My Email is Stuck in the Outbox

If email is stuck in your Outbox, it could one of several possible issues outlined below.

  1. You do not have permissions to send from the address you are selecting, or you are trying to send a message using a draft created by someone else.
    • The permissions issue must be resolved by your Exchange administrator (we recommend using PoliteMail templates instead of shared drafts).
  2. Your Outlook .ost file has become corrupted.
  3. You are not connected to the PoliteMail Server or your message might be too large to send via the Outbox Server.
    • If you are trying to send through the PoliteMail Server, you may need to check your connection settings and reauthenticate your server. Go to PoliteMail > Server Connection. Verify that Send Email Via: is set to your organization's PoliteMail mail server.
    • You may also want to clear your browser cache. As Outlook currently uses Internet Explorer no matter what browser you use.
  4. Finally, if you are using Outlook 2007, this is most likely related to a known bug in Outlook.  Using the manual sending process below is a good workaround to force stuck messages to send.

How to manually re-send email that is stuck in your Outbox

  1. Click the Outbox folder to view the items in your Outbox
  2. Double-click the items to open them
  3. Switch back to your inbox – this is important, because if you are in your Outbox while you are resending message, they won’t go out
  4. Send each item


  • Just because the item is in your sent items folder, it doesn’t mean it went out. When the item is put into the outbox, Outlook considers it as sent (as does PoliteMail is you are sending tracked email). You can confirm that your message went out by checking in the Results folder.
  • When you click on a message within your outbox, it will never be sent. This means, when you select the outbox folder, and the top message is selected/highlighted by default – it will never go out until you resend it. This is because that mail item will be marked as open, and Outlook will not send open mail items.

Other Possible Reasons

1. Your ISP has send limitations

The most common would be that your Internet Service Provider (ISP) has a daily send limitation. Once you hit this limit, the remaining email will sit in your inbox until the next day, when your ISP will accept more email from you (e.g. Comcast provides internet access with email services, but limits outgoing email to 250 per day, Google Gmail has a 500 per day limit). You can overcome this limitation by sending from the PoliteMail Mail Server instead of your Outbox.

2. You do not have adequate Exchange permissions for this address (typically occurs when using a shared mailbox)

If you do no have permission to send from the email address you are selecting, or do no have permissions to save a draft to a shared mailbox (e.g. a draft created by someone else), or to send from the shared mailbox, the Exchange may not accept the messages from the Outbox. Your Exchange admin may be able to assign the adequate permissions for your account(s).

3. You used the delivery delay or schedule send options

When you use these features, and set a data and time in the future when you want the email to go out, Outlook will place the items into the outbox, but will not release them until after that specific date and time. Note that Outlook must be running in order for such email to go out.

4. Conflicts with other Outlook add-ins

This problem is linked to other Outlook add-ins which use the Outlook Object Model to access the message and inadvertently mark it as read. As Outlook won’t send read messages, it remains in the Outbox until you open the message and resend it. Add-ins that read or access your email as you are sending it are known to potentially cause this issue, such as Business Contact Manager (BCM), Norton Anti-Spam Outlook Plug-in, MS CRM 3.0 Add-in, iTunes Outlook Add-in, Outlook Add-in. You may disable these add-ins or try to install newer versions of these add-ins to prevent the issue.

5. Conflicts with RTF/HTML code

Outlook is very particular about the HTML it can handle. Outlook adds Word compatibility code to the email during the editing process, such as RTF and VML code for it’s display of images or objects that are aligned. It removes some of that code immediately prior to sending the email. If you are forwarding or replying to a long thread that contains images, that alone may introduce enough complexity to cause an issue. If you are using HTML template or importing HTML code that is overly complex or otherwise not compatible with Outlook’s processing, it usually results in the message hanging in the outbox. While we do not have access to the Outlook internals, we believe this is most likely a result of the unexpected/incompatible HTML code causing Outlook’s pre-send RTF/HTML conversion and image handling processes to exit prematurely, leaving the email in an *open* state, and therefore unable to send). For these messages, use the re-send instructions above.