It’s called, wait for it…. “Mail” What about the native app wasn’t cutting it for you?
It’s called, wait for it…. “Mail” What about the native app wasn’t cutting it for you?
I’d verify that all of your account settings are correct. Hopefully you set up GMail to be an IMAP account (instead of POP) so all of your mail automatically remains on the server in case your Mac dies an unfavorable death.
The section you’re most interested in your case is the outgoing mail server.
If you use Gmail and have an iPhone, you should set up Google Sync for it. It’s great because all of your info lives in Google’s cloud. Contacts, email, calendar… no problem if you lose your iPhone or need it replaced. You just set up Google Sync again and like magic, everything’s back on your iPhone.
However, somewhere along the way, Apple introduced a contact group called “On My iPhone.”

I don’t know if it was in iOS 4.0 or in one of the later iOS 3 versions. That doesn’t matter. Where it does matter is when you’re trying to create a new contact from outside the Contacts application. So like if you get a new incoming call and want to create a new contact from that number from the Phone app, the contact ends up in the “On My iPhone” contact group instead of in your GMail-based contacts. If you end up losing your iPhone or need it replaced, these contacts go out the window.
So, what to do?
Change your default contact group.
Your default account will now be Gmail for Contacts

Unfortunately, I don’t know of a way to get contacts that are already in your “On My iPhone” folder up into the GMail contacts. If you figure a way out, let me know.
Outlook 2011 is shipping without Sync Services as the development team could not finish the feature in time to make it work reliably. It will be released in a future update.
If you’re on GMail, a better solution may be to set up Outlook to use GMail and instead of syncing your iPhone to your computer, use ActiveSync to have your iPhone grab your data straight from Google over the air. I use this for my iPhone and it’s awesome.
Almost sounds like you’ve got a port number off or something. Or maybe SSL not enabled when you should. Or, you’ve got SSL setup but using the non-SSL port.
I’d also take a look in Console to see if Mail is throwing any errors in the background.
Apple Mail should delete items properly when using IMAP. One thing you may want to check out is the mailbox behavior in the account settings. Mail may need to be told which folder to treat as Trash so that the IMAP sync properly happens (and so you can empty that trash and have the items actually be deleted on the server).
Tschüss!