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There are some special issues when configuring ACCOUNTS to send email through a Gmail address, because Google introduced what it considers to be a higher level of security for applications other than the most common email software (like Microsoft Outlook) to send and receive emails through Gmail. Although Google refers to such applications as "insecure", in fact ACCOUNTS and most others are still very secure, using encryption to protect your password and the email contents! (No other email service insists on such steps, or calls other programs like this "insecure".)
If you try to configure using a Gmail address in Maintenance ⇒ Email Sending Configuration window, and the SMTP Server you set up there is "smtp.gmail.com" (the current correct one for Gmail), you will probably receive a large message box about there being a problem doing this, and offering you two main buttons for options: Grant Access for Less Secure Apps, and Authorize ACCOUNTS.
This page explains those two options.
Grant Access for Less Secure Apps
This first option grants access to your Gmail account, as long as you supply the correct username (your email address) and password, to all applications that Gmail considers to be insufficiently secure, including ACCOUNTS. Clicking it will take you to a page in a web browser. If you aren't currently logged in to Gmail (or another Google service with the same account), it will first take you to a page where you can log in to the desired account. After doing that, you will end up on a page such as the following:
If you click the "Turn on" radio button, it will immediately turn that on. Close that window (or minimize it) to return to ACCOUNTS, and then follow the prompts to try emailing again, and it should work. If it doesn't, please double-check that you have entered the correct Gmail password in the Password field in the configuration window (click "Make password visible, rather than stars" below that field, to make sure you can see it).
This option is very different - it allows you to grant authorization only for ACCOUNTS to access your Gmail account, not all other applications that Google considers to be "insecure". Although the authorization would technically allow it to both send and retrieve your Gmail emails, the program never retrieves them - it only sends them, and only when you use menu options that are clearly doing so.
If you click this button, it will take you to a page in a web browser (embedded in a window from ACCOUNTS). If you aren't currently logged in to Gmail (or another Google service with the same account), it will first take you to a page where you can log in to the desired account. After doing that, you will end up on a page such as the following:
Click the Allow button, and it will show you a page like the following:
Just close the window, or click the Done, return to ACCOUNTS button (which also closes the window), and then follow the prompts. It will try sending your email again, and it should work.
As long as you don't change your email account in Maintenance ⇒ Email Sending Configuration, it should just keep working from then on.
If you ever change your Gmail password, the authorization you have granted will be invalidated, and you will have to re-do it.
What if the Authorization Fails?
Some users have found that the authorization set in the 2nd option above starts failing, even if they didn't change their Gmail password. The easiest thing to do in that case is to go back to the other option.
To do that, first, clear the saved Gmail information by entering “NONE”, without the quotes, into the SMTP Server field in the Maintenance ⇒ Email Sending Configuration window, then clicking OK.
Then go back into that window again and start the setup again. Rather than choosing to do the authorization, which you had problems with, this time just choose the option to allow less secure apps.
It should work after that.