Software⏱️ 4 min read📅 2026-06-11

How to Fix: Telnet 555 5.5.2 Syntax error. b42si7464989qgd.93 - gsmtp

Telnet error due to unrecognized command in Gmail SMTP server. Use STARTTLS for secure connection.

Quick Answer: Use the correct command 'MAIL FROM:' followed by the sender's email address, and enable STARTTLS for a secure connection.

The error 'Telnet 555 5.5.2 Syntax error. b42si7464989qgd.93 - gsmtp' is encountered when attempting to send email using Telnet and Gmail as the SMTP server. This issue affects users who are trying to use Telnet for email spoofing or relaying purposes.

It's frustrating because it prevents users from successfully sending emails, which can be a critical task in various scenarios such as email marketing campaigns, automated tasks, or even just personal communication. In this guide, we will explore the root causes of this error and provide two primary fix methods to resolve the issue.

⚠️ Common Causes

  • The first main reason for this error is that Gmail has strict policies against relaying emails through third-party servers, including Telnet. This is done to prevent spam and phishing attacks. When a user attempts to send an email using Telnet, Gmail recognizes it as an unauthorized relay and returns the 5.5.1 Unrecognized command error.
  • The second alternative reason could be related to the specific syntax or formatting of the commands used in the Telnet session. However, this is less likely to be the cause of the error, as the provided sequence of commands follows standard Telnet protocol guidelines.

🔧 Proven Troubleshooting Steps

Using a Disposable Email Provider

  1. Step 1: Create an account on a disposable email provider such as Dispostable.com. This will give you a temporary email address that can be used to send emails without being tied to your personal Gmail account.
  2. Step 2: Set up the Telnet connection using the new disposable email address as the 'FROM' address. Make sure to use the correct SMTP port (25) and server address (alt3.gmail-smtp-in.l.google.com).
  3. Step 3: Send the email using the Telnet commands, making sure to follow the standard protocol guidelines. If you encounter any issues, try adjusting the formatting or syntax of your commands.

Configuring Gmail to Allow Outgoing Mail Relaying

  1. Step 1: Create a new Gmail account specifically for sending emails using Telnet. This will help keep your personal Gmail account secure and prevent any potential spam issues.
  2. Step 2: Go to the Google Workspace Admin Console (or individual admin settings) and navigate to 'Security' > 'Less secure apps'. Enable the 'Allow less secure apps' option to allow outgoing mail relaying. Note that this may increase security risks, so use caution when enabling this setting.
  3. Step 3: Set up the Telnet connection using the new Gmail account as the 'FROM' address. Make sure to use the correct SMTP port (25) and server address (alt3.gmail-smtp-in.l.google.com).
  4. Step 4: Send the email using the Telnet commands, making sure to follow the standard protocol guidelines.

🎯 Final Words

To resolve the 'Telnet 555 5.5.2 Syntax error' issue, you can either use a disposable email provider like Dispostable.com or configure Gmail to allow outgoing mail relaying by enabling the 'Allow less secure apps' option in the Google Workspace Admin Console. By following these steps, you should be able to successfully send emails using Telnet and Gmail.

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