If email is stuck in your Outbox, it could one of several possible issues outlined below. However, if you are using Outlook 2007, it is most likely related to a known bug in Outlook 2007.

In Outlook 2007, there is a *stuck in Outbox* bug, documented all over the internet.  PoliteMail runs into, it seems to be related to HTML formatting, but we have not been able to isolate it.

Three things usually help resolve this however:

  1. Run the latest sp3 version of Outlook2007  – download update here
  2. Use the PoliteMail > Process Outbox feature
    This is a work-around we developed to help overcome the Outlook bug, and will force the messages out of the Outbox to be sent.
  3. Once you are running the latest Outlook 2007 version, or Outlook 2010, then repair your Outlook data file.

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. If you send the email track, the make sure 1to1 with Tracking is unchecked before you re-send (it’s already been tracked)
5. Send each item.

Important Note:  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).

Another Important Note: 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.


How to send via the PoliteMail Mail Server, instead of the Outbox:

1. Use the PoliteMail menu at the top of your Inbox, PoliteMail > Connection Settings

2. Click the PoliteMail Server tab

3. Change the Send Email Via: to PoliteMail mail server


Below are the other reasons you email may be stuck in your Outbox:

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 (see page 5).

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, Salesforce.com 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 templaate 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.