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Automatic 'share by email' not working-config problem on my end?

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I had this feature working great for years but I seem to have broken something when I re-installed calibre as part of a win10 upgrade. Can anyone point out what I'm doing wrong?

Win10 PC, running Calibre 2.38 64bit

I have 2 recipes set for auto download and mail to 3 accounts. Will auto sent to only one of the 3 accounts. Account marked 'Jeff-Hotmail' works, other two accounts fail - see attached screenshot.

If I manually email the book from the GUI, emails to these same 2 accounts work fine. Calibre used to automatically email to same 2 accounts OK before re-install.

I'm sure it's something silly...but I can't seem to find it. Can someone point out what's not right? Thanks!

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