Sending Emails from Image for Windows to Gmail Server Fails

Problem:

Emails sent from Image for Windows to Gmail server fail.

Cause:

Google blocks apps and devices it considers less secure from accessing the account using the normal login details.

Solution:

Create a Google account app password to use with Image for Windows. The app password along with 2-Step verification gives a less secure app permission to access the Google account.

Create Google Account App Password:

1. Sign into your Google Account: https://myaccount.google.com/
   
   
2. Once signed in, click the Security section (this may be on the left side of the page or across the top depending on the page size).
   
   
   
   
3. In the Signing in to Google section, ensure that 2-Step Verification is enabled. If not, you will need to click that section and enable it before the App passwords section will be available for selection. Note: If 2-Step Verification is only set up for security keys you will not be able to use app passwords.
   
   
   
   
4. In the Signing in to Google section, click the App passwords section (enter your password if prompted).
   
   
   
   Note: If the App passwords option is not available it may be because:
• 2-Step Verification is not set up for your account
• 2-Step Verification is only set up for security keys
• Your account is through work, school, or other organization
• You turned on Advanced Protection
  
  
5. On the App passwords screen, under Select the app and device you want to generate the app password for, click the Select app drop-down and select the Other (Custom name) option.
   
   
   
   
6. Enter the name for the app password. For example: IFW-Email
   
   
   
   
7. Click the GENERATE button to create the password.
   
   
8. The generated app password will be displayed. Copy or make note of the 16-character password to use with Image for Windows.
   
   

Configure Image for Windows to use App Password

1. Run Image for Windows and go into Settings.
   
   
2. On the Email tab, configure the settings as follows. Use your gmail.com email login address (myemail@gmail.com is used in this example) and the app password you created.
   Server: smtp.gmail.com
   Port: 587 TLS
   User: myemail@gmail.com
   Password: <enter your App Password here>
   
   Configure the remaining email fields as desired for the emails.
   
   
   
   
3. Click the Test button to send a test email.

Note: If the email fields are configured correctly and Image for Windows is still not sending operation emails, make sure the log level option to flush logging is disabled (if enabled, emails will not be sent). This option is LogLevel in the ifw.ini file or /logl on the command line. Details on this option can be found in the Image for Windows manual.

For more details, reference the Google support article on creating and signing in with app passwords:
https://support.google.com/accounts/answer/185833