Yes, I did. It doesn't show up in the logs because, I'm unable to send a message - it goes to the outbox immediately. And this led me to the conclusion below.
And by the way, I did get in touch with Apple Support who went through a number of troubleshooting scripts (including trying to use GMail's mail servers) and ultimately had me reinstall OS X from scratch. None of this worked.
Now this problem of being unable to send mail via my iCloud account, from the Apple Mail client, started only around the end of Feb. What I finally figured was that iCloud mail was using random ports on my machine to invoke its SMTP port. Everytime I would disable the firewall on my router completely, iCloud mail was able to send just fine. Recall that incoming was (and still is) working fine. Anyway, I installed wireshark to ID the ports that were being used when the firewall was down. I set up triggers on my router to open these up, turned on the firewall, but it just isn't working. I will have to play around with wireshark and see if I can figure out what ports need to be opened. Unless you or someone else knows. If I figure it out, I will post it here. Mind you, that I need to figure out not only the source ports that need to access port 587 but also what the real target port is (because I don't think it is just 587 as Apple claims).
By the by, when I asked the Apple Technician (some guy who I was transferred to after 3 other people - the one who asked me to reinstall Yosemite) if there was a way to change the outgoing mail server to use SSL, i.e., turn SSL to "ON", he said no there wasn't and why would one need to secure the traffic to Apple's SMTP server anyway? Seriously?
