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I have some custom fields on the Opportunity page layout; one captures the contact name and one is for the contact email. These are formula fields that query the contact roles related list. Once the fields are populated, I want to create a list view with Opportunities that have closed in the past 30 days and send out a mass email to them; don't want to automate this as I want to have the flexibility to deselect a few opportunities based on our discretion. How would I configure a custom button to send a mass email to those contacts at the respective contact email address and have the ability to select an email template which has fields mapped to the Opportunity record?

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Here is how I would do it. Have a custom setting to store the email template ID or email template name on it. Whenever you need to change the template, you can change it.

Create a list button, and a Visualforce page. Let the controller behind the Visualforce pick the email template from the custom setting, the email address from the opportunity and fire the email.

Here is an example: https://developer.salesforce.com/docs/atlas.en-us.pages.meta/pages/pages_controller_sosc_custom_button.htm

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