SMTP server delays

I just set up an @me.com email address upon installing iOS 5 yesterday (I'd used iTools, .Mac, and MobileMe in the past, but let my account run out). Anyway, I've noticed that if I send an email from my iPhone, or from the iCloud web client, it gets delivered right away. But emails sent via SMTP are delayed indefinitely. Two emails I sent to my other addresses from Outlook 2011 via SMTP, over two hours ago, for example, still have yet to come in.

I'm using smtp.mail.me.com as the outgoing server. SSL, Port 587. I get a certificate error when sending but the message still sends; it's just not delivered in a timely manner.

Anyone else seeing this? Have you tried sending yourself a test message via iCloud SMTP and does it get delivered?