Settings SMTP Email Configuration

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


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.

SMTP Port Number:

  • Currently only port 587 is supported
  • Using Port 465 with SSL/TLS - is not supported
    • Check if your SMTP server supports STARTTLS over port 587


SMTP Email config

Test SMTP Email

Click the "Test SMTP" button:

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

Email Setup with Office 365

Here are instructions for integrating with Office 365 Email:

  1. Log into your Password Server > click on Settings > then Email
  2. In the 'Edit SMTP Configuration' page, enable the 'Enable SMTP' and 'Enable SSL' and fill out the fields using this guide:
    • (These fields may be optional):
      • SMTP Username: <email address>
      • SMTP Password: [password to authenticate above email address]
    • SMTP From Email: <email address, same as above>
    • SMTP Host Address:
    • SMTP Port Number: 587
  3. Review the settings and click on 'Save'.
  4. Click on 'Test SMTP' then enter an email address to test the settings.
  5. Click on 'Send Test Email' and check the mailbox for the test account.


If you are unable to receive a test email check the possible problems 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
    • Your SMTP server may be expecting an authentication method that is not supported. If TLS is required, then enable it.

    • 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

  • Bypass 2FA / 2-Step Verification
    • The SMTP email connection does not integrate with 2FA
      • Remove any requirements for 2FA or 2-step verification from the Email Configuration
      • You may require a special bypass rule that does not require 2FA
  • Certificate issues
    • If you see a certificate error in the log please consult our trust warnings wiki for more information here.