TexasCHLforum.com

It sounds like roadrunner may have changed their policy on the way mail gets sent. I know they tend to be annoying when it comes to IMAP/SMTP settings. My guess is that your account settings in outlook are set as send-after-receive, which is a way you can send email without passing login credentials by using them on the receive portion first. My best guess is that roadrunner disabled that, causing outlook to ask you for your password now that it gets asked. I'd go into the account settings and check your send mail settings. You may also want to contact roadrunner directly, as much of the documentation floating around online may be outdated.