Use 2-Step Verification to Send Emails via Gmail
The AutoMailMerge can send emails with PDF attachments to the recipients listed in the spreadsheet or any other data file. To configure, you must give AutoMailMerge an SMTP server it can use for sending the e-mails. Many organizations have an internal SMTP server you can use and hosting companies often provide one as well. Widely popular Gmail provides an SMTP server that you can use to send up to 2,000 messages a day. This tutorials tells you how to set up Gmail as an SMTP server when your Google account is configured with 2-factor authentication.
For increased security your Google account may be using 2-factor authentication, also known as 2-step verification. When enabled, you must log in to Gmail with both your password and your phone. This prevents hackers who get your password from getting into your account, since they won’t get the security code sent to your phone.
This method requires App Passwords to be used to send emails from the plug-in. An App Password is a 16-digit passcode that gives a non-Google app or device permission to access your Google Account. App Passwords can only be used with accounts that have 2-Step Verification turned on.
Step 1 - Enable 2-Factor Authentication in Google Account
Open a web browser and login into your Google account. Click on "Security" menu (it can be located on the left or at the top of the webpage).
Step 2 - Select "2-Step Verification"
If "2-Step Verification" is not turned on, then click on the it to enabled it.
Step 3 - Configure 2-Step verification
Click the "Get Started" button to start configuring the 2-step verification options.
You may be prompted to login into your Google account one more time to confirm your identity:
Step 4 - Use your Phone to Complete Configuration
Use on-screen instructions and available options to complete 2-Step verification using your phone.
Step 5 - Create the App Password
Click on "App Password" option to create a new application password for use with the AutoMailMerge:
Step 6 - Add New App Name
First, select a device (for example, Windows Computer) and then click on "Select App" menu and choose "Other (custom name)":
Enter AutoMailMerge as an app name (it really does not matter what name is used in this field). Click "Generate" button:
Record the auto-generated app password or simply select it and copy to the clipboard for the later use.
Step 7 - Enter Password into AutoMailMerge Settings
Start Adobe Acrobat and select "Plug-ins > Mail Merge..." from the menu. Click "Edit Settings" button and press "Next>>" button repeatedly to navigate to "E-mail Server Type" settings screen. Select "Use SMTP Internet E-mail Server" option and press "Next>>" button:
Type (or paste) the app password into a "Password" field. Fill the rest of the required fields, including "User Name".
Next, press "Advanced Server Settings" and configure server parameters for use with Gmail server.
Step 8 - Test Server Settings
Press "Test Server Settings" button to check if you can connect to the Gmail SMTP server.
If the connection was successful, then the following confirmation message will appear on the screen:
Now you have succesfully configured AutoMailMerge to use 2-step verification and app-passwords.