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There are some special issues when configuring DONATION 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 DONATION 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 the 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 DONATION.
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 DONATION. This is definitely the simplest solution, and works the most reliably.
Clicking the Grant Access for Less Secure Apps button 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 DONATION, 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 DONATION 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.
While this option is arguably more secure than the Grant Access for Less Secure Apps option, in our experience it is also a bit more flaky.
If you click the Authorize DONATION button, it will take you to a page in a web browser (embedded in a window from DONATION). 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 DONATION 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 this all Doesn't Work, or Stops Working?
Occasionally these methods don't work, or stop working.
As mentioned just above, one solution may be to change your Gmail password, which undoes your authorization setup, and will allow you to do it again. However, of course that will also affect any other program you use to access your Gmail!
Another thing you can try is redoing the email configuration in DONATION from scratch. Instructions for that are in the Configuring Email Sending Help page here. Some users have found that doing that either immediately allows whatever you have done here before to start working, or allows you to do one of the above two options again, and have it work.