There are some special issues when configuring DONATION to send email through a Microsoft email address - anything ending in @hotmail.com, @hotmail.ca, @live.com, @live.ca, @msn.com or @outlook.com. This also applies to email addresses hosted by MS Exchange, like myname@MyOrganization.com.
The reason there are special issues for such email addresses is because Microsoft has started requiring what it considers to be a higher level of security for applications other than the most common email software (like Microsoft Outlook) to send emails from their email addresses.
If you try to configure using a Microsoft email address in the Maintenance ⇒ Email Sending Configuration window, the recommended approach is to choose the Use Microsoft-Specific Authorization radio button in the 2nd window shown in that Help page. (This option was introduced in release #6.22 of DONATION, in October 2024.) See the details for that below.
If instead you use the Use Normal Server Authentication radio button, and the SMTP Server you set up there is "smtp.office365.com" (the current correct one for Microsoft email addresses), you will probably receive a large message box when you click Test or OK the first time, about there being a problem doing this, and recommending Use Microsoft-Specific Authorization. (That won't happen if it's an email address hosted by MS Exchange, on your domain, because the program cannot know whether your domain's email are hosted by MS Exchange.)
This page explains all of these options.
Use Microsoft-Specific Authorization
This option allows you to grant authorization only for DONATION to send emails using your Microsoft email account. It is our recommended option for Microsoft accounts, since choosing Use Normal Server Authentication has increasingly been failing for our users.
If you click the Use Microsoft-Specific Authorization radio button, the window changes to look as follows (using a fake email address):
Clicking Test will give you a message explaining what is about to happen, which is that you will be taken to a Microsoft web page in a web browser to do the authorization, and it tells the steps you will have to follow, which are also explained here.
Unless you only have one Microsoft account, and are already signed into it in your web browser, you will then see a web page prompting you to select the correct Microsoft account corresponding to the email address you entered in the window above.
Click on or enter the desired Microsoft email account, and enter your password for that account, if you are prompted to do so. If you have 2 step verification set on that account, you will be prompted to do that verification, for instance to enter a code that is texted to you.
Next, you will be taken to a page such as the following:
Click Accept. You will then see a page stating that you have granted DONATION permission to send emails via Microsoft, and that you can close that web browser or tab showing that message, and return to DONATION. Do that.
Note: you may or may not see the blue text "unverified" on the page shown above. You can ignore that. As of January 2025, when this feature was first released, we had not yet been successful in verifying ourselves appropriately with Microsoft to make that text go away - they make it very difficult, for some reason! We are working on it. The emailing will work whether or not we are verified!
Return to DONATION (by minimizing the web browser if you didn't close it, or selecting DONATION on the Windows Taskbar). The test email will also have been sent, to the same email address you are configuring, so you can check that you received it.
This is a one-time set up. Once it has been authorized, emailing using this email account should just keep working in DONATION.
If you ever change your Microsoft email password, the authorization you have granted will be invalidated, and you will have to re-do it.
There is also an option to revoke the permission for DONATION to send emails on your behalf, in the Privacy settings in your Microsoft email account. If you do that, you would also have to re-do this authorization.
You can click OK in the window above to close it, once you have successfully completed your test.
Possible Problem with this Process
If you fail to complete any of the steps above - choosing your account, logging in to it if required, and clicking Accept - you will get one or more informative messages.
If the authorization process is not completed within 90 seconds, it will "time out" in DONATION, and you will have to try it again.
Technical Details about Microsoft Authorization
The authorization process retrieves a complex string of characters, called a token, and stores it in your database so that it can be used again without needing to ask you for your Microsoft email password. The token expires after an hour and after that, it gets automatically refreshed by the program the next time you try to email with DONATION.
This way of sending emails using your Microsoft account is done following what is called the Open Authentication protocol version 2 standard, also called OAuth2.
This topic was last edited on Jan 27, 2025