Is anyone able to email pictures using gmail?

Configuration
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OK, dug deeper into the account used for HA automations (which is not my main Google Account or gmail). Yes it reports 2 factor has been on since middle of 2022 on the HA account login.
I’ve turned it off, on just the HA account.

Tried again to send email via SMTP. Still failed so far. I will try looking for issues I may have caused in debugging with many config changes…

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I think what schmuttis was hinting at was that you need 2FA and to generate a App password, your account password will not work.

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