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Upgrade your OctoPrint installation of yagmail with:

> oprint/bin/pip-2.7 install yagmail[all] --upgrade

(Note that oprint/bin pip/python environment is separate from the system pip/python environment.)

Currently testing with yagmail 0.6.161. Confirm version with:

> oprint/bin/python
>>> import yagmail
>>> yagmail.__version__
'0.6.161'

Source of many issues with EmailNotifier is yagmail installation and setup.