Cant send email with Outlook with attachment

I am getting a timed out message when trying to send an email with an attachment. If the attachment is a small file it goes through no problem. But if it is bigger like over 1MB then it does not send. Sometimes if I leave it in the outbox it will send later on after multiple attempts.

I have road runner cable Internet access. I am not sure what the max size of an attachment is but it is well over a few megs.

Any ideas?

THANKS

 

I forgot to add that I called road runner tech support and they are basically worthless. The wanted me to re-install outlook and so on. My internet connection is otherwise working perfectly. I had this problem in the past and reinstalling and all that did not fix it.

 

here is what just happened. I sent an email from my RR address to my yahoo address with a 2MB pic attached. I got the same operation timed out error.
I deleted the email from the outbox since it would not send then hit the send/recieve button and recieved the message on my yahoo account 3 times.

 

OS and Outlook versions?

 

XP Pro version 5.1.2600 SP 2 Build 2600
Outlook 2003 (11.6359.6408) SP1

 

Things to try - all are general clean-up and at best, your issue goes away. At worst will leave your system running a little better and we continue troubleshooting on a known clean system.

- Open My Computer. Right-click on the icon for your system drive and left-click Properties. Click the cleanup button and when it finishes the scan, check all items in the suggested list.

- Click on start, on run, key in sfc /scannow (note the space after sfc) and OK.

- Click on start, on run, key in cmd and when the cmd window opens, key in chkdsk /f and ENTER. Answer Yes to doing the deed at next boot and reboot.

 

I would say that 1MB is probably bigger than the limit per email for one of the ISPs.

If you go to the tools/ accounts/ select the account/ properties/ advanced
There should be a slider to extend server time outs and to break apart large emails.

See if you can find the exact limit. Like does 999KB go through and not 1MB?

 

I emailed Roadrunner and they replied with this:
"The maximum email size you can send with attachment is 5 megabytes. "


Newt,
I am doing what you suggested now. The disc clean up is slow.
Thanks

 

I believe Yahoo has a 1.5MB limit, but it may be smaller (I saw a reference to 1024KB )

 

With a free Yahoo! Mail account, you can send and receive messages up to 10MB.

Yahoo! Mail Plus users can send and receive up to 20 MB

================

this is a wierd problem.
I just sent a 2 mb pic from my Yahoo address and again from my RR address bot being sent to myself.

Outlook tried sending them and gave me error messages everytime it tried to send. I deleted them from Outlooks OUTBOX and them checked for new mail.

I recieved the messages from both yahoo and RR 3 times each.
It looks like Outlook is not removing them from the outbox once they are sent. and it is trying to send them over and over since they are still in the outbox.
what the hell?

 

Could be an issue at your ISP and if so, nothing you do locally will help.

See if they can offer any help. Might help to email a link to this thread so they have good background on the issue.

 

I have roadrunner isp and the e-mail help pages I read mentioned a 10MB mailbox limit and a max file size for attachment of 10MB. I frequently send and receive files much larger than 2MB with no problems.
One thing you might check is your virus protection program, mine scans all messages coming or going but is pretty fast. Although I notice that after I click "send" the mail sends and the scanner checks it before it goes, usually about 10 seconds or so, maybe your scanner is slower and your timeout settings are too small.
Just thinking out loud.

Mike

 

Mike,
I took your advice and looked around for the time out setting. I couldnt find it so I did a search of the Outlook Help for timed out. It came back with a description of exactly what is happening. I followed the steps. Now all I have ot do is test it out. I moved the server time out to 3 min. 30 sec.

THANKS! John

The steps for anyone who searches and needs help:

E-mail message with an attachment is sent repeatedly to recipients

Applies to Microsoft Office Outlook® 2003, Microsoft Outlook® 2002

When you send an e-mail message with a large attachment, you might experience situations where that message is sent repeatedly to recipients "” until you delete the message from your Outlook Outbox. The message never appears in your Sent Items folder.

The problem might be related to the connection time-out to your Internet service provider (ISP) (ISP: A business that provides access to the Internet for such things as electronic mail, chat rooms, or use of the World Wide Web. Some ISPs are multinational, offering access in many locations, while others are limited to a specific region.) e-mail server. If the size of the attachment in the e-mail message is too large, the e-mail message cannot be sent within the time limit. As a result, the message is sent repeatedly. To resolve this issue, use the following options:

Option 1: Increase the server time-out limit

1. On the Tools menu, click E-mail Accounts.
2. Click View or change existing e-mail accounts, and then click Next.
3. In the list, click the e-mail account that you want, and then click Change.
4. Click More Settings, and then click the Advanced tab.
5. To increase the maximum time duration for e-mail server connections, under Server Timeouts, drag the slider control.
6. Click OK.
7. Click Next, and then click Finish.

Option 2: Compress the file you are attaching to the message

Zipping a file creates a compressed version of the file that is considerably smaller than the original file. File types that are reduced the most after zipping are text-oriented file types, such as .txt, .doc, and .xls, and graphics files that use noncompressed file types such as .bmp.

See the See Also section in this article for information about zipping files.

 

**** .... i changed teh time out to 3min 30 sec and the message still stayed in the outbox but it sent like 6 or 7 times in the 3 and a half minutes. It is a 2 mb zip file.

I guess the problem is not solved.

 

hellmaster--In oshwyn5's post #7 he mentions that Outlook may also have the ability to break a message/attachment into smaller portions. Outlook Express does. Have you tried that?

 

No, I have not tried that. For Roadrunner:
"The maximum email size you can send with attachment is 5 megabytes. "

I dont think I have a need to break apart emails smaller than 5 MB.

 

Timeouts

Your email is timing out before it finishes sending the large file. In outlook, go to tools, email accounts, change, more settings, advanced and in server timeouts, increase the default setting of 1 minute to 9. This should solve your problem.

 

maybe I didnt explain it correctly.
outlook is sending the email multiple times then I am getting the timed out error message and the email stays in the outbox. later on it tries to send the email again. it sends it multiple times then gives the timed out error and leaves it in the outbox. this process goes on over and over and the recipient get the same emial many, many times until I see what is happening and delete it from the outbox.

i played around with the server time out setting and does not matter how long or short the time out is, it still does it.