diff --git a/cli/package.json b/cli/package.json
index ca1bea454..0dc83ead5 100644
--- a/cli/package.json
+++ b/cli/package.json
@@ -28,6 +28,7 @@
   "scripts": {
     "build": "tsdown",
     "dev": "NPMX_CLI_DEV=true node src/cli.ts",
+    "dev:debug": "DEBUG=npmx-connector NPMX_CLI_DEV=true node src/cli.ts",
     "test:types": "tsc --noEmit"
   },
   "dependencies": {
diff --git a/cli/src/npm-client.ts b/cli/src/npm-client.ts
index 1c1cb270f..b709e77fa 100644
--- a/cli/src/npm-client.ts
+++ b/cli/src/npm-client.ts
@@ -7,7 +7,7 @@ import { tmpdir } from 'node:os'
 import { join } from 'node:path'
 import * as v from 'valibot'
 import { PackageNameSchema, UsernameSchema, OrgNameSchema, ScopeTeamSchema } from './schemas.ts'
-import { logCommand, logSuccess, logError } from './logger.ts'
+import { logCommand, logSuccess, logError, logDebug } from './logger.ts'
 
 const execFileAsync = promisify(execFile)
 
@@ -75,10 +75,15 @@ function detectOtpRequired(stderr: string): boolean {
     'EOTP',
     'one-time password',
     'This operation requires a one-time password',
+    'OTP required for authentication',
     '--otp=<code>',
   ]
   const lowerStderr = stderr.toLowerCase()
-  return otpPatterns.some(pattern => lowerStderr.includes(pattern.toLowerCase()))
+  logDebug('Checking for OTP requirement in stderr:', stderr)
+  logDebug('OTP patterns:', otpPatterns)
+  const result = otpPatterns.some(pattern => lowerStderr.includes(pattern.toLowerCase()))
+  logDebug('OTP required:', result)
+  return result
 }
 
 function detectAuthFailure(stderr: string): boolean {
@@ -96,7 +101,11 @@ function detectAuthFailure(stderr: string): boolean {
     'npm adduser',
   ]
   const lowerStderr = stderr.toLowerCase()
-  return authPatterns.some(pattern => lowerStderr.includes(pattern.toLowerCase()))
+  logDebug('Checking for auth failure in stderr:', stderr)
+  logDebug('Auth patterns:', authPatterns)
+  const result = authPatterns.some(pattern => lowerStderr.includes(pattern.toLowerCase()))
+  logDebug('Auth failure:', result)
+  return result
 }
 
 function filterNpmWarnings(stderr: string): string {
@@ -123,6 +132,7 @@ async function execNpm(
   }
 
   try {
+    logDebug('Executing npm command:', { command: 'npm', args: npmArgs })
     // Use execFile instead of exec to avoid shell injection vulnerabilities
     // On Windows, shell: true is required to execute .cmd files (like npm.cmd)
     // On Unix, we keep it false for better security and performance
@@ -132,6 +142,8 @@ async function execNpm(
       shell: process.platform === 'win32',
     })
 
+    logDebug('Command succeeded:', { stdout, stderr })
+
     if (!options.silent) {
       logSuccess('Done')
     }
@@ -144,6 +156,7 @@ async function execNpm(
   } catch (error) {
     const err = error as { stdout?: string; stderr?: string; code?: number }
     const stderr = err.stderr?.trim() ?? String(error)
+    logDebug('Command failed:', { error, stdout: err.stdout, stderr: err.stderr, code: err.code })
     const requiresOtp = detectOtpRequired(stderr)
     const authFailure = detectAuthFailure(stderr)