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SeptAdmin

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Outlook 2011 for MAC with Exchange 2010 HTTP Error -18500 when sending email

We recently installed Outlook 2011 for MAC after we moved a users mailbox to our new Exchange 2010 SP1 server.  Outlook is able to connect to exchange and download all emails, calendar, etc... however when you send an email you receive the following message:

HTTP error. The server cannot fulfill the request.

Mail could not be sent.  The message has been moved to your Drafts folder.

Account name: "Exchange"
Error code: -18500

I can see that the email has been moved to the drafts folder.  OWA works on the MAC, Outlook 2010 on PC also work with no issues.  I can even see the email moved into the drafts folder in OWA.

I have searched everywhere and most people seem to have this issue with large attachments but it happens for every email that I send.  I have done the fixes for the large attachments hoping that would fix it but no luck so far.

Any assistance anyone could give would be greatly appreciated!
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Xaelian
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Have you enabled the Exchange Web Services (EWS) protocol? This is needed.

Use this link to analyze it. If it's not enabled or there is a mistake with it, it will show you.
http://www.officeformachelp.com/outlook/exchange/exchange-server-remote-connectivity-analyzer/
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SeptAdmin

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Yes EWS is enabled.  I ran the test from the link you sent and everything worked fine.  It did not report any errors for EWS connectivity.  For the test you have to use an account with an empty inbox, so i created a new user to do the testing with.  

To make sure that it wasn't a user problem I created a new account in Outlook 2011 for my test user.  It also received the same error when trying to send an email.
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Xaelian
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Thanks Xaelian! I was able to determine that the problem was a misconfiguration with Autodiscover.  Once i corrected it emails started sending.
Avatar of Kotteeswaran Rajendran
This is a issue with product which the "BUG" team is aware of. The product team is closely working towards resolution. The resolution will come with next build. Till then enjoy using OWA for over-sized attachment. No matter wherever you search , post or go unfortunately this is it :(
FYI :  http://community.office365.com/en-us/forums/153/t/209414.aspx ---  "All users who are on Version 15.0 Build (837.10) on the O365 Server will experience this issue".  No luck till next build