diff --git a/apps/server/src/api/services/chat-service.ts b/apps/server/src/api/services/chat-service.ts
index aefe92d73..9cd2ddcb5 100644
--- a/apps/server/src/api/services/chat-service.ts
+++ b/apps/server/src/api/services/chat-service.ts
@@ -18,24 +18,27 @@ import {
 } from '../../lib/clients/gateway'
 import type { KlavisClient } from '../../lib/clients/klavis/klavis-client'
 import { logger } from '../../lib/logger'
+import {
+  detectMcpTransport,
+  type McpTransportType,
+} from '../../lib/mcp-transport-detect'
 import type { BrowserContext, ChatRequest } from '../types'
 
-interface McpHttpServerOptions {
-  httpUrl: string
+interface McpServerOptions {
+  url: string
+  transport: McpTransportType
   headers?: Record<string, string>
   trust?: boolean
 }
 
-function createHttpMcpServerConfig(
-  options: McpHttpServerOptions,
-): MCPServerConfig {
+function createMcpServerConfig(options: McpServerOptions): MCPServerConfig {
   return new MCPServerConfig(
     undefined,
     undefined,
     undefined,
     undefined,
-    undefined,
-    options.httpUrl,
+    options.transport === 'sse' ? options.url : undefined,
+    options.transport === 'streamable-http' ? options.url : undefined,
     options.headers,
     undefined,
     undefined,
@@ -163,8 +166,9 @@ export class ChatService {
     const servers: Record<string, MCPServerConfig> = {}
 
     if (mcpServerUrl) {
-      servers['browseros-mcp'] = createHttpMcpServerConfig({
-        httpUrl: mcpServerUrl,
+      servers['browseros-mcp'] = createMcpServerConfig({
+        url: mcpServerUrl,
+        transport: 'streamable-http',
         headers: {
           Accept: 'application/json, text/event-stream',
           'X-BrowserOS-Source': 'gemini-agent',
@@ -182,8 +186,9 @@ export class ChatService {
           browserosId,
           browserContext.enabledMcpServers,
         )
-        servers['klavis-strata'] = createHttpMcpServerConfig({
-          httpUrl: result.strataServerUrl,
+        servers['klavis-strata'] = createMcpServerConfig({
+          url: result.strataServerUrl,
+          transport: 'streamable-http',
           trust: true,
         })
         logger.info('Added Klavis Strata MCP server', {
@@ -200,14 +205,22 @@ export class ChatService {
     }
 
     if (browserContext?.customMcpServers?.length) {
-      for (const server of browserContext.customMcpServers) {
-        servers[`custom-${server.name}`] = createHttpMcpServerConfig({
-          httpUrl: server.url,
+      const customServers = browserContext.customMcpServers
+      const transports = await Promise.all(
+        customServers.map((server) => detectMcpTransport(server.url)),
+      )
+      for (let i = 0; i < customServers.length; i++) {
+        const server = customServers[i]
+        const transport = transports[i]
+        servers[`custom-${server.name}`] = createMcpServerConfig({
+          url: server.url,
+          transport,
           trust: true,
         })
         logger.info('Added custom MCP server', {
           name: server.name,
           url: server.url,
+          transport,
         })
       }
     }
diff --git a/apps/server/src/lib/mcp-transport-detect.ts b/apps/server/src/lib/mcp-transport-detect.ts
new file mode 100644
index 000000000..ecef805a2
--- /dev/null
+++ b/apps/server/src/lib/mcp-transport-detect.ts
@@ -0,0 +1,106 @@
+/**
+ * @license
+ * Copyright 2025 BrowserOS
+ * SPDX-License-Identifier: AGPL-3.0-or-later
+ *
+ * Detects MCP transport type by probing the server endpoint.
+ *
+ * Following MCP spec (2025-03-26): try Streamable HTTP first, fall back to SSE.
+ * SSE transport is deprecated but still supported for older servers.
+ *
+ * @see https://modelcontextprotocol.io/specification/2025-03-26/basic/transports
+ */
+
+import { TIMEOUTS } from '@browseros/shared/constants/timeouts'
+import { logger } from './logger'
+
+export type McpTransportType = 'streamable-http' | 'sse'
+
+const CACHE_TTL_MS = 60 * 60 * 1000 // 1 hour
+
+interface CachedTransport {
+  transport: McpTransportType
+  expiresAt: number
+}
+
+const transportCache = new Map<string, CachedTransport>()
+
+export async function detectMcpTransport(
+  url: string,
+): Promise<McpTransportType> {
+  const cached = transportCache.get(url)
+  if (cached && Date.now() < cached.expiresAt) {
+    return cached.transport
+  }
+
+  let transport: McpTransportType
+  let shouldCache = true
+  try {
+    const response = await fetch(url, {
+      method: 'POST',
+      headers: {
+        'Content-Type': 'application/json',
+        Accept: 'application/json, text/event-stream',
+      },
+      body: JSON.stringify({
+        jsonrpc: '2.0',
+        id: 0,
+        method: 'initialize',
+        params: {
+          protocolVersion: '2025-03-26',
+          capabilities: {},
+          clientInfo: { name: 'browseros-probe', version: '1.0.0' },
+        },
+      }),
+      signal: AbortSignal.timeout(TIMEOUTS.MCP_TRANSPORT_PROBE),
+    })
+
+    const contentType = response.headers.get('content-type') ?? ''
+    const isJsonResponse = contentType.includes('application/json')
+    const isStreamResponse = contentType.includes('text/event-stream')
+
+    // Release the connection — avoid leaking open streams (especially SSE)
+    await response.body?.cancel()
+
+    logger.debug('MCP transport probe response', {
+      url,
+      status: response.status,
+      contentType,
+    })
+
+    if (response.status === 200 && (isJsonResponse || isStreamResponse)) {
+      transport = 'streamable-http'
+    } else if (response.status === 401) {
+      transport = 'streamable-http'
+    } else if (response.status >= 500) {
+      transport = 'sse'
+      shouldCache = false
+    } else {
+      transport = 'sse'
+    }
+  } catch (error) {
+    logger.debug('MCP transport probe failed', {
+      url,
+      error: error instanceof Error ? error.message : String(error),
+    })
+    transport = 'sse'
+    shouldCache = false
+  }
+
+  if (shouldCache) {
+    transportCache.set(url, {
+      transport,
+      expiresAt: Date.now() + CACHE_TTL_MS,
+    })
+  }
+  logger.debug('Detected MCP transport', {
+    url,
+    transport,
+    cached: shouldCache,
+  })
+  return transport
+}
+
+export function clearTransportCache(): void {
+  transportCache.clear()
+}
diff --git a/packages/shared/src/constants/timeouts.ts b/packages/shared/src/constants/timeouts.ts
index 405e6ff42..69fa07f76 100644
--- a/packages/shared/src/constants/timeouts.ts
+++ b/packages/shared/src/constants/timeouts.ts
@@ -17,6 +17,7 @@ export const TIMEOUTS = {
 
   // MCP operations
   MCP_DEFAULT: 5_000,
+  MCP_TRANSPORT_PROBE: 5_000,
 
   // External API calls
   KLAVIS_FETCH: 30_000,