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.
I did a little digging and found out a little of what OSX tries to do to auto-configure an email account.
In system preferences when adding a mail account, OSX makes a POST to https://mac-services.apple.com/iconfig/dconf the post parameters are:
domain: EMAIL_DOMAIN_THE_USER_ENTERED.com
version: 1
capabilities: MACOSX
For a service like gmail the following is returned:
<domain>
<name>gmail.com</name>
<description>Gmail</description>
<service>
<hostname>imap.gmail.com</hostname>
<port>993</port>
<protocol>IMAP</protocol>
<ssl/>
<requires>MACOSX</requires>
<authentication>PLAIN</authentication>
</service>
<service>
<hostname>smtp.gmail.com</hostname>
<port>587</port>
<protocol>SMTP</protocol>
<ssl/>
<requires>MACOSX</requires>
<authentication>PLAIN</authentication>
<usernameIncludesDomain/>
</service>
</domain>
Unfortunately, for my domain I receive the following response:
<domain>
<name>EMAIL_DOMAIN_THE_USER_ENTERED.com</name>
<unknown/>
</domain>
As far as I can tell after an unknown response OSX gives up and requires a user to enter the details manually. Capturing network packets I see no attempt by OSX to fallback to using SRV DNS records, or the Exchange Autodiscover.xml mechanism.
If I get a chance I will open a support ticket with apple to see how one gets added to their mac-services list.
Best Answer
Grayed out Quit in Mail usually indicates that mail is busy doing something (like sync) and does not allow quitting.
Here are few steps you can do:
1- Run the Connection doctor
2- Enable the Activity window to see what is going on (get mail)
3- Delete that account and recreate it. (no worry, your email should be on the original server (ie gmail), but better check that before.
4- Wait for it to complete its duty. (like updating 10000 emails)