Emails won't send or stuck in Outlook Desired Outcome Emails won't send or giving you fail message Emails getting stuck in your outbox Emails that you are sending aren't being received Step-by-Step Guide If you are having issues sending or receiving emails, try the steps below. Troubleshooting Steps Check your internet connection. Try a different network to test if this is the issue. Close and reopen Outlook to re-sync your mailboxes. Make sure you're connected to the internet. Check your wi-fi, ethernet and network connections. Check if your Outlook is disconnected. You will know it is if at the bottom it shows disconnected, working offline or trying to connect, which will mean Outlook can't reach the email server to send your mail.Try resolving this by clicking Outlook > Work Offline to toggle between offline mode and online mode. You may need to open the message and send it again, or choose Send/Receive. Make sure there's no large attachments. If you have pictures or documents larger than 5MB, delete the attachment and attach a smaller file, seperate the files in different emails, or send a link to the files. If you've changed your password recently, it might not have synced to your Outlook. Click Outlook > Preferences > Accounts and re input your password.