Mail app won't let me send mail

Since updating to the newest operating system, my Mail app rarely works. I have three different work accounts set up with it and it only recently started connecting them all again. However, I'm still not able to send any mail at all from any of the accounts and I can't figure out why. I know that the passwords are all correct and I have always been able to send from here. The connection doctor just keeps saying it can't connect to my accounts when I'm trying to send. The purpose of me using the app is so that I don't constantly need to log in and out of different accounts in my browser. Does anyone know how to make this work again?

Similar problem here. The Troubleshooting link from Linc did not help, nor did over two hours on the phone with Apple Support using screen sharing. I have iCloud mail with three addresses: .mac, .me and .icloud. None of them will send. This issue has occurred fitfully for years, across multiple iMacs and Operating Systems. This time it has lasted for a week, forcing me to use iCloud Mail in Safari to send emails.
While talking to Support we tried to Edit the SMTP Server List, creating a new server at smtp.mail.me.com. After plugging in all the appropriate data and saving, it all vanished and reverted to Outgoing Mail Server (SMTP): iCloud (iCloud, Offline). The newly created SMTP server was gone. Two different Support Techs watched this happen multiple times. I have signed out of iCloud and then recreated the account. I have even done a Clean Install of Yosemite, which involved hours and hours and then setting all my Prefs manually so as not to drag in any old, corrupt files. No change. Outgoing email sits in the Outbox folder and periodically pops up an error message saying it can't be sent.
In the past this issue only affected my iMac. Now it is also crippling outgoing mail on my MacBook.
Besides the Clean Install I have: Rebuilt Permissions, Reset PRAM and SMC, repaired Prefs, etc., etc.

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