Outlook 2011 error code 18500 - HTTP error. The server cannot fulfill the request

Question

When emailing large files we have started getting an error message "HTTP error. The server cannot fulfill the request".  This is when we are sending email attachments.  Any assistance would be greatly provided on how to resolve this issue.  

I did open Entourage 2008 and tried to email the file and it works successfully so I'm thinking there is some type of bug in Outlook 2011.

thanks

Answer 1

What version of Entourage? v12 or v13?

Entourage v13 and Outlook use EWS where Entourage v12 used WebDAV.

Make sure the Exchange Web Services (EWS) protocol enabled on the server. The OWA server needs the Exchange Web Services (EWS) protocol enabled

for Outlook to connect. See this for more information:

"Exchange Server Remote Connectivity Analyzer"

http://www.officeformachelp.com/outlook/exchange/exchange-server-remote-connectivity-analyzer/

Answer 2

I too couldn't send ANY emails at all from Outlook 2011 using my company's email (exchange) account.

Part Solution:

I've found if I turn off the "Use SSL to connect (recommended)" (found under "Advanced" in the Account settings), I can send some emails, but the folders don't synchronize readily, and I'm still not convinced this is the best solution.

Any emails with larger attachments (>500kb) still don't send (the status bar shows the email uploading completely, but then it hangs for 20 secs before spitting out the -18500 error message again).

History:

I too was experiencing problems sending emails with large attachments through my work email account, then the problem became sporadic, and now I can't send any emails at all. Not even an email with the word "Test" as the subject and in the body.

I have other exchange email accounts that work fine in Outlook 2011.

I can successfully send emails through Outlook 2010 (on a Windows machine), through the OWA client, and even from my iPhone!

Also, I can receive emails fine.

I used the connectivity analyzer (which seems to be designed more for Windows based machines), and the only error it came up with was:

"Testing TCP port 443 on host company.com to ensure it's listening and open.

The specified port is either blocked, not listening, or not producing the expected response.

A network error occurred while communicating with the remote host."

Following the "Tell me more about this issue and how to resolve it" link was useless, as it has solutions only for Windows operating system.

I have asked my company's I.T. dept for some assistance (e.g. an alternative port to connect to) - I will update should I get a response (our IT dept doesn't normally help anyone using anything other than Windows, so I'm not holding my breath)

If anyone knows of a work-around, or another standard port to use with SSL, PLEASE LET US KNOW!!!

Stich

Answer 3

If I can jump in on this thread (plz don't yell at me!), I'm experiencing this same issue with NO attachments and with *tiny* (like 2 words) emails.  I've already changed to Basic Authentication in EWS - IIS.

Anyone have any other ideas?

J

Answer 4

We are using an Exchange Server for Outlook 2011.  Email is 3MB and company max attachment size is 5MB. 

When sending emails without attachments the emails are sent just fine.

Answer 5

Are you using an exchange server configuration in Outlook 2011?

How big are the email attachments you are trying to send?

Also mention what happens when you send emails without attachments?

Entourage 2008 connects to the Exchange using WebDAV Outlook use WebServices. So it may work in Entourage but not in Outlook.