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I have Gmail. I need the same email content sent to the same person, at the first of each month. Is there a way to set that up to happen monthly without having to think about it or do any action?

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This is not something you can do natively in Gmail. You'll need a third-party service. – Al E. Sep 11 '13 at 13:37

You could use If This Then That.

This recipe will have an email sent on a specific day of the month. You also define the recipient address, the subject, the body of the email message and you can even provide an URL to attach a file.

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I recommend Boomerang for Gmail.

You could also connect your Gmail to an Outlook account and use Windows' built-in Task Scheduler to send an email through Outlook (from your Gmail account).

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