diff --git a/lib/model_context_protocol/server/tool.rb b/lib/model_context_protocol/server/tool.rb
index 31b16fc..3c1fabd 100644
--- a/lib/model_context_protocol/server/tool.rb
+++ b/lib/model_context_protocol/server/tool.rb
@@ -94,7 +94,7 @@ def define(&block)
         @title = definition_dsl.title
         @input_schema = definition_dsl.input_schema
         @output_schema = definition_dsl.output_schema
-        @annotations = definition_dsl.annotations
+        @annotations = definition_dsl.defined_annotations
         @security_schemes = definition_dsl.security_schemes
       end
 
@@ -104,7 +104,7 @@ def inherited(subclass)
         subclass.instance_variable_set(:@title, @title)
         subclass.instance_variable_set(:@input_schema, @input_schema)
         subclass.instance_variable_set(:@output_schema, @output_schema)
-        subclass.instance_variable_set(:@annotations, @annotations)
+        subclass.instance_variable_set(:@annotations, @annotations&.dup)
         subclass.instance_variable_set(:@security_schemes, @security_schemes)
       end
 
@@ -124,7 +124,8 @@ def definition
         result = {name: @name, description: @description, inputSchema: @input_schema}
         result[:title] = @title if @title
         result[:outputSchema] = @output_schema if @output_schema
-        result[:annotations] = @annotations if @annotations
+        annotations_hash = @annotations&.serialized
+        result[:annotations] = annotations_hash if annotations_hash
         result[:securitySchemes] = @security_schemes if @security_schemes
         result
       end
@@ -156,9 +157,12 @@ def output_schema(&block)
         @output_schema
       end
 
+      attr_reader :defined_annotations
+
       def annotations(&block)
-        @annotations = instance_eval(&block) if block_given?
-        @annotations
+        @defined_annotations = AnnotationsDSL.new
+        @defined_annotations.instance_eval(&block)
+        @defined_annotations
       end
 
       def security_schemes(&block)
@@ -166,5 +170,51 @@ def security_schemes(&block)
         @security_schemes
       end
     end
+
+    class AnnotationsDSL
+      def initialize
+        @read_only_hint = nil
+        @destructive_hint = nil
+        @idempotent_hint = nil
+        @open_world_hint = nil
+      end
+
+      def read_only_hint(value)
+        validate_boolean!(:read_only_hint, value)
+        @read_only_hint = value
+      end
+
+      def destructive_hint(value)
+        validate_boolean!(:destructive_hint, value)
+        @destructive_hint = value
+      end
+
+      def idempotent_hint(value)
+        validate_boolean!(:idempotent_hint, value)
+        @idempotent_hint = value
+      end
+
+      def open_world_hint(value)
+        validate_boolean!(:open_world_hint, value)
+        @open_world_hint = value
+      end
+
+      def serialized
+        result = {}
+        result[:readOnlyHint] = @read_only_hint unless @read_only_hint.nil?
+        result[:destructiveHint] = @destructive_hint unless @destructive_hint.nil?
+        result[:idempotentHint] = @idempotent_hint unless @idempotent_hint.nil?
+        result[:openWorldHint] = @open_world_hint unless @open_world_hint.nil?
+        result.empty? ? nil : result
+      end
+
+      private
+
+      def validate_boolean!(field, value)
+        unless value.is_a?(TrueClass) || value.is_a?(FalseClass)
+          raise ArgumentError, "#{field} must be a boolean, got: #{value.inspect}"
+        end
+      end
+    end
   end
 end
diff --git a/spec/lib/model_context_protocol/server/tool_spec.rb b/spec/lib/model_context_protocol/server/tool_spec.rb
index 0405188..e874cd9 100644
--- a/spec/lib/model_context_protocol/server/tool_spec.rb
+++ b/spec/lib/model_context_protocol/server/tool_spec.rb
@@ -314,12 +314,12 @@
             }
           end
           annotations do
-            {readOnlyHint: true}
+            read_only_hint true
           end
         end
       end
 
-      expect(tool_with_annotations.annotations).to eq(readOnlyHint: true)
+      expect(tool_with_annotations.annotations.serialized).to eq(readOnlyHint: true)
     end
 
     it "inherits annotations in subclasses" do
@@ -328,12 +328,14 @@
           name "fetch"
           description "Fetch the full contents of a single resource"
           input_schema { {type: "object", properties: {}, required: []} }
-          annotations { {readOnlyHint: true} }
+          annotations do
+            read_only_hint true
+          end
         end
       end
 
       child_tool = Class.new(parent_tool)
-      expect(child_tool.annotations).to eq({readOnlyHint: true})
+      expect(child_tool.annotations.serialized).to eq({readOnlyHint: true})
     end
 
     it "sets security schemes when provided" do
@@ -456,7 +458,7 @@
             }
           end
           annotations do
-            {readOnlyHint: true}
+            read_only_hint true
           end
         end
       end
@@ -558,6 +560,120 @@ def call
     end
   end
 
+  describe "AnnotationsDSL" do
+    it "serializes all hints with camelCase keys" do
+      tool = Class.new(ModelContextProtocol::Server::Tool) do
+        define do
+          name "test"
+          description "Test tool"
+          input_schema { {type: "object", properties: {}, required: []} }
+          annotations do
+            read_only_hint false
+            destructive_hint true
+            idempotent_hint false
+            open_world_hint true
+          end
+        end
+      end
+
+      expect(tool.annotations.serialized).to eq(
+        readOnlyHint: false,
+        destructiveHint: true,
+        idempotentHint: false,
+        openWorldHint: true
+      )
+    end
+
+    it "only serializes hints that are set" do
+      tool = Class.new(ModelContextProtocol::Server::Tool) do
+        define do
+          name "test"
+          description "Test tool"
+          input_schema { {type: "object", properties: {}, required: []} }
+          annotations do
+            destructive_hint false
+          end
+        end
+      end
+
+      expect(tool.annotations.serialized).to eq(destructiveHint: false)
+    end
+
+    it "returns nil from serialized when no hints are set" do
+      tool = Class.new(ModelContextProtocol::Server::Tool) do
+        define do
+          name "test"
+          description "Test tool"
+          input_schema { {type: "object", properties: {}, required: []} }
+          annotations do
+          end
+        end
+      end
+
+      expect(tool.annotations.serialized).to be_nil
+    end
+
+    it "raises ArgumentError for non-boolean read_only_hint" do
+      expect {
+        Class.new(ModelContextProtocol::Server::Tool) do
+          define do
+            name "test"
+            description "Test tool"
+            input_schema { {type: "object", properties: {}, required: []} }
+            annotations do
+              read_only_hint "true"
+            end
+          end
+        end
+      }.to raise_error(ArgumentError, /read_only_hint must be a boolean/)
+    end
+
+    it "raises ArgumentError for non-boolean destructive_hint" do
+      expect {
+        Class.new(ModelContextProtocol::Server::Tool) do
+          define do
+            name "test"
+            description "Test tool"
+            input_schema { {type: "object", properties: {}, required: []} }
+            annotations do
+              destructive_hint 1
+            end
+          end
+        end
+      }.to raise_error(ArgumentError, /destructive_hint must be a boolean/)
+    end
+
+    it "raises ArgumentError for non-boolean idempotent_hint" do
+      expect {
+        Class.new(ModelContextProtocol::Server::Tool) do
+          define do
+            name "test"
+            description "Test tool"
+            input_schema { {type: "object", properties: {}, required: []} }
+            annotations do
+              idempotent_hint nil
+            end
+          end
+        end
+      }.to raise_error(ArgumentError, /idempotent_hint must be a boolean/)
+    end
+
+    it "raises ArgumentError for non-boolean open_world_hint" do
+      expect {
+        Class.new(ModelContextProtocol::Server::Tool) do
+          define do
+            name "test"
+            description "Test tool"
+            input_schema { {type: "object", properties: {}, required: []} }
+            annotations do
+              open_world_hint "false"
+            end
+          end
+        end
+      }.to raise_error(ArgumentError, /open_world_hint must be a boolean/)
+    end
+  end
+
   describe "server logger integration" do
     it "calls server_logger during execution" do
       allow(client_logger).to receive(:info)
diff --git a/spec/support/tools/test_tool_with_annotations.rb b/spec/support/tools/test_tool_with_annotations.rb
index 67e793d..45e8244 100644
--- a/spec/support/tools/test_tool_with_annotations.rb
+++ b/spec/support/tools/test_tool_with_annotations.rb
@@ -15,7 +15,7 @@ class TestToolWithAnnotations < ModelContextProtocol::Server::Tool
       }
     end
     annotations do
-      {readOnlyHint: true}
+      read_only_hint true
     end
   end