Hi all,

A problem that has been around in Outlook since 2010 (and possibly even 2007): any sent emails that are queued in the Outbox and then selected (but not opened) will never get sent.

After sending an email it goes to the Outbox which will contain all currently unsent emails queued for sending in the next Send/Receive operation.

If you then switch the folder view to the Outbox, Outlook will highlight the first of these emails by default. The appearance of the email will then change from bold/italic to bold only, and the email will NOT be sent (ever). All other emails will be sent during the next Send/Receive as long as they have not been selected. Once outbound emails are in this state, they cannot be sent - if you open the email and click "Send", it remains in the Outbox in bold (but not italic) and will not be sent during the next Send/Receive. The only way to send is to Open, Reply (All), then send as a new email. The new email will be in the Outbox in bold/italic and will send during the next Send/Receive.

I have seen this behaviour on multiple installations across multiple ISPs and it's a constant source of frustration.

Any solutions?

Thanks in advance! 

Chris

Does it happen in Outlook safe mode without preview pane/reading? Some add-ins may call the message in outbox folderand lock it.

Type "Outlook.exe /safe" to launch Outlook and then turn off the Reading Pane from View Tab > Layout section.

In general, we don't suggest user to check the message in outbox folder. If you need to look at the items that are waiting, use Find or Advanced Find, or create a Search Folder (but don't preview messages in the Reading Pane) and include the Outbox folder in the search.

Tony Chen
TechNet Community Support

• Marked as answer by Max MengMicrosoft contingent staff, Moderator Tuesday, June 25, 2013 7:23 AM

Hi Chris

The emails that is stuck in the outbox, right click them and move them to the inbox.

Go to your inbox, open the email and send it, it will successfully send without having to Reply to All.

Question, why does the email get queued up in your outbox? Is it because of the size of message or do you compose and send emails when you are offline?

Change your send and receive settings to every 30 seconds rather, but normally when you send it should not queue it should execute to send it immediately to clear the outbox.

Let me know if moving to the inbox helps tho.

• Marked as answer by Max MengMicrosoft contingent staff, Moderator Tuesday, June 25, 2013 7:23 AM

FWIW, this last solution did not work for me. I keep my mail set to send every 30 minutes, even when I'm online. This gives me the chance to fix typos, add changes, or retract anything that might be inflammatory before I send it.

I have been using Outlook forever, with Outlook 2010 on Windows 7 Pro 64 up through March of this year. Since March, I upgraded to Outlook 2013 on Windows 8.1 Pro 64. The send every 30 minutes has not been working (I realize that's a separate thread - I'm only mentioning it here because you mention it in your solution).

However, what started happening yesterday is that certain messages will not send. I cannot find the pattern to what is not sending. The message are not large. They include text only and HTML messages, with and without attachments. They include messages created from New Message, and Forwarded messages (have not yet had this problem with a Reply). I am able to send other messages (in the same Outbox at the same time) to the same recipients, but certain messages will not send.

I never realized that opening messages in the Outbox was a discouraged practice - have been doing it literally for years if not over a decade. However, the symptom I'm noticing is that the message is being created in the suspended state. That is, if I write a normal message, it goes in the Outbox and is listed in blue bold italic until it Sends. If I open it and save it, it changes to black, unbold, roman font and will not send. If I open it again, and click Send, it will behave as it should.

What I am seeing now is that the messages are being created as black, unbold, roman. If I open the message and click Send, it flashes briefly, but the status doesn't change and it still will not send. I tried the Inbox option and it did not work.

The Reply All solution, however, does work. It creates a second copy (blue bold italic) in my Outbox which sends as it should. I have tried this with the 3 problem messages I've had in the last 24 hours (out of maybe 2-3 dozen) and it has worked each time.