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Is there a way, either in Gmail, Boomerang or in another lab/extension to create a reminder in your GCal (Google Calendar) To Do List?

So, before sending the email, there would need to be a place to enter the reminder date/time/message and which task list it would be added to, would it be placed at the top or bottom of the list, and so on.

This would be more helpful rather than either returning the message, re-sending the message at a fixed (or random) time in the future, etc. This would require Gmail and GCal to communicate with each other, either by themselves or via Boomerang. Is this possible?

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Almost, but not quite. (At least, with Gmail and Google Calendar alone.)

While you're reading your message, open the "More" menu and choose "Add to Tasks".

"More" menu

This will add a task to your Google Tasks with the subject of your message as the text of the task and a link to the email message.

Added to Tasks

Click the arrow to go to the "more" menu for that item.

More options for Task item

Then choose a due date.

Choose a due date

While you're there you can move it to a different list, if necessary.

The task will appear on your calendar as a to-do item.

Task item on calendar

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