Downloading my sent messages as recieved messages

Question

I'm fairly new to Macs...but I seem to be having a problem with mail and entourage. The first problem is that I'm trying to delete a hotmail account on that I have on Mail ( I switched to gmail). Whenever I click "delete account" under settings, the spinning wheel of death comes up and the program freezes. Everytime I have to force quit.
The second problem is fairly simple. I downloaded my messages from my gmail account into entourage and mail--it considers all the messages that I've sent in the gmail account as messages that I've recieved. I'm very confused, any ideas on how to fix either problem?
-Thanks alot for any advice.

Answer 1

How did you set up the Hotmail account in Mail? Mail is a standard POP & IMAP mail client. It knows nothing about Hotmail accounts. Setting up in Mail a Hotmail account that doesn’t allow POP access can only be done installing a plug-in that provides support for that type of accounts. If you have problems managing your Hotmail account in Mail, it’s almost certainly because of a problem with that plug-in. You may try reinstalling the latest version of the plug-in if you have an older version (and uninstall it when done):
http://www.automagic-software.com/downloads.php
As to Gmail, well, it does allow POP access but doesn’t work like a normal POP mail server would either. Here are some of its idiosyncrasies:
1. Messages downloaded by any conventional POP mail client are marked as downloaded at the server (but not as read on the web), and no longer available to either the same or any other POP mail client.
2. To make already downloaded Gmail messages available for POP access again, you must go to Gmail’s Settings > Forwarding and POP page, select Enable POP for all mail, and click Save Changes, which will cause everything (and I mean everything) still there to be downloaded again. Alternatively, if you only want to download the last 30 days of mail, you can configure Mail in “recent mode” as described in How should I use POP on mobile or multiple devices?.
3. The Mail > Preferences > Accounts > Advanced > Remove copy from server settings have absolutely no effect on the messages stored on Gmail’s server. Gmail ignores any requests to delete messages from the server made by a POP client. What happens to the messages on the server after a POP client has downloaded them is determined by the corresponding Gmail’s setting alone.
4. Messages created and sent using the web interface will be downloaded by your POP mail client as if they were incoming messages. Although this may seem weird, it's good because it allows archiving all messages locally in Mail, regardless of how they were sent -- as long as you don't access the same Gmail account with more than one POP mail client, that is. You can set up a rule in Mail to automatically route those messages to the appropriate Sent mailbox (or to any other mailbox for that matter) if that's what you want.
5. Messages created and sent using a POP mail client such as Mail are also treated as if they were incoming messages for POP purposes, just as in 4. What prevents them from being downloaded is that Gmail marks them as already downloaded immediately. They would, however, be downloaded if Gmail settings were changed as described in 2 above.
6. As a particular case of 5, messages sent to yourself will appear in your Inbox on the web, but cannot be downloaded by either the same or any other POP mail client without proceeding as described in 2.