Two unrelated questions, syncing and mail

I have two unrelated questions.
1. I can't seem to for the life of me copy playlists between devices. Both my IPod Nano and my IPhone 4s are connected to my computer right now. Using autofill, I was able to put all the music in my ITunes library on my phone, but when I sellect the playlists, copy and paste them, they won't move and remain only on the IPod and the computer. Can someone please tell me how to get them onto my phone? There are currently no playlists on the phone.
2. My other question is about mail, whenever I send a mail, the phone says that it was rejected by the server and a copy has been placed in my outbox. What's going on here?

1) Is the "Manually Manage Music and Videos" box checked under the Summary tab in iTunes on each of your devices?
2) Try deleting the account under Settings > Mail, Contacts, Calendars, and then re-add it.

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