Troubleshooting Print to Email

some reference material here https://docs.microsoft.com/en-us/exchange/mail-flow-best-practices/fix-issues-with-printers-scanners-and-lob-applications-that-send-email-using-off

If you are printing to email via a google account remember to turn on “Allow less secure apps” on the account or you won’t be able to print to email. the error messages are spectacularly unhelpful.

Sign into the google.com web account that you want to use to scan to email or send alerts

click the 9 dots in the top right

click account

click security

scroll down to Less secure app access and turn it on

I have noticed this get turned off (by google?) very infrequently