Large emails get stuck in Outlook outbox

When sending a large e-mail file in Win 7 Outlook, typically a large mp3 file, Outlook will sometimes get hung up and the e-mail will not leave the outbox. It stays stuck there trying to send repeatedly but never successfully, messing up everything else in Outlook. I have done lots of on-line homework and there are many more suggested simple solutions, but this is the only one that seems to get the job done: Delete a Message Stuck in the Outbox


It's a real pain! It took me about four hours to find the solution that works and then at least 30 minutes every time I have to research the article and then hack Outlook to free up the stuck email in the outbox. The MS corporate on-line forum teckies insist that it is a e-mail client server problem, which is absolutely false as many others also agree. I don't care if the e-mail does not get through as much as I just want to be able to delete it from the outbox when it gets hung up in a never ending loop of trying to send perpetually, eating up processing power, and it will never leave and it can't ever be DELETED without some serious hacks to the Outlook program. That's not a client/server issue.



Anyone else have the same problem or find a simple solution?

zzzimba said:

When sending a large e-mail file in Win 7 Outlook, typically a large mp3 file, Outlook will sometimes get hung up and the e-mail will not leave the outbox. It stays stuck there trying to send repeatedly but never successfully, messing up everything else in Outlook. I have done lots of on-line homework and there are many more suggested simple solutions, but this is the only one that seems to get the job done: Delete a Message Stuck in the Outbox


It's a real pain! It took me about four hours to find the solution that works and then at least 30 minutes every time I have to research the article and then hack Outlook to free up the stuck email in the outbox. The MS corporate on-line forum teckies insist that it is a e-mail client server problem, which is absolutely false as many others also agree. I don't care if the e-mail does not get through as much as I just want to be able to delete it from the outbox when it gets hung up in a never ending loop of trying to send perpetually, eating up processing power, and it will never leave and it can't ever be DELETED without some serious hacks to the Outlook program. That's not a client/server issue.



Anyone else have the same problem or find a simple solution?

I'm sorry to contradict, but I think this is a server problem. If you send an attachment that is larger than the server-set limit, you'll run into problems. A common limit is 5Mb - are the troublesome files bigger than that? If so, how about breaking them up into sub-5Mb chunks using WinRAR (or similar), then have the recipient decompress and reassemble them, again using WinRAR, at the other end? That should avoid the problems with things getting stuck in the annoying loop. WinRAR has a 40 day trial period so you can find out if it is any use for you for free.

If you cant send via email; upload to another site, then send link e.g.
Mediafire.com (files)-(incldn mp3s)
imageshack.us (images)

Each ISP seems to have different file size limits. Find out from your ISP what they have. And then there is always the upload route as pixelpro suggests. Skydrive is another possibility.

i know some providers sizes:
Virgin= 20mb+
Sky=20mb+
talk talk= 10mb (around this)
.... trying to find more

Thanks for the suggestions so far gang but If you have not experienced this Outlook phenomenon personally (yet), it's really quite a tangled mess, and I never experienced it before myself until Win / Outlook 7 came along. While there have been some logical solutions and work-rounds suggested, they are aimed at treating some symptoms and do nothing for the main dis-ease.

For example, my last OS was XP. Whenever I exceeded my server's limits when sending an e-mail with attachments, I would get an "error message" back from the server saying that the file was too large and it could not sent. Well then, no big deal. I would just delete the email from the Outbox and go on to "plan B", whatever that may be. The problem now is that without executing the afore mentioned/linked hack in my first post, that over-sized email (in Win 7) will remain hung up in the outbox and enter into a never ending loop of trying to send it for 10 minutes and then just immediately begin again. There is no deleting it and no other human intervention is possible to terminate the process. Meanwhile Outlook is erratic and mostly useless. Shutting down Outlook and rebooting it only starts the cycle over again.

So, even if I am guilty of sending a file to large for my server (FYI - Its Yahoo Upgraded Premium subscription), why would my ISP be responsiblefor Outlook's bad behaviors and refusal to allow me to delete a message from the outbox? I've tried everything imaginable on several different occasions when this issue arises and I am convinced there is some kind of bug in Outlook 7's backside. If Outlook 7 refuses to allow deletion of an e-mail stuck in the outbox (and just tries to send it over and over and over)... is that an ISP issue?

I've done a fair amount of on-line homework to try and understand/correct the issue. It definitely seems to be a recognized popular problem in some help forums, and its not just my own imagination. But there seems to be no uniform consensus on its singular solution, or any MS confession that its another major hick-up in the Win 7 platform.

Am I crazy or can any one confirm who is still running XP that this problem is unique to Win 7? For example, try sending a oversized file relative to your server and if things don't work out, you will likely get an error message and then you can just delete that e-mail from the outbox. Am I right or am I crazy?

Thanks again for any thoughts on this matter!

Your friend, Zimba in San Antonio, TX

What you say sounds logical. Unfortunately I have to give up because I never used Outlook. I use AOL and never had any mail problems. AOL behaves exactly like you state regarding XP.

zzzimba said:

So, even if I am guilty of sending a file to large for my server (FYI - Its Yahoo Upgraded Premium subscription), why would my ISP be responsiblefor Outlook's bad behaviors and refusal to allow me to delete a message from the outbox? I've tried everything imaginable on several different occasions when this issue arises and I am convinced there is some kind of bug in Outlook 7's backside. If Outlook 7 refuses to allow deletion of an e-mail stuck in the outbox (and just tries to send it over and over and over)... is that an ISP issue?

It looks like Yahoo's limit for email attachments is 25Mb. Are the files that won't send bigger than that? When you attach a file to an email in Outlook, it will tell you the size, as in the screenshot below (a 34Mb MP3 by my favourite band :)). If it's bigger than 25Mb then don't send it. I think the problem is that for bigger files, Outlook tries to send, then the SMTP server eventually realises the attachment is too big and tries to bounce it back to you: without a blazingly fast connection, it's going to take a while to sort itself out.

One workaround would be to tell Outlook only to send emails when you want it to (you can change send/receive behaviour under Tools > Send/Receive > Send/Receive Settings...). That way, if you get a stuck email, you can force quit out of Outlook then restart it without it immediately trying to send again. That should allow you to delete the email without having to hack anything :)

Do you have your antivirus set to do email scanning? Try disabling the email integration or uninstall and reinstall without the email scanning feature.