Issues with Sending Bulk Email

Currently schools that use SchoolTool to send bulk email to more than 100 recipients, may experience problems where more than the usual number of recipients do not receive the message, nor is the user whom sent the bulk mail provided any warning or error message on-screen in SchoolTool or later in an email.

That’s because messages sent in bulk to over 100 recipients, can be seen by the well-known email providers (i.e. Google, Hotmail, Yahoo) as SPAM due to the sheer number of messages being “dropped” onto their system at once by your school's mail server, which happens when bulk mail is sent.

Some schools achieved improvements in sending mail to over 100 recipients simply by changing the SMTP Relay Service in Gmail to allow only for secure Transport Layer Security (TLS) Connections as illustrated in this video:

After completing the steps in the video, in order to make the email feature in SchoolTool continue to function, the school will also need to login to SchoolTool and navigate to Maintenance>Application>Network Settings module and modify the "Port" that appears in the "SMTP SERVER PORT" field to 587 as illustrated below:

Schooltool SMTP Settings for GMail with TLS Settings Enabled


Finally, SchoolTool is not currently designed to automatically “chunk” messages sent in bulk to mail providers (e.g. send messages only to groups of 50 at a time), which is generally thought to be the “best practice” when sending messages to multiple recipients (bulk mail), as doing so keeps the potential for those messages to be considered as SPAM much lower.

In response, we have put in a feature request to SchoolTool to ask for an automatic "mail chunking" feature, but in the meantime…schools that wish to send out bulk mail to more than 100 recipients using SchoolTool, must instead take manual steps to “chunk” the recipient list up into smaller quantities (e.g. 50 recipients at a time), so that the sender can be assured that all recipients receive the message.

Unfortunately, using the school's mail server to send out bulk email (even when using Google Mail as your email service) does not 100% guarantee that all recipients will receive the message you intend for them to receive. That’s because the way in which the well-known mail service providers work together to prevent SPAM, involves smaller entities (like your school) that want "guaranteed delivery", to actually pay for the right to ensure that all bulk mail sent is delivered.

The best way for a "small entity" like your school to truly get “guaranteed delivery” on bulk email it sends, is to use a company that the school already pays/contracts with, for the right to guaranteed delivery.

If your school uses one of the following products, you're already paying for "guaranteed delivery" when it comes to sending bulk email:

  • Blackboard ConnectEd or Mass Notify
  • SchoolMessenger

Instead of sending out bulk email messages using SchoolTool, we are suggesting that schools consider using the notification systems they already pay for to send bulk email, as by doing so you are by default...guaranteed that your message will be sent to every recipient you intended it to be sent to.

In addition, using your schools notification system allows you to run reports to easily confirm and verify which of the email addresses that were sent to, are considered bad or invalid, which is something that SchoolTool will not do for you at this time.

If you have additional questions or concerns regarding this article, please send an email to If you'd like to know more about using your school's notification system to send out bulk email messages, send an email to or call our Parent Notification team at 1-800-722-5797 option 2 then option 3.

We're here to help!