diff --git a/src/lib/utils.ts b/src/lib/utils.ts
index 940a8ca..280a489 100644
--- a/src/lib/utils.ts
+++ b/src/lib/utils.ts
@@ -2,6 +2,10 @@ import { OAuthClientProvider, UnauthorizedError } from '@modelcontextprotocol/sd
 import { SSEClientTransport } from '@modelcontextprotocol/sdk/client/sse.js'
 import { StreamableHTTPClientTransport } from '@modelcontextprotocol/sdk/client/streamableHttp.js'
 import { Transport } from '@modelcontextprotocol/sdk/shared/transport.js'
+
+// Connection constants
+export const REASON_AUTH_NEEDED = 'authentication-needed'
+export const REASON_FALLBACK_TO_SSE = 'falling-back-to-sse-transport'
 import { OAuthCallbackServerOptions } from './types'
 import express from 'express'
 import net from 'net'
@@ -80,6 +84,7 @@ export async function connectToRemoteServer(
   headers: Record<string, string>,
   waitForAuthCode: () => Promise<string>,
   skipBrowserAuth: boolean = false,
+  recursionReasons: Set<string> = new Set(),
 ): Promise<Transport> {
   log(`[${pid}] Connecting to remote server: ${serverUrl}`)
   const url = new URL(serverUrl)
@@ -101,23 +106,47 @@ export async function connectToRemoteServer(
     },
   }
 
-  const TESTING_NEW_TRANSPORT = true
-  const transport = TESTING_NEW_TRANSPORT
-    ? new StreamableHTTPClientTransport(url, {
-        sessionId: crypto.randomUUID(),
-      })
-    : new SSEClientTransport(url, {
-        authProvider,
-        requestInit: { headers },
-        eventSourceInit,
-      })
+  // Choose transport based on recursion history
+  let transport;
+  
+  if (recursionReasons.has(REASON_FALLBACK_TO_SSE)) {
+    log('Using SSEClientTransport due to previous protocol failure')
+    transport = new SSEClientTransport(url, {
+      authProvider,
+      requestInit: { headers },
+      eventSourceInit,
+    })
+  } else {
+    log('Trying StreamableHTTPClientTransport first')
+    transport = new StreamableHTTPClientTransport(url, {
+      sessionId: crypto.randomUUID(),
+    })
+  }
 
   try {
     await transport.start()
-    log('Connected to remote server')
+    log(`Connected to remote server using ${transport.constructor.name}`)
     return transport
   } catch (error) {
-    if (error instanceof UnauthorizedError || (error instanceof Error && error.message.includes('Unauthorized'))) {
+    // Check if it's a 405 Method Not Allowed error or similar protocol issue
+    if (error instanceof Error && 
+        !recursionReasons.has(REASON_FALLBACK_TO_SSE) &&
+        (error.message.includes('405') || 
+         error.message.includes('Method Not Allowed') ||
+         error.message.toLowerCase().includes('protocol'))) {
+      
+      // This condition is already checked above, so we will never reach here with REASON_FALLBACK_TO_SSE
+      // But keeping it as a safeguard
+      
+      log(`Received error: ${error.message}`)
+      log(`Recursively reconnecting for reason: ${REASON_FALLBACK_TO_SSE}`)
+      
+      // Add to recursion reasons set
+      recursionReasons.add(REASON_FALLBACK_TO_SSE)
+      
+      // Recursively call connectToRemoteServer with the updated recursion tracking
+      return connectToRemoteServer(serverUrl, authProvider, headers, waitForAuthCode, skipBrowserAuth, recursionReasons)
+    } else if (error instanceof UnauthorizedError || (error instanceof Error && error.message.includes('Unauthorized'))) {
       if (skipBrowserAuth) {
         log('Authentication required but skipping browser auth - using shared auth')
       } else {
@@ -131,12 +160,18 @@ export async function connectToRemoteServer(
         log('Completing authorization...')
         await transport.finishAuth(code)
 
-        // Create a new transport after auth
-        // TODO: this needs to be the same transport type as the originals
-        const newTransport = new SSEClientTransport(url, { authProvider, requestInit: { headers } })
-        await newTransport.start()
-        log('Connected to remote server after authentication')
-        return newTransport
+        if (recursionReasons.has(REASON_AUTH_NEEDED)) {
+          const errorMessage = `Already attempted reconnection for reason: ${REASON_AUTH_NEEDED}. Giving up.`
+          log(errorMessage)
+          throw new Error(errorMessage)
+        }
+        
+        // Track this reason for recursion
+        recursionReasons.add(REASON_AUTH_NEEDED)
+        log(`Recursively reconnecting for reason: ${REASON_AUTH_NEEDED}`)
+        
+        // Recursively call connectToRemoteServer with the updated recursion tracking
+        return connectToRemoteServer(serverUrl, authProvider, headers, waitForAuthCode, skipBrowserAuth, recursionReasons)
       } catch (authError) {
         log('Authorization error:', authError)
         throw authError