I'm actually writing this on behalf of the owner of the company I work for.
This morning he was sending quite a few emails from his AOL account, most went except 1, even though webmail indicated it was sent. When we went back to check, the mail was not in his sent items. He tried to send the mail again on a second computer, but the same problem occured.
I did some troubleshooting and found the following:
1. The emails he sent were to 2 people. Both recipient addresses are in the "To" box with proper delimiters between them for seperation. The first email was in the form of email@example.com, the second was firstname.lastname@example.org. AOL Webmail twice told him these emails were sent, but they didn't get to their recipients, nor did they appear in his sent items. I tried sending 2 test mails in the same format, both with the same effect.
2. I sent more test emails to myself and another address, both in the "To" box. The emails were received successfully and appeared in his sent items.
3. I sent a test email to the original 2 recipients, except this time I put the first address into the "To" box and the second into the "CC" box. The emails appeared in his Sent Items, and I assume were recieved successfully because of this.
4. There are other emails in his Sent Items with multiple addresses in the "To" box, and the first address listed in those emails is the first address in the problem emails this morning (I thought it might be a formatting issue with all the fullstops in the email address, but it must not be)
So why can he not send emails to these two people when they are both in the "To" box? Where are the emails gone when AOL said they were sent, but they didn't actually appear in the sent items or in the recipients mailboxes?
Thanks for taking the time to read all that, if you need any more info, please let me know.