarding' do
+    let(:chat) { RubyLLM.chat }
+
+    shared_examples 'a method that supports cache_point' do |message_finder|
+      it 'sets cache_point? true when cache_point: true' do
+        action.call(cache_point: true)
+        message = message_finder.call(chat)
+        expect(message).not_to be_nil
+        expect(message.cache_point?).to be true
+      end
+
+      it 'sets cache_point? false when cache_point is omitted' do
+        action.call
+        message = message_finder.call(chat)
+        expect(message).not_to be_nil
+        expect(message.cache_point?).to be false
+      end
+    end
+
+    describe '#with_instructions' do
+      let(:action) { ->(opts = {}) { chat.with_instructions('Be helpful', **opts) } }
+      let(:finder) { ->(c) { c.messages.find { |m| m.role == :system } } }
+
+      it_behaves_like 'a method that supports cache_point', ->(c) { c.messages.find { |m| m.role == :system } }
+
+      it 'sets cache_point? true on appended message only' do
+        chat.with_instructions('First instruction')
+        chat.with_instructions('Second instruction', append: true, cache_point: true)
+        system_msgs = chat.messages.select { |m| m.role == :system }
+        expect(system_msgs.last.cache_point?).to be true
+        expect(system_msgs.first.cache_point?).to be false
+      end
+
+      it 'preserves cache_point: true when replacing' do
+        chat.with_instructions('Old instruction', cache_point: false)
+        chat.with_instructions('New instruction', replace: true, cache_point: true)
+        system_msgs = chat.messages.select { |m| m.role == :system }
+        expect(system_msgs.size).to eq(1)
+        expect(system_msgs.first.cache_point?).to be true
+      end
+    end
+
+    describe '#ask' do
+      before { allow(chat).to receive(:complete) }
+
+      let(:action) { ->(opts = {}) { chat.ask('Hello', **opts) } }
+
+      it_behaves_like 'a method that supports cache_point', ->(c) { c.messages.find { |m| m.role == :user } }
+    end
+  end
+end
diff --git a/spec/ruby_llm/message_spec.rb b/spec/ruby_llm/message_spec.rb
index a787fd0e7..2672f911f 100644
--- a/spec/ruby_llm/message_spec.rb
+++ b/spec/ruby_llm/message_spec.rb
@@ -3,6 +3,30 @@
 require 'spec_helper'
 
 RSpec.describe RubyLLM::Message do
+  describe '#cache_point?' do
+    it 'returns false by default' do
+      message = described_class.new(role: :user, content: 'hello')
+      expect(message.cache_point?).to be false
+    end
+
+    it 'returns true when constructed with cache_point: true' do
+      message = described_class.new(role: :user, content: 'hello', cache_point: true)
+      expect(message.cache_point?).to be true
+    end
+  end
+
+  describe '#to_h' do
+    it 'omits cache_point key when false' do
+      message = described_class.new(role: :user, content: 'hello')
+      expect(message.to_h).not_to have_key(:cache_point)
+    end
+
+    it 'includes cache_point: true when set' do
+      message = described_class.new(role: :user, content: 'hello', cache_point: true)
+      expect(message.to_h[:cache_point]).to be true
+    end
+  end
+
   describe '#content' do
     it 'normalizes nil content to empty string for assistant tool-call messages' do
       tool_call = RubyLLM::ToolCall.new(id: 'call_1', name: 'weather', arguments: {})
diff --git a/spec/ruby_llm/providers/anthropic/chat_cache_control_spec.rb b/spec/ruby_llm/providers/anthropic/chat_cache_control_spec.rb
new file mode 100644
index 000000000..1fa15c8f5
--- /dev/null
+++ b/spec/ruby_llm/providers/anthropic/chat_cache_control_spec.rb
@@ -0,0 +1,70 @@
+# frozen_string_literal: true
+
+require 'spec_helper'
+
+RSpec.describe RubyLLM::Providers::Anthropic::Chat do
+  let(:model) { instance_double(RubyLLM::Model::Info, id: 'claude-sonnet-4-5', max_tokens: nil) }
+
+  def render(messages)
+    described_class.render_payload(
+      messages,
+      tools: {},
+      temperature: nil,
+      model: model,
+      stream: false,
+      schema: nil
+    )
+  end
+
+  describe 'cache_control injection' do
+    context 'with a system message where cache_point is true' do
+      it 'adds cache_control to the last system block' do
+        msg = RubyLLM::Message.new(role: :system, content: 'You are helpful.', cache_point: true)
+        payload = render([msg, RubyLLM::Message.new(role: :user, content: 'Hi')])
+
+        last_block = payload[:system].last
+        expect(last_block[:cache_control]).to eq(type: 'ephemeral')
+      end
+
+      it 'does not add cache_control when cache_point is false' do
+        msg = RubyLLM::Message.new(role: :system, content: 'You are helpful.')
+        payload = render([msg, RubyLLM::Message.new(role: :user, content: 'Hi')])
+
+        payload[:system].each do |block|
+          expect(block).not_to have_key(:cache_control)
+        end
+      end
+    end
+
+    context 'with a user message where cache_point is true' do
+      it 'adds cache_control to the last content block' do
+        msg = RubyLLM::Message.new(role: :user, content: 'Tell me a story.', cache_point: true)
+        payload = render([msg])
+
+        last_block = payload[:messages].first[:content].last
+        expect(last_block[:cache_control]).to eq(type: 'ephemeral')
+      end
+
+      it 'does not add cache_control when cache_point is false' do
+        msg = RubyLLM::Message.new(role: :user, content: 'Tell me a story.')
+        payload = render([msg])
+
+        payload[:messages].first[:content].each do |block|
+          expect(block).not_to have_key(:cache_control)
+        end
+      end
+    end
+
+    context 'when a Content::Raw block already contains cache_control' do
+      it 'does not duplicate when cache_control' do
+        raw = RubyLLM::Providers::Anthropic::Content.new('Cached system', cache: true)
+        msg = RubyLLM::Message.new(role: :system, content: raw, cache_point: true)
+        payload = render([msg, RubyLLM::Message.new(role: :user, content: 'Hi')])
+
+        blocks_with_cache = payload[:system].select { |b| b[:cache_control] }
+        expect(blocks_with_cache.length).to eq(1)
+        expect(blocks_with_cache.first[:cache_control]).to eq(type: 'ephemeral')
+      end
+    end
+  end
+end
diff --git a/spec/ruby_llm/providers/bedrock/chat_cache_point_spec.rb b/spec/ruby_llm/providers/bedrock/chat_cache_point_spec.rb
new file mode 100644
index 000000000..7f562657f
--- /dev/null
+++ b/spec/ruby_llm/providers/bedrock/chat_cache_point_spec.rb
@@ -0,0 +1,77 @@
+# frozen_string_literal: true
+
+require 'spec_helper'
+
+RSpec.describe RubyLLM::Providers::Bedrock::Chat do
+  let(:model) do
+    instance_double(RubyLLM::Model::Info,
+                    id: 'anthropic.claude-haiku-4-5-20251001-v1:0',
+                    max_tokens: nil,
+                    metadata: {})
+  end
+
+  let(:base_args) do
+    { tools: {}, temperature: nil, model: model, stream: false }
+  end
+
+  def render(messages)
+    described_class.render_payload(messages, **base_args)
+  end
+
+  def msg(role, content, cache_point: false)
+    RubyLLM::Message.new(role: role, content: content, cache_point: cache_point)
+  end
+
+  describe 'cache_point injection' do
+    context 'with a system message where cache_point is true' do
+      it 'appends a cachePoint block to the system content' do
+        payload = render([msg(:system, 'You are helpful.', cache_point: true),
+                          msg(:user, 'Hi')])
+
+        last_block = payload[:system].last
+        expect(last_block).to eq(cachePoint: { type: 'default' })
+      end
+
+      it 'does not append cachePoint when cache_point is false' do
+        payload = render([msg(:system, 'You are helpful.'), msg(:user, 'Hi')])
+
+        expect(payload[:system]).not_to include(cachePoint: { type: 'default' })
+      end
+    end
+
+    context 'with a user message where cache_point is true' do
+      it 'appends a cachePoint block to the message content' do
+        payload = render([msg(:user, 'Tell me a story.', cache_point: true)])
+
+        last_block = payload[:messages].first[:content].last
+        expect(last_block).to eq(cachePoint: { type: 'default' })
+      end
+
+      it 'does not append cachePoint when cache_point is false' do
+        payload = render([msg(:user, 'Tell me a story.')])
+
+        content = payload[:messages].first[:content]
+        expect(content).not_to include(cachePoint: { type: 'default' })
+      end
+    end
+
+    context 'when multiple messages have cache_point: true' do
+      it 'appends cachePoint to each cache-pointed message' do
+        payload = render([
+                           msg(:system, 'System prompt', cache_point: true),
+                           msg(:user, 'User context', cache_point: true),
+                           msg(:user, 'Dynamic question')
+                         ])
+
+        system_has_cache = payload[:system].last == { cachePoint: { type: 'default' } }
+        user_messages = payload[:messages]
+        first_user_has_cache = user_messages.first[:content].last == { cachePoint: { type: 'default' } }
+        last_user_no_cache = user_messages.last[:content].last != { cachePoint: { type: 'default' } }
+
+        expect(system_has_cache).to be true
+        expect(first_user_has_cache).to be true
+        expect(last_user_no_cache).to be true
+      end
+    end
+  end
+end