Simple Mail Transfer Protocol (SMTP) configuration is integral to many Pleasant Password Server features.

Authentication

The SMTP protocol will attempt to connect using a compatible authentication method supported by your SMTP server.

Note: We explicitly do not support XOAUTH2 as a mechanism

Enable SSL

  • If TLS is required by your email provider, then select this option.

Username & Password:

  • These fields remain blank, if no authentication is required.
  • However, if the Username is provided than a password is needed as well.

Test SMTP Email

Click the "Test SMTP" button:

  • The Email attempt will display this message:
    • "Attempting to send a test email to __________________"

Troubleshooting

If you are unable to receive a test email check the steps below.

  • View Email Logging Details
    • Get more Detailed Logging information for Email
    • If you see an "Account is not valid" error:
      • Double-check the settings / username & password. Perhaps Username & Password can remain blank, but otherwise if required, provide both username & password

  • White-list this IP on your email gateway

  • Is Firewall / Anti-virus Blocking Outbound Emails
    • Is SMTP traffic going through your firewall?
    • If you have a firewall blocking outbound email, the process to exclude is:

"%ProgramFiles(x86)%\Pleasant Solutions\Pleasant Password Server\PassMan.WindowsService.exe"

(Note: this location is the default install directory, but may have been changed to another folder)

  • Host Address / IP Resolution
    • Ensure your host address resolves to the correct IP address, and not to a other/secondary machine, etc.

  • Authentication Method
    • Check that the SMTP server is accepting authentication with your SMTP username and password.

  • Check SPAM / Junk Filters
    • If necessary, add email address as a contact to avoid SPAM filters

  • Identity Provider Requires 2FA
    • Using another MFA tool that requires 2FA for the email integration
    • Since the SMTP email connection does not integrate with 2FA, you may require a special bypass rule that does not require 2FA

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