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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 an option to Grant Access for Less Secure Apps.
This page explains that option.
Note: In releases prior to number 4.13, there used to be another option, Authorize DONATION, which allowed you to give just a specific authorization to Google for DONATION to send emails. We no longer support that option, because Google recently added a lot of complex criteria to allow software companies to do that, which unfortunately seemed prohibitively complicated for Software4Nonprofits to satisfy.
Grant Access for Less Secure Apps
This 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.
Choosing to do this from the prompts that come up 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 slider shown in the bottom right of the image above, it will immediately turn that on. You can then close that window.
Google will likely then immediately send you an email with the Subject "Critical security alert", asking you to click through (using a Check Activity button) and confirm that it was you making that change. You will probably have to get that email, click that button, and answer Yes on the web page that comes up, before sending email will work.
Back in DONATION after doing that, you can 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).