A search term that will help folks get to this article:
Can't send email through Outlook with Charter
Hopefully this will save you time. Charter practices port blocking. (see the bottom of this article for possible solutions that may work for you)
There are a lot of good reasons to practice port blocking - it cuts down on spammers, viruses and worms, adware/spyware, etc. The negative side effect is, sometimes it prevents certain services from working. For instance, email services and programs use a port (think of it as a tunnel through a wall) to send email. The normal port they use is 25, so Outlook defaults to that port anytime you set up an email address.
Charter blocks that port to prevent people from spamming through their system. (think of it as a guard at the tunnel) Fine, no problem. But they need to be open about that to their customers.
Three mornings ago I opened my laptop and discovered I couldn't send email. At that time I had no idea what port blocking was so I figured it was a temporary thing. When the problem persisted, I called Charter and over the course of two days, talked to three different "tech support" people. (in quotes to convey irony) They ran down their litany of canned solutions, probably straight from a cheat sheet list.
Even though I explained the problem in detail multiple times, they persisted in pointing their finger at Outlook, my computers and my router. (although ALL of them were afflicted with the same symptom at the same time)
Finally, it occurred to me that perhaps the port was the issue, and that Charter had made some sort of change. A quick internet search answered my question. The odd part, none of their tech support people, even their "supervisor of tech support," (even BIGGER quotes) had adequate knowledge to help me fix the problem. Google did.
This is rookie work from a company who provides a substantial percentage of Americans with internet service. They cost me at least a half-day of work.
Here's a solution that may work for you if you're having the same problem. Navigate accordingly:
Tools>Email Accounts...>View or change existing email accounts. Choose the account you'd like to edit and click "change." Click "more settings," then click the "Advanced" tab. The number next to "Outgoing server (SMTP)" is probably 25. Try changing it to either 587 or 2525. Port 587 worked for my Earthlink account, 2525 for my business accounts.