If you want to use GMail or Yahoo Mail with Mail Merge or Web Prospect there are a few settings on your account that will need to be adjusted.
First, you can't have 2-step authentication enabled on your Gmail account. Second, you need to enable "less secure apps" in your Gmail account.
For Yahoo, you can edit these settings at https://login.yahoo.com/account/security.
For the account settings, you should be using the following for Gmail:
- SMTP server = smtp.gmail.com
- SMTP Login Username = your Gmail address
- SMTP Login Password = your Gmail password
- From Email Address = your Gmail address
- Port = 587 with use SSL/TLS checked (on)
For Yahoo Mail, use these settings:
- POP server = pop.mail.yahoo.com
- SMTP server = smtp.mail.yahoo.com
- Login Username = your Yahoo address
- Login Password = your Yahoo password
- POP Port = 995 with use SSL/TLS checked (on)
- SMTP Port = 587 with use SSL/TLS checked (on)
- From Email Address = your Yahoo address
If you do not use these settings, you will see a "socket error" when trying to connect to your account when you click the "test mail settings" button.