In general, this is probably because one of, or a combination of the following reasons:
1. Outgoing mail server requires authentication
To avoid abuse by spammers, many outgoing mail servers require authentication for relaying messages across the the internet. You should check if the outgoing mail server you are using for this account requires authentication, and if so properly set it up in your account settings. These typically use the same credentials as the ones for checking your mail with the same provider.
2. Outgoing mail server only accepts connections from the same network
Many ISPs only allow connections from hosts which are connected through their own network. If sending mails through your ISP's outgoing mail server works fine from your home Wifi, but stops working over a cellular data connection, or an external Wifi hotspot, this probably is the case.
In this case you can use another outgoing mail server. If you have a Gmail or an iCloud account you can use those outgoing servers for sending mails.
3. Incorrect settings
Double-check the settings for your outgoing mail server as they are specified by your email provider, especially server name, encryption and the port to connect to. If everything looks ok, try to recreate the account. For AOL and other popular services, there are presets for creating a new account which will fill out all the correct server details.
The specific settings for AOL's outgoing mail server are specified here:
SMTP Outgoing Server Address: smtp.aol.com (Use port 587 for standard or 465 for SSL connections)
SMTP Username: YourUsername@aol.com (or @love.com, @games.com, etc.)
SMTP Password: password you use to login to Mail
For a secure connection, check the SSL option for IMAP/POP and TLS for
SMTP in your mail program.
To make new SMTP:
Open Mail Preferences.
Click on Accounts.
If you have more than one click on one of them.
In that window look for Outgoing Mail server (SMTP).
from the pick up select Edit SMTP server.
In the new window select the (+) and enter a description (name you like), and smtp.gmail.com
Back in Account screen select that name.
Best Answer
I, too, lost my Outbox, but for a different reason.
I composed 15 messages on an airplane and "sent" them, which put them in the 'Outbox'. When I arrived home, I:
I eventually found them in: ~/Library/Mail/V2/Mailboxes/Outbox.mbox/some-UUID-here/Data
By selecting a time that was an hour (or so) before their disappearance, I was able to restore them from my online backup service to a different location (e.g. ~/Desktop/mail_app_message_restore). I'm betting that TimeMachine could do something similar.
The messages were distributed (hashed, actually) among many directories, but when I issued this command from the command line, I found all 15 missing messages:
Notice that the hash directories (e.g. Data/5/4/1) are just the reverse of the top few digits of the message filename. All of mine were in this 5/4/1 directory, but your numbers will be different. It's a big directory structure, but there were only a few messages sprinkled through it.
Best of luck!!! Michael
P.S. Notice the side benefits of automagic backups? What a great feature! I'm so glad that it got a snapshot as soon as I got online, but that there was time before I tried to send them. I think TimeMachine would have been even better about taking offline backups before I reconnected to the network.