A few facts:

1. It is not my company's policy to require VPN to access email.

2. On my Mac I can only access email when using VPN.

3. My Android phone has no problem receiving email and has become my primary email retrieval method.

4. Whether I am on ethernet in the office (no VPN) or on VPN from home or a hotel/cafe, I am constantly switched into "Not Connected" status.

5. When I am having problems I regularly get prompted for my password (even though I have saved it in my Keychain) and it NEVER works.

6. When I relaunch Outlook and am NOT prompted for my password, it connects and syncs fine.

This point deserves reiterating: When Outlook prompts for a password, it fails to connect 100% of the time and will always fail until relaunched. When Outlook is launched and successfully connects it does so without prompting for a password 100% of the time. This means the algorithm that decides whether or not to prompt for a password is fatally flawed.

7. I have used Charles Proxy[1] to log HTTP traffic and it is a complete mess.

7a. My email ends in @coxin.com, however, while at this company I have had @ajc.com and @cmgdigital.com email addresses and I still receive email that is sent to those addresses in my current account.

7a. I have seen Outlook request https://autodiscover.coxinc.com/autodiscover/autodiscover.xml and get an XML response that includes: <RedirectAddr>[name-hidden]@ajc.com</RedirectAddr>

7b. There is no autodiscover.ajc.com

When Outlook silently switches to "Not Connected" status I can find no way to get it to attempt to reconnect other than to quit and reopen Outlook. Everyone I know says that their iPhones/iPads and Android phones/tablets are the most reliable way to interact with an Exchange server. This should not be. There should be a lot of work invested in connection error handling, messaging, and logging.

[1] http://www.charlesproxy.com/