How to re-send emails that are stuck in the outbox
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You can see in the Admin > Channels > Email > Outbound Mailboxes, the number of emails that are waiting to be sent.
In most cases there will be an error message inside the case in Red that says "View Last Error" and/or "Dismiss Error". If you dont see these option here is how you can resolve the cases that are stuck in the outbox filter.
1. Go to Admin->Cases->labels and create a label (ie:OutboxError).
2. Go to Admin->Cases->Filters->Outbox and add an ALL condition to the filter that says Labels does not contain OutboxError.
3. Add another ALL condition that says Status <= Resolved.
4. If you want to resend the emails, then in the agent, go to the case that is stuck in the outbox filter. Copy the last response, paste it into a reply in the agent screen and resend it. If you do not wish to resend it, then add the label OutboxError.
NOTE: If you have too many to follow up with one at a time, you may want to consider creating a macro at Admin->Cases->Macro's that says something like "We are sorry about the delay in sending your response. We had some technical difficulties. Our reply is below.".
Then apply this macro using the Bulk Editor.
The cases will be removed from the filter by the step that you took to exclude the OutboxError label from the Outbox filter, and to also not show cases that are either deleted or closed.
If this happens a lot with your outbound email, then consider the below articles that discuss using the free Desk.com SMTP server.
Why Desk.com Mail is Awesome