Why Are My Emails Getting Stuck in Drafts When I "Send With Groove"?
Composing a New Message
When using the "Send with Groove" button on a new message, it is possible for the email to seem "stuck" in your Drafts. If you are using the Groove add-in within the Desktop application for Outlook on Windows, you may have a setting enabled called "Cached Exchange Mode". This setting saves a copy of your inbox to your computer in case you want to check your email while you're not connected to the Internet. This setting affects the "Send with Groove" button, because it requires Groove to wait or up to 5 minutes before being sending out your message. Usually the message will send between 0-60 seconds from when you click "Send with Groove" but it can take up to a few minutes in some cases.
If you'd like to avoid this, you can disable Cached Exchange Mode - Details Here.
Replying to a Message
When replying to a message from the Outlook Desktop application on Windows, most of the time your view is in what's called "Inline Reply Mode". This means that the reply box is inline with your Inbox, as opposed to popped out in its own window. In this scenario, when you click "Send with Groove", Outlook's functionality does not let 3rd parties such as Groove to close the email, and move you to the next item in your inbox. Instead, it will look like your email is "stuck" until you navigate away.
In this scenario, you can safely navigate away, and Groove will send your reply out. Alternatively, you can "pop-out" your reply into its own window; after doing so, clicking "Send with Groove" will send your message and close the window for you, similar to a new message.
Why Am I Getting Desktop Notifications When Opening My Own Emails?
Unfortunately, Groove (or other 3rd party applications working in Outlook's application) cannot fully block the self-open notifications. However, you can set up Outlook to prevent these notifications by default. The way to do this is to block images from being automatically downloaded, as shown below: