Can Not Send Mail- what's going on?

Question

Can download mail but can not send mail. With parallels on and xp pro I can easily set up outlook to send and receive mail. But no! The great Apple which is supposed to be easy can not send an email with the same settings. So, back to Windows to do what should be easy on a mac. I think that perhaps the new Safari or something messed this up.

Answer 1

If you'd like to approach the problem as something you don't understand, and also something that can be fixed, then you'll probably be able to set up your email account.
You say you have emails in the Outbox. I'd move them to another folder you create or delete them. In past experience, emails contain header information that includes mail server information, and sometimes they will never send (especially with Outlook Express), even if you get the account to work. You can try sending them again, once you get the account working.
Next, you need to make sure that you are sending the emails from a machine that is connected directly to RoadRunner's network. They may not work as a relay if you connect from another ISP. It's a port 25 problem that is common these days.
Now for the problem. If you are receiving emails properly, then the POP server information is correct. The mail program is designed to set up to some default settings that work with many servers, and during the process it will try to validate the settings you supply. This can take awhile, and can come up with a failure, due to a wrong assumption. Your email program is assuming that the email server requires authentication. This has been a problem with the RoadRunner system for years. Apparently, some windows email clients do not work the same way, go figure. They seem to have their own problems.
Many people have reported successfully setting up an account with RoadRunner, after first making sure they have the right SMTP server address. It can be different for different parts of the country.
After the email account is set up, and is failing to work, people go into the Mail/Preferences/Accounts/Account Information/Outgoing Mail SMTP Server - Click on the dropdown button - Choose "Edit Server List" - Advanced - Change Authentication to "None"
Here is a related thread with stories of success with RoadRunner: http://discussions.apple.com/thread.jspa?messageID=9128382&
After the changes, I'd quit and relaunch Mail. Not required, but good troubleshooting practice. Since there are no emails in the Outgoing Mailbox, create a short message and try to send.
I have different problems with different companies for both Mac's and Windows machines. The ISP always blames the OS, especially Leopard and Vista (since they work with more intelligent/advanced (maybe) settings. Besides the Authentication issue that pops up with some servers, there's also the occasional SSL variation and/or login name (sometimes it's the first part of the email address before the @ and sometimes it's the entire email address). Some ISP's block port 25, some do not. All of these settings can vary with each ISP, and can change on a whim (especially the port 25 problem), with working accounts going dark because of security changes at the ISP. Telephone Tech support at the ISP is often unaware of any changes in their system because they are not in the IT loop at the company and some will just go into "idiot" mode when you mention Macintosh. The first level support people are using a script on the phone, and their job is to make you go away...
I'm afraid the Great Apple, as you referred to them, is not able or hasn't focused on the ability to automatically set up accounts with every ISP. They appear to have made some assumptions that work with most servers. Who know's, next month the settings or assumptions may work, or Apple may update their setup script to make allowances specific to Time Warner, but since this has been a problem for over 3 years, I wouldn't hold my breath.
Google: leopard mail roadrunner problem = about 96,000 hits of all sorts.
Google: vista email roadrunner problem = about 1,410,000 hits of all sorts.
Google: windows xp email roadrunner problem = 243,000 hits of all sorts.
Looks like Apple's getting it's market share of problems with RoadRunner and Time Warner
My own local DSL is from a company named Centurytel. They are on their 4th email server setup in the last 5 years, and have finally contracted it out to a 3rd party company to administer. I just tell all of my clients to get a Gmail account and get over it. Let's see, a multi-billion dollar company who's reputation and income is based on service... free with 7GB storage, Webmail, POP and IMAP access, specific support for all major mail programs including Apple Mail, and alternate ports that get around ISP blocking. It seems that once you enable POP or Imap access in the webmail settings menu, Apple Mail and Vista seem to know the proper settings to use.
I'd setup the free Gmail account that will work with any ISP you use, before you get really attached to an email account with an ISP that could change as often as competitor's marketing allows. Also, my iPhone supports Gmail out of the box