This will work in both the On-Premises version of System Five and in the System Five On Cloud environment. 


Microsoft Outlook configured with Gmail is a better user experience since it allows you to see what emails are being sent and received. With the Google Gmail setup, System Five is handling the sending of emails, and you are not able to track whether an email has been sent without opening a web browser and logging into Gmail to see if your email is going out.
You don't need the virtual channel or the Remote POS Device Manager if Gmail is being used for sending emails from within System Five. To be clear It is only utilized to send emails from within System Five. System Five doesn't receive emails.
 This Gmail setup does have it's limitations. We only present it as a solution for people that either don't have Outlook or don't want to invest in purchasing Outlook. 


You will need to have a functional Google Gmail account before you set this up.  If you don't have one you can get one here.
Create Your Gmail Account 

Gmail Settings

To enable POP in Gmail. Don't forget to click Save Changes when you're done. 

  •  On your computer, open Gmail.
  •  In the top right, click Settings icon.
  •  Click Settings in the dropdown.
  •  Click the Forwarding and POP/IMAP tab.
  •  In the “POP download” section, select Enable POP for all mail or Enable POP for mail that arrives from now on.
  •  At the bottom of the page, click Save Changes.

System Five Setup

  •  Open System Five.
  •  Open the Setup Wizard.
  •  Click on Users.
  •  Double click on the user account you want to set up the email for (In my demo I just used the Demo user).
  •  Click on the Internet tab, and configure System Five with the settings as shown.


  •  Email Options should be set to Email Directly.
  •  Real Name will be the real name of the user. eg Mary Smith, Joe Blow, John Smith.
  •  The Return address will be the user's full Gmail address 
  •  Mail Server (Incoming) will be pop.gmail.com:995    
  •  The Login Name will again be the user's full email address.
  •  SMTP Server (Outgoing) will be smtp.gmail.com:587  (Gmail recommends either Port: 465 or 587) .
  •  Password will be the App password generated for System 5
  •  Confirm is again the user's Gmail account.
  •  Use SMTP Aut6hentication must be checked.
  •  Use SSL must be checked.

If you are getting access violations when trying to send invoices through Gmail, you may need to change the incoming POP port from :995 to :465
 Even though we don't import emails into System Five, this incoming mail server setting must be there and set to a valid POP Address and port.  

Additional Gmail Links

Error Messages

 - If you get an error saying invalid credentials, check that you have entered your password correctly in the email settings of System Five. 

 - The error below could also point to invalid credentials.

 - If you are getting SSL Timeouts or SSL Authentication errors, two things may be causing the issue.

1. you can try setting the Incoming POP port from :995 to :465 and the Outgoing SMTP Server to :587.

2. Verify that your Gmail account allows “Less Secure” email programs to access Gmail.

  •  To do this, sign into Gmail through your web browser.
  •  Click your photo, avatar or outline near Gmail's top right corner.
  •  Click Manage Your Google Account.
  •  Click Security on the left side of the screen.
  •  Scroll down till you see Less Secure App Access.
  •  click on “Turn on access (not recommended)”.
  • Click the little slide switch next to “Allow Less Secure Apps: Off”.
  • The little slide switch will move to the right and change color.
  •  You can now close the browser tab.

Select Sign-in & security. 

Make sure Allow less secure apps is On. 

 - If you are getting the error below saying "No Mail Client installed or configured..."

The issue is being caused by the "Connect to Outlook via OLE Automation" being checked in the user settings. 

Even though this setting is greyed out it is still causing System Five to look for an email client. 

To disable it you will have to set the Email Option to "Email through your email client" to be able to uncheck the "Connect to Outlook via OLE Automation"  check box, and then re-select "Email Directly" Option, then click the OK button to exit.

Other Email Setups and Configuration

The following video will show the configuration settings and method for generated invoices in the PDF format and sending by email. 


When will the change occur?

            May 30th, 2022

What is the change?

Users of email through System Five will need to connect using an application password instead of account credentials.

Why is the change occurring?

Google will no longer support the use of third-party apps or devices which ask you to sign into your Google Account using only a username and password. This will cause an issue for those using email from System Five. A solution has been found to allow users to connect using an application password instead of account credentials. 


What changes need to be done for the customer?

Add an App Password

  1. 2 Step Verification must be enabled to use an App Password
  2. In the App passwords page select “other” as the app you are using and name it “System 5 – Email”.
  3. Next, select the device you are using System Five on.
  4. Finally, generate the password by selecting the generate button at the bottom of the page and copy the 16-digit password and paste it into the application.


For more information, please see the link https://support.windwardsoftware.com/a/solutions/articles/66000505012 for more info.

Created by Steve Wind May 13 2019
Updated by Steve Wind January 13 2022