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Gmail - Google Mail with System Five

This document is also available as a FreshDesk Solution Article


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

Be aware that 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 doesn'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.
  • Return address will be the user's full Gmail address
  • Mail Server (Incoming) will be
  • Login Name will again be the user's full email address.
  • SMTP Server (Outgoing) will be (Gmail recommends either Port: 465 or 587) .
  • Password will be the password for the user's Gmail account.
  • 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.

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.

Also 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.

Configure and email PDF Invoices

Created by Steve Wind May 13 2019
Updated by Steve Wind April 21 2020

gmail_google_mail_with_system_five.txt · Last modified: 2022/01/13 11:34 (2 years ago) by swind