Prerequisites
- Your mySMTP username and password from the setup email
- Your mySMTP hostname from the setup email (shown as
relayxx.mysmtp.comin these examples) - swaks, OpenSSL, or telnet installed on your system
Test with swaks
swaks is a command-line SMTP testing tool that handles authentication and TLS automatically.Install swaks
Send a test email
Replace
relayxx.mysmtp.com, YOUR_USERNAME, and YOUR_PASSWORD with your real hostname and credentials from the setup email.Test TLS with OpenSSL
Use OpenSSL to inspect the TLS handshake and send a manual SMTP session.STARTTLS on port 587
334 VXNlcm5hbWU6, which is the Base64 prompt for username. Encode your username and password in Base64:
Implicit TLS on port 465
Verify port reachability
Windows (PowerShell)
Linux and macOS (telnet)
220 relayxx.mysmtp.com ESMTP. Type QUIT to close. If the connection times out, the port is blocked by a firewall or ISP.
Linux and macOS (nc)
Automated online testing
Run a full deliverability and authentication test at test.smtp.ai. It checks port connectivity, TLS negotiation, authentication, and DNS records in one step.Common errors
535 Authentication failed
535 Authentication failed
Your username or password is incorrect, or your account is not yet activated. Re-enter credentials exactly as shown in the setup email. See Setting up SMTP credentials.
Connection timeout or refused
Connection timeout or refused
Your network or host may block port 587. Try port 2525 with the same swaks command, or port 465 with OpenSSL. See Supported SMTP ports and encryption.
TLS handshake failure
TLS handshake failure
The OpenSSL flags do not match the port. Use
-starttls smtp for ports 587 and 2525. Use -connect without -starttls for port 465..png?fit=max&auto=format&n=-Uw4rR8wfyv_xkzc&q=85&s=898bb0b43b6c9dce61441f46ac9ac860)