@@ -167,3 +167,74 @@ export function wrapAllMCPHandlers(serverInstance: MCPServerInstance): void {
   wrapResourceHandlers(serverInstance);
   wrapPromptHandlers(serverInstance);
 }
+
+/**
+ * Retroactively wraps handlers on tools, resources, and prompts that were registered
+ * before `wrapMcpServerWithSentry` was called.
+ *
+ * The MCP SDK stores registered entries in private maps and invokes them via the entry's
+ * own property at call time — `executor` for tools, `readCallback` for resources, and
+ * `handler` for prompts. Replacing those properties
+ * in-place is therefore equivalent to having wrapped the original registration call.
+ *
+ * NOTE: This intentionally accesses private MCP SDK internals (`_registeredTools` etc.).
+ * The properties and their shapes are verified against @modelcontextprotocol/sdk source:
+ * https://github.com/modelcontextprotocol/typescript-sdk/blob/2c0c481cb9dbfd15c8613f765c940a5f5bace94d/packages/server/src/server/mcp.ts#L304
+ * When upgrading the MCP SDK, re-verify that these internal maps and their callable
+ * properties still exist and are invoked directly (not captured by closure at registration).
+ * All access is defensive — if a property is absent or not a function we skip silently.
+ * @internal
+ */
+export function wrapExistingHandlers(serverInstance: MCPServerInstance): void {
+  const server = serverInstance as unknown as Record<string, unknown>;
+
+  // Tools: MCP SDK calls registeredTool.executor (generated from handler at registration time)
+  const registeredTools = server['_registeredTools'];
+  if (registeredTools && typeof registeredTools === 'object') {
+    for (const [name, tool] of Object.entries(registeredTools as Record<string, Record<string, unknown>>)) {
+      if (typeof tool['executor'] === 'function') {
+        tool['executor'] = createWrappedHandler(tool['executor'] as MCPHandler, 'registerTool', name);
+      }
+    }
+  }
+
+  // Resources: MCP SDK calls registeredResource.readCallback
+  const registeredResources = server['_registeredResources'];
+  if (registeredResources && typeof registeredResources === 'object') {
+    for (const [name, resource] of Object.entries(registeredResources as Record<string, Record<string, unknown>>)) {
+      if (typeof resource['readCallback'] === 'function') {
+        resource['readCallback'] = createWrappedHandler(
+          resource['readCallback'] as MCPHandler,
+          'registerResource',
+          name,
+        );
+      }
+    }
+  }
+
+  // Resource templates: MCP SDK calls registeredResourceTemplate.readCallback
+  const registeredResourceTemplates = server['_registeredResourceTemplates'];
+  if (registeredResourceTemplates && typeof registeredResourceTemplates === 'object') {
+    for (const [name, template] of Object.entries(
+      registeredResourceTemplates as Record<string, Record<string, unknown>>,
+    )) {
+      if (typeof template['readCallback'] === 'function') {
+        template['readCallback'] = createWrappedHandler(
+          template['readCallback'] as MCPHandler,
+          'registerResource',
+          name,
+        );
+      }
+    }
+  }
+
+  // Prompts: MCP SDK calls registeredPrompt.handler
+  const registeredPrompts = server['_registeredPrompts'];
+  if (registeredPrompts && typeof registeredPrompts === 'object') {
+    for (const [name, prompt] of Object.entries(registeredPrompts as Record<string, Record<string, unknown>>)) {
+      if (typeof prompt['handler'] === 'function') {
+        prompt['handler'] = createWrappedHandler(prompt['handler'] as MCPHandler, 'registerPrompt', name);
+      }
+    }
+  }
+}
@@ -1,6 +1,6 @@
 import { getClient } from '../../currentScopes';
 import { fill } from '../../utils/object';
-import { wrapAllMCPHandlers } from './handlers';
+import { wrapAllMCPHandlers, wrapExistingHandlers } from './handlers';
 import { wrapTransportError, wrapTransportOnClose, wrapTransportOnMessage, wrapTransportSend } from './transport';
 import type { MCPServerInstance, McpServerWrapperOptions, MCPTransport, ResolvedMcpOptions } from './types';
 import { validateMcpServerInstance } from './validation';
@@ -18,17 +18,24 @@ const wrappedMcpServerInstances = new WeakSet();
  * and versions that expose the newer `registerTool`/`registerResource`/`registerPrompt` API (introduced in 1.x, sole API in 2.x).
  * Automatically instruments transport methods and handler functions for comprehensive monitoring.
  *
+ * Both call orderings are supported: wrapping before or after registering tools, resources,
+ * and prompts. Sentry patches the registration methods for future handlers and retroactively
+ * wraps any already-registered ones. Wrapping at construction time is recommended by
+ * convention (consistent with other SDK integrations), but is not required.
+ *
  * @example
  * ```typescript
  * import * as Sentry from '@sentry/core';
  * import { McpServer } from '@modelcontextprotocol/sdk/server/mcp.js';
  * import { StreamableHTTPServerTransport } from '@modelcontextprotocol/sdk/server/streamableHttp.js';
  *
- * // Default: inputs/outputs captured based on sendDefaultPii option
+ * // Wrap first, then register tools — this is the correct order
  * const server = Sentry.wrapMcpServerWithSentry(
  *   new McpServer({ name: "my-server", version: "1.0.0" })
  * );
  *
+ * server.registerTool('my-tool', schema, handler);
+ *
  * // Explicitly control input/output capture
  * const server = Sentry.wrapMcpServerWithSentry(
  *   new McpServer({ name: "my-server", version: "1.0.0" }),
@@ -80,6 +87,8 @@ export function wrapMcpServerWithSentry<S extends object>(mcpServerInstance: S,
 
   wrapAllMCPHandlers(serverInstance);
 
+  wrapExistingHandlers(serverInstance);
+
   wrappedMcpServerInstances.add(mcpServerInstance);
   return mcpServerInstance;
 }
@@ -2,7 +2,11 @@ import { beforeEach, describe, expect, it, vi } from 'vitest';
 import * as currentScopes from '../../../../src/currentScopes';
 import { wrapMcpServerWithSentry } from '../../../../src/integrations/mcp-server';
 import * as tracingModule from '../../../../src/tracing';
-import { createMockMcpServer, createMockMcpServerWithRegisterApi } from './testUtils';
+import {
+  createMockMcpServer,
+  createMockMcpServerWithPreregisteredHandlers,
+  createMockMcpServerWithRegisterApi,
+} from './testUtils';
 
 describe('wrapMcpServerWithSentry', () => {
   const startSpanSpy = vi.spyOn(tracingModule, 'startSpan');
@@ -145,6 +149,41 @@ describe('wrapMcpServerWithSentry', () => {
     });
   });
 
+  describe('Retroactive handler wrapping (handlers registered before wrapMcpServerWithSentry)', () => {
+    it('should replace executor/readCallback/handler on pre-registered entries with wrapped versions', () => {
+      const server = createMockMcpServerWithPreregisteredHandlers();
+      const { toolExecutor, resourceReadCallback, resourceTemplateReadCallback, promptHandler } = server._originals;
+
+      wrapMcpServerWithSentry(server);
+
+      expect(server._registeredTools['my-tool']!.executor).not.toBe(toolExecutor);
+      expect(server._registeredResources['res://my-resource']!.readCallback).not.toBe(resourceReadCallback);
+      expect(server._registeredResourceTemplates['my-template']!.readCallback).not.toBe(resourceTemplateReadCallback);
+      expect(server._registeredPrompts['my-prompt']!.handler).not.toBe(promptHandler);
+    });
+
+    it('should still wrap the registration methods for future handlers', () => {
+      const server = createMockMcpServerWithPreregisteredHandlers();
+      const originalRegisterTool = server.registerTool;
+
+      wrapMcpServerWithSentry(server);
+
+      expect(server.registerTool).not.toBe(originalRegisterTool);
+    });
+
+    it('should not double-wrap if called twice on the same instance with pre-registered handlers', () => {
+      const server = createMockMcpServerWithPreregisteredHandlers();
+
+      wrapMcpServerWithSentry(server);
+      const executorAfterFirstWrap = server._registeredTools['my-tool']!.executor;
+
+      wrapMcpServerWithSentry(server);
+      const executorAfterSecondWrap = server._registeredTools['my-tool']!.executor;
+
+      expect(executorAfterFirstWrap).toBe(executorAfterSecondWrap);
+    });
+  });
+
   describe('Handler Wrapping (register* API)', () => {
     let mockServer: ReturnType<typeof createMockMcpServerWithRegisterApi>;
     let wrappedServer: ReturnType<typeof createMockMcpServerWithRegisterApi>;
 
@@ -15,6 +15,41 @@ export function createMockMcpServer() {
   };
 }
 
+/**
+ * Create a mock MCP server that simulates already having tools/resources/prompts registered
+ * (i.e. wrapMcpServerWithSentry is called after registration). Mirrors the internal shape
+ * used by McpServer v2: tools have an `executor`, resources/prompts have `readCallback`/`handler`.
+ */
+export function createMockMcpServerWithPreregisteredHandlers() {
+  const toolExecutor = vi.fn().mockResolvedValue({ content: [] });
+  const resourceReadCallback = vi.fn().mockResolvedValue({ contents: [] });
+  const resourceTemplateReadCallback = vi.fn().mockResolvedValue({ contents: [] });
+  const promptHandler = vi.fn().mockResolvedValue({ messages: [] });
+
+  return {
+    registerTool: vi.fn(),
+    registerResource: vi.fn(),
+    registerPrompt: vi.fn(),
+    connect: vi.fn().mockResolvedValue(undefined),
+    server: { setRequestHandler: vi.fn() },
+    // Simulated internal registries (mirrors McpServer v2 private fields)
+    _registeredTools: {
+      'my-tool': { executor: toolExecutor },
+    },
+    _registeredResources: {
+      'res://my-resource': { readCallback: resourceReadCallback },
+    },
+    _registeredResourceTemplates: {
+      'my-template': { readCallback: resourceTemplateReadCallback },
+    },
+    _registeredPrompts: {
+      'my-prompt': { handler: promptHandler },
+    },
+    // Expose the original fns so tests can assert wrapping happened
+    _originals: { toolExecutor, resourceReadCallback, resourceTemplateReadCallback, promptHandler },
+  };
+}
+
 /**
  * Create a mock MCP server instance using the new register* API (SDK >=1.x / 2.x)
  */