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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! (Most other email services do not insist on such steps, or call 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. Depending on the internal details of the response received from Gmail, it will either offer you an option to Grant Access for Less Secure Apps, or to learn about generating a special application password just for DONATION and using that password in your SMTP settings.
This page explains those two options.
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.
Which of the two options can be used depends entirely on whether or not you have enabled what is called "2-Step Verification" in your Google Security settings for the Gmail account you are using.
Turning on that setting means that every time you log into your Gmail, you will be sent a code, to either a specified cell phone or perhaps a different email address. You then have to enter that code, before you can access Gmail. (If you have an Android phone, the verification may only require answering Yes to a popup on your phone, rather than using a code.)
If you have multiple users of the same Gmail account, you will probably not want to turn on 2-step verification, because they would probably not all have access to the same cell phone or alternate email address to receive those codes, and so this option would not work for them!
Otherwise, while 2-step verification causes some inconvenience, it also improves the security of your Google account.
When 2-step verification is on, only the 2nd option below, using an Application Password, is available. When it is off, only the first option right below this is available. If you have successfully configured your email sending from DONATION using one of the methods below, and then you change whether or not you are using 2-step verification, your current email sending setup will stop working and you will have to configure it using the other method.
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 the simplest solution, and works the most reliably.
Note: As mentioned above, this option is not available if you have what is called "2-Step Verification" turned on. See the next section (on Generating an Application Password) for what to do if that is the case.
Choosing to grant access for less secure apps 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 should end up on a page such as the following:
If you click the slider shown towards 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", to confirm that it was you making that change. It may ask you to click a button and go to a security web page to confirm that it was you making that change. You should get that email, and if it says it is required, 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).
Generating an Application Password
This way of resolving Gmail sending problems allows you to generate a separate password only for use for DONATION.
Note: This method is only available to users who have turned on "2-Step Verification", as explained above.
To generate an application password for DONATION, you need to log in to your Google account, open your account management page and then navigate to the Security page. The link is: https://myaccount.google.com/security.
If you have not turned on the "2-Step Verification" feature yet, you need to first turn it on there, with a link in the "Signing in to Google" section, as follows:
After that setting is done, you will see the "App passwords" option in your Security page, under the same "Signing in to Google" section, as follows:
Click on "App passwords" to enter the page for that. You may need to type in your password again before you get to that page. You will then see the following:
Choose "Other (Custom name)" in the "Select app" drop-down list box, then enter "DONATION" as the application name. After clicking the "Generate" button, Google will generate and show the password.
The password it shows you appears to be four 4-character sections, but there are no actual spaces between the sections! If you copy it out of the window where it is displayed, by highlighting it with your mouse and pressing Ctrl+C (or right-clicking and picking Copy from the popup menu) it will be all one 16-character password.
Store that password somewhere secure (as well as in DONATION!), because Google will only show it on this page this first time. If you don't record it, you won't be able to see it from any page.
Once you have the password, paste it into the Password field on your Email Sending Options window, and use the Test button to confirm that it is working. That is all you need to do. You will not be prompted with 2-step verification when you send emails from DONATION.
If you have both of Software4Nonprofits' programs, DONATION and ACCOUNTS, you can actually use the same application password for both of them. It doesn't matter what name you gave in the window above.
There's also a Google help page at https://support.google.com/accounts/answer/185833?hl=en explaining application passwords in more detail.