diff --git a/.changeset/mcp-optional-rack.md b/.changeset/mcp-optional-rack.md
new file mode 100644
index 0000000..499a365
--- /dev/null
+++ b/.changeset/mcp-optional-rack.md
@@ -0,0 +1,5 @@
+---
+'posthog-ruby': patch
+---
+
+Fix `PostHog::MCP.instrument` raising `LoadError` at boot on stdio-only MCP servers that don't have the `rack` gem installed. A missing `rack` now only skips the Streamable HTTP transport extension.
diff --git a/lib/posthog/mcp.rb b/lib/posthog/mcp.rb
index d682966..cb0c533 100644
--- a/lib/posthog/mcp.rb
+++ b/lib/posthog/mcp.rb
@@ -84,7 +84,7 @@ def instrument(server, client = nil, options: nil, **kwargs)
           sink = resolved_client ? Sink.new(resolved_client) : nil
           data = TrackingData.new(options: opts, sink: sink, server_name: safe_call(server, :name),
                                   server_version: safe_call(server, :version))
-          install_extensions!
+          install_extensions!(opts)
           server.instance_variable_set(:@__posthog_mcp, data)
           register_missing_capability_tool(server, data)
           Analytics.new(server)
@@ -193,15 +193,23 @@ def register_missing_capability_tool(server, data)
         Log.warn(data.options, "Warning: could not register the #{name} tool - #{e.class}: #{e.message}")
       end
 
-      def install_extensions!
+      def install_extensions!(options)
         return if @extensions_installed
 
         ::MCP::Server.prepend(ServerExtension)
-        if defined?(::MCP::Server::Transports::StreamableHTTPTransport)
-          ::MCP::Server::Transports::StreamableHTTPTransport.prepend(TransportExtension)
-        end
+        install_transport_extension(options)
         @extensions_installed = true
       end
+
+      # The `mcp` gem autoloads its Streamable HTTP transport and that file raises
+      # LoadError without `rack`, which a stdio-only server legitimately lacks.
+      def install_transport_extension(options)
+        return unless defined?(::MCP::Server::Transports::StreamableHTTPTransport)
+
+        ::MCP::Server::Transports::StreamableHTTPTransport.prepend(TransportExtension)
+      rescue LoadError => e
+        Log.debug(options, "Skipping the Streamable HTTP transport extension - #{e.message}")
+      end
     end
   end
 end
diff --git a/spec/posthog/mcp/instrument_spec.rb b/spec/posthog/mcp/instrument_spec.rb
index 9598ecb..4b2f24a 100644
--- a/spec/posthog/mcp/instrument_spec.rb
+++ b/spec/posthog/mcp/instrument_spec.rb
@@ -3,6 +3,7 @@
 # rubocop:disable Layout/LineLength
 
 require_relative 'spec_helper'
+require 'open3'
 
 class PostHogMcpSpecEchoTool < MCP::Tool
   tool_name 'echo'
@@ -148,6 +149,37 @@ def initialize_request(id = 1, version = '2025-06-18')
       handle.capture('custom')
     end
 
+    it 'instruments a stdio-only server when the rack gem cannot be loaded' do
+      script = <<~RUBY
+        module Kernel
+          alias_method :require_without_rack_block, :require
+          def require(name)
+            raise LoadError, 'cannot load such file -- rack' if name == 'rack'
+
+            require_without_rack_block(name)
+          end
+        end
+        require 'posthog/mcp'
+        class EchoTool < MCP::Tool
+          tool_name 'echo'
+          input_schema(properties: { message: { type: 'string' } })
+          def self.call(message: nil, **) = MCP::Tool::Response.new([{ type: 'text', text: message }])
+        end
+        client = PostHog::Client.new(api_key: 'phc_test', test_mode: true)
+        server = MCP::Server.new(name: 'stdio', version: '1.0.0', tools: [EchoTool])
+        messages = []
+        handle = PostHog::MCP.instrument(server, client, logger: ->(m) { messages << m })
+        server.handle({ jsonrpc: '2.0', id: 1, method: 'tools/call', params: { name: 'echo', arguments: { message: 'hi' } } })
+        events = []
+        events << client.dequeue_last_message while client.queued_messages.positive?
+        puts [handle.class, events.map { |e| e[:event] }.include?('$mcp_tool_call'), messages.grep(/rack/).size].inspect
+      RUBY
+
+      stdout, stderr, status = Open3.capture3(RbConfig.ruby, '-Ilib', '-e', script)
+      expect(status.success?).to be(true), stderr
+      expect(stdout.lines.last).to eq("[PostHog::MCP::Analytics, true, 1]\n")
+    end
+
     it 'falls back to the posthog-rails facade client when present' do
       allow(Kernel).to receive(:warn)
       facade_client = PostHog::Client.new(api_key: 'phc_facade', test_mode: true)