If you are receiving an error "Trying to Connect", try to send a test email to see if it will go through anyway. This has occurred with several users, as Outlook will display "trying to connect", but it is actually connected. Check Sent emails to see if your test has gone through. If it will still not send your email, proceed below:
TIP for Microsoft Outlook Desktop Users. If you are experiencing issues, you may be in need of an update to your application. Microsoft pushes out updates through the web portal that need to be manually applied to keep your application functioning properly. To check and update your Outlook:
STEP 2: Navigate to Gear Symbol > Office 365 Settings
STEP 3: Click on Software
STEP 4: Desktop Setup > Set up
STEP 5 : Download/ run if it states that you have updates that are needed (you will be prompted to enter in your user creds again)
You may or may not have any updates that need to be applied. You will need to be an administrator on your computer to apply these updates. If you discover that you need to be updated and do not have the authorization to do so please contact email@example.com.