Outlook Message Stuck In Outbox: Troubleshooting Steps!

“Every time I try to send email with large attachment, the Outlook message stuck in Outbox and then I have to send it through my Gmail account. I think it is a drawback of this email client that a message of large size cannot be sent through it.
If you are amongst those who think that it is a pullback point of Outlook, then it’s absolutely incorrect. Sending an email with large attachments is possible with Outlook; all that is needed is changes in default settings of the application. In this segment, we will have a discussion on how to delete message from Outlook outbox and what measures can help you in sending large message without hindrance.
There are some techniques that can be adopted to delete a stuck message in outbox. Here is the simplest method shared:
a)    Run Outlook in offline mode (This will disconnect you from Server)
For Outlook 2007: In the File menu, drop down to Offline.
For Outlook 2010/2013: In Send/Receive tab, click on Preferences and then Work Offline button
b)    Delete the message from outbox and Close Outlook. Open Task Manager (CTRL+SHIFT+DEL) and check out if any instance of Outlook is running at the backend. In the Processes tab in the task manager, check that outlook.exe is not enlisted. Open Outlook again.
Now, this is what you did to cope up with the problem right? What if you again get into such troublesome situations where large outgoing email stuck in Outlook outbox folder. To work around the problem, the solution is to increase the Server time in the email client. Before moving on, let me explain what actually this Server time out is and how does it affect message sending in MS Outlook. 
What is Server Time Out
MS Outlook (along with other IMAP or POP3 mail clients like Outlook Express) uses the Server time-out technique. It is the time period that specifies how long Outlook should wait for sending or receiving a message from Server. If this time passes and no response from the Server has been availed, the connection is considered to be LOST.
By default Server time-out is 1 minute which is very less. In scenarios where internet is slow or there is large attachment in message, the time taken in sending/receiving an email is high and if Server time-out is 1 minute, then Outlook re-submits the message for next send/receive interval. So, the point here is Outlook time-out should be increased up to 5 minutes in order to avoid Outlook email send/receive failures. 
How to Increase Server Timeout in Outlook:
Outlook 2000:
  • Open Outlook and from the Tools menu, select Accounts.
  • Select the Account and click the Properties tab.
  • In the Advanced tab, increase the Server time-out.
Outlook 2002/2003:
  • Open Outlook and in Tools menu, select E-mail Accounts.
  • Click on View or Change existing mail accounts and hit the Next button.
  • Choose the account and click Change. Click on More Settings button.
  • In the Advanced tab, increase Server time-out. 
Outlook 2007:
  • Open Outlook and from the Tools menu (Outlook 2007) and move down to Account Settings
  • Choose the account and click on Change. Hit the More Settings button.
  • In the Advanced tab, increase value for Server time-out. 
Outlook 2010/2013:
  •          Open Outlook and in File menu, click Info.
  •          In the Account Settings, choose the account and click Change.
  •          Click in More Settings button and in the Advanced tab and increase Server timeout value.
     Using these measures, you can prevent large outgoing email stuck in Outlook in future. Hope this proves helpful J

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