I finally convinced my best friend to enter the 21st century by purchasing a laptop. She is the proud owner of an HP Mini Notebook, very cool, even though it is a PC (I'm a Mac Snob). Inevitably I created an internet/email Frankenstein and have become her very own 24/7 tech support, which brings me to the purpose of this post.
My friend signed up for an AOL email address and I set-up her Outlook Express with POP3 settings. All was working fine. After a few days, even though emails sent in Outlook appeared sent, they were not reaching their destination. What made me crazy as I tried to troubleshoot the problem was why it worked sometimes and didn't others. All settings in Outlook were correct and test messages were sent but not received. OK, I signed on directly to AOL and tried to send an email from her account, this "image challenge" popped up to verify that I was a human and not a computer. I enter the required code and voila, her emails immediately can be sent and are received within AOL and from Outlook. The bottom line here is that Outlook is not equipped to deal with the image challenge, it has to be done within AOL. Awesome! I'm brilliant. Or so I thought, until a few days later, when the same problem manifests. Ultimately, after much frustration, I figure out that this "image challenge" AOL has engaged has some sort of a re-set timer and has to be fed regularly. Unfortunately, I haven't figured out the pattern nor do I want to spend the time trying to. It is easier for my friend to blow off AOL email and use Gmail, which at this time doesn't have this obnoxious challenge.
If you have experienced the same baffled frustration using Outlook with your AOL email, I hope this helped. You and your Outlook are working just fine, it is AOL creating the problem. If you are attached to AOL, don't use Outlook, sign in to AOL and do your business within their world so when the image challenge pops up you can feed it. Good Luck!