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My grandfather has on his laptop Outlook 2016, which contains both his and my grandmother's 2 separate Outlook accounts.

But whenever he emails on behalf of my grandfather, often my grandfather forgets to change the 'From:' field, indicated by the red arrows: enter image description here

So to resolve his forgetfulness, he wishes Outlook to force him to choose which email account from which to send an outgoing email, every time he does so.

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Try this: goto File > Options > Mail, then uncheck "Always use default account when composing new messages"

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