Email Sending Configuration

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Email Sending Configuration

The DONATION program can be configured to send emails from various parts of the program, such as with the Database Email Backup menu option, or when you right-click on a filled-in Email Address field for a Donor and pick Send Email from the popup menu, or for emailing receipts.


However, for those program features to work, you have to have first configured the email sending settings (also known as SMTP configuration) with Maintenance ⇒ Email Sending Configuration. (Note: Some other email sending from the program, such as for requesting a license key or an evaluation extension key, do not require this configuration, to make them easier to use.)


When you run Maintenance ⇒ Email Sending Configuration for the first time, the following window will come up:




Where it shows "Microsoft Outlook" under the first radio button above, it will show the name of your default email program, if you have one. If you do have a default email program (other than web mail such as Hotmail, Gmail or Yahoo Mail), from which you are able to send emails successfully, just leave that first radio button selected and click OK to proceed to the next step of the configuration. This option is the most likely to give you correct results, with the least effort on your part.


If you don't have an email program configured, that first radio button will be disabled and the second one will instead be preselected. The DONATION program knows what the email sending settings are for about 50 common ISPs (Internet Service Providers) and web mail solutions such as Hotmail and Gmail. To see whether yours is included in this list, just enter your email address in the field under the radio button for "Determine it from known settings ...", and click OK. If it knows how to configure your email sending based on your email address, it will go on to the next window. Otherwise, it will give you a message saying it doesn't know how to do that. (In some cases, there are multiple setup options for your ISP, and the program will offer to take you to a page on the ISP's web site to determine the correct settings. This currently applies to and email addresses.)


Note: We also have a web page listing the most up-to-date knowledge we have of the settings that work for many common Internet Service Providers who supply email addresses, which you can see here. This is the same information used in this option in this window for "Determine it from known settings ...", although the web page may be more up to date if we have learned newer information and either we haven't released an update including that information yet, or you haven't upgraded your program recently.


Your final option, if neither of those previous choices worked, is to select the third radio button, which requires you to know your own email sending settings. You may need to refer to any documentation you received from your ISP, look up the information on their web site, or contact their technical support department, to get their SMTP settings. After selecting that radio button, click OK.


After clicking OK to any of the above options, or if you have configured your email settings successfully before, the following window will come up:




This specific data has been filled in for our own business email address, but it may be empty or almost empty depending on your settings in the first window.


Note that the Password field will never actually be filled in the first time you come into this window. That's because DONATION can't read your email authentication password from any of the email programs like Outlook, because they are encrypted. Be sure to fill this in, with the email password associated with your email address.


The following is a quick description of each field on this window:


Use Normal Server Authentication or Use Gmail-Specific Authorization: You will always pick the first option, unless you are configuring this with Gmail email address, or you are using Google Workspace (formerly called G Suite) to have your organization's domain email addresses actually be Gmail addresses.That second case, of Gmail addresses or Google Workspace addresses on your domain, is covered more fully in the Help topic Gmail Configuration.

From Name: The name that should show as who the email is being sent from.

From Email: The email address that the email is being sent from.

SMTP Server: The name of your ISP's computer used to send emails

Port: The TCP/IP port number used to send emails. The three most common settings (25, 465, and 587) are on a drop-down list, but you can also type in other settings.

Authenticate: Some ISPs require you to identify yourself with a username and a password before they will let you send emails. Check this checkbox if your ISP requires authentication. If this is checked, both the Username and Password fields must be filled in.

Username: If Authenticate is checked, fill in the username used for authentication. Most commonly this is your email address, but sometimes it is only the first part of your email address (the part prior to the "@" sign) and rarely it is something else entirely.

Password: If Authenticate is checked, fill in the email password used for authentication. You must enter this - DONATION cannot figure it out for you!

Make password visible, rather than stars: If you want to be sure you are entering your password correctly, you can check this checkbox so that you can see the password, rather than just stars or circles in the place of each character.

Security: Some ISPs require some form of secure connection to be made in order to send emails. The three real options are None, TLS and SSL. (SSL is almost always associated with Port 465.) The "Try TLS" option corresponds to the settings in some email programs, and means to try using TLS security, and if that fails, use no security ("None").


Once you have the settings the way you want them, click Test and it will test whether the settings work, by sending you a test email. If it works, the settings will also be saved (as if you had clicked OK, though the window stays open). If it doesn't work, you are given an option to view a log file of the attempt, showing the error, in a window. If that happens, what you will see in that window may seem fairly "techie", but if you look over it carefully, you may be able to figure out the problem. (The most common problem is not filling in the email Password field, or not correcting it after you change that password.) Alternatively, contact your ISP for assistance with the required SMTP settings. If necessary, you can email us the contents of that log file for our advice, with the Email to Software4Nonprofits button on the window that is displaying it.


One small point is that if you have "Try TLS" under Security, when you do a Test it will figure out whether you do need TLS or not, and change the security setting to either None or TLS. Assuming that the test was successful, leave the changed setting the way you see it.


Once you have done a successful Test, click OK to close the window and save any further changes. You can of course also click Cancel if you want to abandon your changes, or Help to read this help page.


Possible Common Problems


The most common problem is always just having the wrong email password listed, including if you have changed it recently online but did not yet change it here. Please try re-entering that and clicking Test again before you contact us for support.


Some email services offer an optional two-step verification system (also called two-factor authentication) before you can send email, where you require both a password and something else, like a code obtained using your phone.


For Gmail, there are several cases, depending on whether you want to configure it with all of the settings shown in the window above, or switch to the Use Gmail-Specific Authorization option. All of the issues are fully explained in the Gmail Configuration page.


For Apple email addresses ( and, if you have two-step verification turned on, you have to create and use what they call an app-specific password in DONATION. Details of the relevant links on their support website are here.


For Microsoft email addresses (,,,,, and, if you have two-step verification turned on (or perhaps in some cases even if you do not), you have to create and use what they call an app password in DONATION. Details of the relevant links on their support website are here. Also, Microsoft email accounts allow a maximum of 300 emails sent per day, in some cases less for newer accounts or ones they do not consider to have established a good "reputation".


For other email services, they may have similar options for if you have two-step verification turned on - please let us know the details if you figure them out and we will add them here and online! Otherwise, you may not be able to configure the email sending in DONATION to work if you have this turned on, so you may have to turn it off (at least temporarily) when you wish to send emails from within DONATION.


AOL email addresses apparently always require you to create and use what they call an app password in DONATION. Details of the relevant links on their support website are here.


Rogers email addresses apparently also always require a special app password - details of where to go on their support site to learn how to do this are here.


Yahoo email addresses may also always require a special app password - details of where to go on their support site to learn how to do this are here. Yahoo allows a maximum of 500 emails sent per day through your account.


Specific Gmail Problems


There are known issues when using Gmail, when trying to send email through it from programs like DONATION that it doesn’t know about. See Gmail Configuration for an explanation and the process to resolve this, which has three variations depending on which of the radio buttons you choose at the top of the window, and whether or not two-step verification is turned on.


Firewall Issues if your Test Fails


One possibility if your test fails is that your firewall is blocking your outgoing access on port 25 (possibly except for your regular email program), or on whichever port you are using. If that is the problem, you will get an error message suggesting this as one possibility, and the log file it offers to show you will include lines such as any of the following:


socket is not ready for writing

Connect function failed.

WSAEWOULDBLOCK The socket would block.

failedWaitToConnect: Socket operation timeout.


If that is what you are seeing, and you have carefully checked all of the settings in the window, try temporarily disabling your firewall, and doing the Test again. If it works now, that is clearly the problem. You will then want to consult your Firewall's Help to determine how to either allow outgoing port 25 (or whichever port you are using) from all programs, or at least how to allow it from donation.exe.


Don't forget to re-enable your firewall overall after this test. It is not very safe to run a computer without a firewall these days!


If you have Multiple Databases


If you have multiple databases and are switching between them, it's actually possible to have different email setups for different databases. When you first try to use an email configuration in a new database, or one that you haven't specifically configured email in yet, it will start with the configuration from a previous database, but you can change it if you wish.


Redoing Your Configuration from Scratch


If you have configured your email settings once, but don't like the results, and want to start over from the first window above, there is a trick. (Normally, once it has been configured once, Maintenance ⇒ Email Sending Configuration takes you straight to the second window above.) The trick is to delete the contents of the SMTP Server field and replace it by "NONE" (without the quotes), and click OK. Then use Maintenance ⇒ Email Sending Configuration again, and it will take you to the first window. (If it has "NONE" in the SMTP Server, it figures you haven't configured anything successfully yet!)

This topic was last edited on Feb 17, 2023