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Right, I get all that. I'm saying you just have too many hops. Why aren't you using gmail for domains and just having your devices pull from that directly, rather than doing this forwarding? http://smarterware.org/3628/host-your-domain-email-at-gmail-without-forwarding

I'm not sure why you have iCloud involved at all. can you explain that part of it? Just set up mail to send and receive from your domain, done. Don't even involve iCloud.

He said in the OP that IMAP and iCloud were not playing well together. I asked him why he was using iCloud at all, you replied because of folders, I noted the issue with Gmail and folders, which is what IMAP support was intended to allow, but it's wonky. So I don't know if his answers would be...

OK, but how does that help Dave with his issue? You've hacked together something that will work for you but he's stated that it's either not working or too complicated for him to do the round tripping that you are. Wouldn't it be easier for him to move to a different email provider that works...

Folders, ugh. Folders are the root of all evil with Gmail. I understand why people do it. I understand why gmail won't. You can either do it Google's way and live a problem free life, or you can try to make it do what you want it to do, which it is not designed to do, and go batshit insane...