My Drupal Installation is failing to send some emails and I’m not sure how to fix it.

I’m attempting to setup Drupal User Registration with Administrator Approval. I have a couple of rules.

Event: After Saving a New User Account
Condition: User is Blocked
Actions:
Send Mail – To: example@example.com – A new user has been added, please log in to approve
Send Account Email – Parameter: Account:[account], E-mail Type: Welcome (awaiting approval)

The first email is being sent successfully while the 2nd email is not. Additionally, I have a 2nd Rule for when the account is activated that is also not sending an email to the User being changed.

All instances of emails show up in the log like so:
Email successfully sent to Admin:
MESSAGE Successfully sent email to example@example.com

Email on account creation:
MESSAGE Welcome (awaiting approval) e-mail sent to example@gmail.com.

Email on account activation:
MESSAGE Account activation e-mail sent to example@gmail.com.

I also tried using the same email as the Admin to send it and received:
MESSAGE Account activation e-mail sent to example@example.com.

The only thing I can see that is common and possible screwing it up, is the first successful email does not have a . following the email address while the three unsuccessful emails do.