Why am I unable to share web content with Apple Mail Application?

Sometimes when I share via email from a web page, the Apple email opens up and the photo attachement is visible. I can enter the to: address and the subject, the the Send button icon is disabled. Then other times, the send button is enable and I press it but the email never makes it to the destination. Is this a problem with my configuration? What do I need to do? My primary email is with gmail. Sometime the button is enable and I'm not sure what changed and the email appears to get sent, but it never makes it to the destination. In the image below the To: Me is my gmail address. On the left it shows that some emails have been sent, but I don't receive them.