We help IT Professionals succeed at work.

Entourage Client on Snow Leopard connecting to Exchange.

OxygenITSolutions
on
1,010 Views
Last Modified: 2013-11-08
Sending an attachment and getting this error on Entourage/Exchange.

Could not Synchronize Record to Exchange server Error -18500

and

HTTP error. The server cannot fulfill the request.

Mail could not be sent. The message has been moved to your Drafts folder. Account Name: XXXXX

Error -18500

Please help.
Comment
Watch Question

CERTIFIED EXPERT

Commented:
Does this happen with all attachments? If not, perhaps the attachment in question exceeds the maximum size permitted by your server.

Also see:  http://www.entourage.mvps.org/

By the way, if you are using OS 10.6, why not switch from Entourage to the Mac's built in mail client? See:

http://www.apple.com/macosx/exchange/

and

http://images.apple.com/macosx/exchange/docs/MacOSXSL_Exchange.pdf
Cris HannaSr IT Support Engineer
CERTIFIED EXPERT

Commented:
You've placed this in the Small Business Server zone so I'm assuming you're using SBS...if so, which version
CERTIFIED EXPERT

Commented:
By the way, there is no need to use Entourage on the Mac if the Mac is using OS 10.6. The built in Mail, iCal and Address Book programs have Exchange support:

http://www.apple.com/macosx/exchange/

and  

http://images.apple.com/macosx/exchange/docs/MacOSXSL_Exchange.pdf


To find out if the Mac is running OS 10.6, pull down the Apple Menu to "About this Mac".
CERTIFIED EXPERT

Commented:
Ignore last post which was intended for a different thread.

Author

Commented:
Using 2008. Customer wants Entourage.
Cris HannaSr IT Support Engineer
CERTIFIED EXPERT

Commented:
So just to be clear.  You have SBS 2008, with a Mac running Entourage and there is a problem sending mail with attachments?   Can you send mail without attachments?   Can you receive mail in Entourage without issue?

Author

Commented:
Mail is fine. Just this one particular message sending an attachment. Send and receive normal files and attachments seem fine. Attachment isn't too large. Just gives this one error. SBS 2008.
Cris HannaSr IT Support Engineer
CERTIFIED EXPERT

Commented:
what kind of attachment
CERTIFIED EXPERT

Commented:
Might the SBS security be set to reject certain types of files,.exe files for instance? Or is it possible that that file name contains a character that is legal on a Mac, but illegal on Windows?  See:

http://www.macwindows.com/tutfiles.html#DifferencesFiles

Author

Commented:
SBS Service Pack for Exchange (SP1 or similar) fixed the issue. In fact, it fixed a number of issues relating to Exchange errors.
Sr IT Support Engineer
CERTIFIED EXPERT
Commented:
This one is on us!
(Get your first solution completely free - no credit card required)
UNLOCK SOLUTION

Commented:
This is not the solution to this problem... We still have the same problem with all macs running either Mac Mail or Entourage (WSE) and a brand new 2010 Exchange server that is completely up to date.   It seems there is a size limit for attachments hidden somewhere. we've tried a couple things but cannot find the true cause or solution!

Gain unlimited access to on-demand training courses with an Experts Exchange subscription.

Get Access
Why Experts Exchange?

Experts Exchange always has the answer, or at the least points me in the correct direction! It is like having another employee that is extremely experienced.

Jim Murphy
Programmer at Smart IT Solutions

When asked, what has been your best career decision?

Deciding to stick with EE.

Mohamed Asif
Technical Department Head

Being involved with EE helped me to grow personally and professionally.

Carl Webster
CTP, Sr Infrastructure Consultant
Empower Your Career
Did You Know?

We've partnered with two important charities to provide clean water and computer science education to those who need it most. READ MORE

Ask ANY Question

Connect with Certified Experts to gain insight and support on specific technology challenges including:

  • Troubleshooting
  • Research
  • Professional Opinions
Unlock the solution to this question.
Join our community and discover your potential

Experts Exchange is the only place where you can interact directly with leading experts in the technology field. Become a member today and access the collective knowledge of thousands of technology experts.

*This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

OR

Please enter a first name

Please enter a last name

8+ characters (letters, numbers, and a symbol)

By clicking, you agree to the Terms of Use and Privacy Policy.