Dear Jim,
I'm sorry to hear that you cannot create a new session with the in-app support person, I'd like to continue to help you, but to help you better, could you please capture a screenshoot of the details of your account settings in Tools > Accounts and upload
the screenshoot in the forum?
In the meantime, since your Outlook client version is an old version, firstly, please go to the
Help menu and click Check for updates to update your client to the latest version.
Also, may I confirm if you have tried to create a new Outlook profile and add your Shaw account to a new profile to check this issue?
If the issue persists in the new profile, then kindly delete keychain based on the steps below:
- Make sure you quite Outlook and other Office apps, then go to KeyChain Access
- Search "Exchange" under Login --> All Items and delete everything
- Search "Office" and delete everything
- Search "ADAL" and delete everything
- Launch Outlook
- You will get the activation prompt and then If account is already added.
Hope above steps will help to fix this issue for you. However, if the issue persists, I'd like to recommend you login your Shaw account with the web browser to access your emails to work around this issue.