2) Also, scenerio: John Doe from Widget.Com is a vendor we deal with.
During the day, he sends his email from work at widget.com.  At night, he
also conducts business from his house using his widget.com "from" address,
but must authenticate through his ISP's server rather than widget.com.

Will using SPF reject this?

No.

Or, if it does, it is an issue with the way that the people that own the widget.com domain set up SPF.

Specifically, the owners of widget.com domain needed to decide if John could send from his ISP at night. If not, SPF should reject it. If so, either SPF will result in a neutral response (for John, as well as spammers using a fake address @widget.com), or the owners of widget.com can add John's ISP to the SPF record (which is more work, but helps more spam get blocked).
                               -Scott


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