Google have deprecated and will eventually remove the ability to send email using their SMTP server with your normal Gmail password (it will work until June 2020 if allow insecure apps is turned on in your Google account settings). Going forward, you must create a separate app-specific password to use Gmail’s SMTP server.
Here are the steps:
- Log into your Google Account in a web browser at https://myaccount.google.com
- Click your account icon (top right) and choose Manage Your Google Account
- Click Security in the left hand sidebar
- In the Signing in to Google box, turn on 2-step Verification — this is required by google for app-specific passwords (you may have to jump through some verification hoops to complete this step).
- You now have an App Passwords option in the Signing in to Google box — click it
- Click Select App and choose Other
- For the name, type MoneyWorks SMTP, or similar and click Generate
- You will be given an auto generated password — right-click it and Copy
- In MoneyWorks, select Edit > MoneyWorks Preferences and click the Emailing tab
- Enter smtp.gmail.com for the SMTP server
- Enter your gmail address into the From field
- Turn on Use Authentication and enter your gmail address for the Username
- Paste in the app-specific password you copied in step 8
- Click Test. You should receive an email in your gmail account
If for some reason the Test returns an error, set the SMTP server to smtp.gmail.com:587 and try again. If this fails, you may need to contact your ISP.