I can't send newsletters from Sharepoint, but I can send a link to the newsletter. What's going on?

I have been having an odd issue with Sharepoint's newsletter feature.

When I create a newsletter, it appears to post correctly to our intranet site and everything. I would then like to send out the newsletter as an email to my colleagues so they can read it directly in their email. To do this, I attempt to enter my individual email in the 'to:' box. The 'Send' button changes color and I am able to click it and receive an 'Email Sent' confirmation notification, but the email never arrives in my inbox.

The strange thing is, when I take the same steps but add the step of checking the 'send as a link' option before I send the newsletter to myself (therefore foiling my intent to send the newsletter directly in the email), the link does arrive in my inbox.

Obviously I have something like a solution here, but I can't imagine why I would receive the link version of the newsletter and not the newsletter itself through the same process. I want to reduce one step for my coworkers in reading the newsletter, so that they don't have to log in to Sharepoint to read it if they don't want to, especially for those that might be reading it on a mobile device.

Is this something I need to talk to my IT team about or is this a known bug in Sharepoint's newsletter feature?