diff --git a/lib/mcp/server.rb b/lib/mcp/server.rb
index 0f77af3c..586d0def 100644
--- a/lib/mcp/server.rb
+++ b/lib/mcp/server.rb
@@ -745,11 +745,15 @@ def call_tool(request, session: nil, related_request_id: nil, cancellation: nil)
 
       progress_token = request.dig(:_meta, :progressToken)
 
-      result = call_tool_with_args(
+      response = call_tool_with_args(
         tool, arguments, server_context_with_meta(request), progress_token: progress_token, session: session, related_request_id: related_request_id, cancellation: cancellation
       )
+      result = response.to_h
       validate_tool_call_result!(tool, result)
-      serialize_structured_content_fallback(result)
+      serialize_structured_content_fallback(
+        result,
+        content_provided: response.respond_to?(:content_provided?) && response.content_provided?,
+      )
     rescue RequestHandlerError, CancelledError
       # CancelledError is intentionally not wrapped so `handle_request` can turn it into
       # `JsonRpcHandler::NO_RESPONSE` per the MCP cancellation spec.
@@ -986,14 +990,18 @@ def validate_tool_call_result!(tool, result)
 
     # Per SEP-2106, `structuredContent` may be any JSON value, not only an object.
     # Clients on older protocol versions may only read `content`,
-    # so when a tool returns non-object structured content without providing
-    # any content blocks, mirror the value into `content` as serialized JSON text.
-    def serialize_structured_content_fallback(result)
+    # so when a tool returns non-object structured content without explicitly
+    # providing `content`, mirror the value into serialized JSON text.
+    def serialize_structured_content_fallback(result, content_provided: false)
       structured = result[:structuredContent]
       return result if structured.nil? || structured.is_a?(Hash)
+      return result if content_provided
       return result unless result[:content].nil? || result[:content].empty?
 
-      result.merge(content: [{ type: "text", text: JSON.generate(structured) }])
+      serialized = JSON.generate(structured)
+      return result if JSON.parse(serialized).is_a?(Hash)
+
+      result.merge(content: [{ type: "text", text: serialized }])
     end
 
     # Whether a tool/prompt handler opts in to receiving an `MCP::ServerContext`.
@@ -1026,9 +1034,9 @@ def call_tool_with_args(tool, arguments, context, progress_token: nil, session:
           related_request_id: related_request_id,
           cancellation: cancellation,
         )
-        tool.call(**args, server_context: server_context).to_h
+        tool.call(**args, server_context: server_context)
       else
-        tool.call(**args).to_h
+        tool.call(**args)
       end
     end
 
diff --git a/lib/mcp/tool/response.rb b/lib/mcp/tool/response.rb
index 2532ea83..9e4b2ecd 100644
--- a/lib/mcp/tool/response.rb
+++ b/lib/mcp/tool/response.rb
@@ -7,18 +7,24 @@ class Response
 
       attr_reader :content, :structured_content, :meta
 
-      def initialize(content = nil, deprecated_error = NOT_GIVEN, error: false, structured_content: nil, meta: nil)
+      def initialize(content = NOT_GIVEN, deprecated_error = NOT_GIVEN, error: false, structured_content: nil, meta: nil)
         if deprecated_error != NOT_GIVEN
           warn("Passing `error` with the 2nd argument of `Response.new` is deprecated. Use keyword argument like `Response.new(content, error: error)` instead.", uplevel: 1)
           error = deprecated_error
         end
 
-        @content = content || []
+        content_given = !content.equal?(NOT_GIVEN)
+        @content_provided = content_given && !content.nil?
+        @content = content_given ? (content || []) : []
         @error = error
         @structured_content = structured_content
         @meta = meta
       end
 
+      def content_provided?
+        @content_provided
+      end
+
       def error?
         !!@error
       end
diff --git a/test/mcp/server_test.rb b/test/mcp/server_test.rb
index 18240b0e..7281a434 100644
--- a/test/mcp/server_test.rb
+++ b/test/mcp/server_test.rb
@@ -3156,6 +3156,16 @@ def call(numbers:, strings:, objects:, server_context: nil)
       end
     end
 
+    class JsonObjectValue
+      def initialize(value)
+        @value = value
+      end
+
+      def to_json(*args)
+        @value.to_json(*args)
+      end
+    end
+
     test "server_context_with_meta uses accessor method, not ivar directly" do
       subclass = Class.new(Server) do
         def server_context
@@ -3247,23 +3257,28 @@ def server_context
       end
     end
 
-    test "#handle tools/call mirrors non-object structuredContent into serialized text content" do
+    test "#handle tools/call mirrors non-object structuredContent when content is omitted or nil" do
       # Per SEP-2106, `structuredContent` may be any JSON value. Older clients may only read `content`,
       # so the server adds a serialized fallback when the tool provided no content blocks.
       server = Server.new(name: "structured_test", tools: [])
-      server.define_tool(name: "array_tool") do
+      server.define_tool(name: "nil_content_tool") do
         Tool::Response.new(nil, structured_content: [1, 2])
       end
+      server.define_tool(name: "omitted_content_tool") do
+        Tool::Response.new(structured_content: [1, 2])
+      end
 
-      response = server.handle({
-        jsonrpc: "2.0",
-        method: "tools/call",
-        id: 1,
-        params: { name: "array_tool", arguments: {} },
-      })
+      ["nil_content_tool", "omitted_content_tool"].each_with_index do |tool_name, index|
+        response = server.handle({
+          jsonrpc: "2.0",
+          method: "tools/call",
+          id: index + 1,
+          params: { name: tool_name, arguments: {} },
+        })
 
-      assert_equal [1, 2], response.dig(:result, :structuredContent)
-      assert_equal [{ type: "text", text: "[1,2]" }], response.dig(:result, :content)
+        assert_equal [1, 2], response.dig(:result, :structuredContent)
+        assert_equal [{ type: "text", text: "[1,2]" }], response.dig(:result, :content)
+      end
     end
 
     test "#handle tools/call does not overwrite explicit content when structuredContent is non-object" do
@@ -3299,6 +3314,60 @@ def server_context
       assert_empty response.dig(:result, :content)
     end
 
+    test "#handle tools/call recognizes object-like structuredContent by its JSON shape" do
+      structured_content = JsonObjectValue.new(answer: 42)
+      server = Server.new(name: "structured_test", tools: [])
+      server.define_tool(name: "object_tool") do
+        Tool::Response.new(nil, structured_content: structured_content)
+      end
+
+      response = server.handle({
+        jsonrpc: "2.0",
+        method: "tools/call",
+        id: 1,
+        params: { name: "object_tool", arguments: {} },
+      })
+
+      assert_equal structured_content, response.dig(:result, :structuredContent)
+      assert_empty response.dig(:result, :content)
+    end
+
+    test "#handle tools/call preserves explicit empty content for non-object structuredContent" do
+      server = Server.new(name: "structured_test", tools: [])
+      server.define_tool(name: "array_tool") do
+        Tool::Response.new([], structured_content: [1, 2])
+      end
+
+      response = server.handle({
+        jsonrpc: "2.0",
+        method: "tools/call",
+        id: 1,
+        params: { name: "array_tool", arguments: {} },
+      })
+
+      assert_equal [1, 2], response.dig(:result, :structuredContent)
+      assert_empty response.dig(:result, :content)
+    end
+
+    test "#handle tools/call preserves explicit empty content for object-like structuredContent" do
+      structured_content = JsonObjectValue.new(answer: 42)
+
+      server = Server.new(name: "structured_test", tools: [])
+      server.define_tool(name: "object_tool") do
+        Tool::Response.new([], structured_content: structured_content)
+      end
+
+      response = server.handle({
+        jsonrpc: "2.0",
+        method: "tools/call",
+        id: 1,
+        params: { name: "object_tool", arguments: {} },
+      })
+
+      assert_equal structured_content, response.dig(:result, :structuredContent)
+      assert_empty response.dig(:result, :content)
+    end
+
     test "list results carry ttlMs and cacheScope when ttl_ms is configured" do
       # SEP-2549 cache hints. The cacheScope default is "public", matching
       # the spec default and the Python SDK.
diff --git a/test/mcp/tool/response_test.rb b/test/mcp/tool/response_test.rb
index 122dbb07..afa7d3b5 100644
--- a/test/mcp/tool/response_test.rb
+++ b/test/mcp/tool/response_test.rb
@@ -16,6 +16,12 @@ class ResponseTest < ActiveSupport::TestCase
         refute response.error?
       end
 
+      test "#content_provided? distinguishes empty content from omitted or nil content" do
+        assert Response.new([]).content_provided?
+        refute Response.new.content_provided?
+        refute Response.new(nil).content_provided?
+      end
+
       test "#initialize with content and error set to true" do
         content = [{
           type: "text",