Hi, firstly, I'm using a new identity in Outlook 14.4.7 and set everything up from scratch, then all my mail downloaded successfully from my Webmail IMAP folders.  However, this was not easy. It took many hours to get it connected, even with chat support w/ my domain host for 2.5 hrs.  I turned out that having the "always use secure password option" checked prevented IMAP from working, even though there were no notifications or error messages. When I unchecked this everything started downloading, and then syncing seemed to work fine. I'm using only Outlook on a desktop Mac, no other clients or devices yet.

But as i started deleting messages from the Inbox in Outlook, I was noticing that some of the messages I deleted (not all) then reappeared in the Inbox, even though I confirmed by going in the Trash folder that I did in fact actually delete them. So i deleted them again, and when i checked the Trash there were 2 copies of those messages.  Sometimes i even get 3 copies of the same message with the same date/time. i responded to this Question here with more details about this problem: http://answers.microsoft.com/en-us/mac/forum/macoffice2011-macoutlook/trashed-message-in-imap-account-reappear-in-inbox/0ec483cb-d1cf-4045-b39f-e3dd97591dfa

At times my mail stops syncing even though i make no changes. I'll be gone for a while come back and no new mail has downloaded, yet there is new mail on the server. I have tried changing all relevant account settings in the advanced tab to no avail.  I have inquired extensively with my domain host and they assure everything is setup properly. At the bottom status bar of the Outlook window, it always says "Connected to [accountname]".  I never witness changes there. To the left of this it usually says "All folders are up to date" even though they are not synced. This used to say "Last Sync at [date+time]" but i havent seen that for a while.  I will see this status message change to "sync pending for this folder" and then go back to "All folders are up to date" but nothing actually syncs. 

If i click on a folder in Outlook other than the Inbox and then back, it will sync to the server. I then see the status change to show "INBOX: downloading" or "uploading", "this folder is up to date", "sync pending for this folder," and then back to "all folders are up to date".  Also, if i click on 'synchronize now' in the contextual drop-down menu for the folder, it is able to sync and new messages are downloaded.

A couple times when i went back n forth between folders like this i received a pop-up window error:  "Mail could not be received at this time. The server for account [accountname] returned the error: "Logon Failure: Unknown username or bad password. Your user name/password or security settings may be incorrect. Would you like to try re-entering your password?" If i select Yes, then i get another pop-up "Microsoft Outlook wants to use your confidential information stored in "InternetAccounts Access Group" in your keychain. Do you want to allow access to this item?" I select "Always Allow", it accepts the login info and I'm back to where i was again.

My Account settings always shows a green dot next to the account name.  Whether i enable/disable these advanced settings i don't notice an improvement in syncing: 

- Sync all IMAP folders every 2 minutes:  started with this unchecked and then checked it - still not syncing on its own.

- Use IMAP Idle if the server supports it:  started with this checked then unchecked it but don't notice a difference. the server does support it.

- Refresh server connection after 29 minutes: started with this unchecked, then checked it, then switched it to 2 min.  I'm not noticing improvements to syncing.

I added IMAP Root Folder: INBOX and it deleted all my IMAP folders then immediately redownloaded them.  When I removed it after not noticing improvements in syncing the same thing happened  This process reset all my column settings (in View -> Column) that i spent a lot of time customizing. thanks Outlook!  It doesn't store these settings for future use?

I have tried to research these Outlook problems figuring that it has to do with my Account settings but cannot find much info about these advanced settings. For ex, these pages:

https://support.office.com/en-ie/article/IMAP-account-server-settings-797ba39f-0cba-4c0e-8dd0-edcb975c90ee (same as the Outlook help file)

http://www.officeformachelp.com/2012/05/how-to-move-your-data-to-a-new-identity/

This part is helpful but doesn't seem to explain the issues i am experiencing: "By default in SP2 IMAP operates as “push mail”. It always has an IMAP IDLE command outstanding against the server and will download new email the moment it arrives on the server. For this reason schedules are no longer needed for IMAP accounts. There is no longer a periodic poll for new mail to schedule. IDLE does not download all new mail the moment it arrives on the server—this only applies to the Inbox and the folder that you are currently viewing. Instead, SP2 now provides a periodic poll, which is why Schedules are no longer needed." 

So what happens when the IMAP Idle preference is unchecked?

I'd like to find more information like this that describes how these advanced settings are supposed to work and what changes can be witnessed.  The Outlook help file is very lacking.

If webmail is open at the same time will this cause problems? And is there a way i can verify i have Outlook SP2?  If i'm using 14.4.7 I assume it would require me to have this before being able to upgrade?

thanks