Settings SMTP Email Configuration

Use KeePass with Pleasant Password Server

Simple Mail Transfer Protocol (SMTP) configuration is included in many Pleasant Password Server features, however, Email integration is optional.

Sections:

• Initial Email Setup
• Test SMTP Email
• Confirm User Email Addresses
• Email Setup with Office 365
• Troubleshooting

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

Initial Email Setup

Note: Email setup is optional.

Step 1: Configure Email

To setup email integration, navigate to: the Web Application > Settings menu > Email 

•  Specify Username/Password, or not (screenshots)

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 Host Address:

• The URL or IP address of your SMTP Server.

SMTP Port Number:

• Port 587 is the default
• Check if your SMTP server supports STARTTLS over port 587
• Port 25: Note that this port is blocked by Azure VM's

Test SMTP Email

Step 2: Test

• Click Save
  • First, the SMTP configurations must be saved before a test email can be sent.

• Click Test SMTP

  • Checks that the SMTP configuration is valid, by sending to a specified email address.

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

Confirm User Email Addresses

Step 3: Ensure users will receive the email

Users require a valid, confirmed email address, without which they will not receive email notifications. Directory users' email addresses will be imported and auto-confirmed.

• Click 'Confirm'  - for Local users email address:
  • Ensure valid email addresses are entered and confirmed for local users. 
  • Navigate to:
    • Users and roles > Click on user's profile
    • Click the Confirmed? checkbox for the email address.

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.office365.com
   • 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.

Troubleshooting

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 (section "Email Logging")
  • 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

  • You may be seeing an error like this: "No connection could be made because the target machine actively refused it"
  • Is SMTP traffic going through your firewall? If not, you have a firewall blocking outbound email, and 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)

• Port 25

  • Note that Azure blocks Port 25 by default.

• 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.