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Outlook 2011 saving messages as drafts

Posted on 2013-12-02
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Last Modified: 2013-12-17
1 Exchange 2010 SP2 RU6 (all roles) on 2008 R2
Mixed environment Windows 7 SP1/Office 2010
Mac OS 10.7/10.8 Office 2011 SP2/SP3

Since last Wednesday November 27 the Mac users are randomly experiencing the following error

"HTTP error. the server cannot fulfill the request.
mail could not be sent. the message has been moved to your drafs folder
error code: -18500"

It is not each Mac user and it doesn't seem to be related to messages with attachments or no attachments, replies or newly composed messages. The only change in the infrastructure is I renewed the Exchange Certificate the prior Friday November 22. No other patches have been applied to the server. I have read articles about modifying the web.config file value "httpRuntime maxRequestLength="30000" however my current value is 2097151 so I have not reduced it to the recommended setting.
There are many forums which discuss this but no one seems to have come up with a solution.
Thanks in advance.
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Question by:PM_IT
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Simon Butler (Sembee) earned 500 total points
ID: 39692060
Any reason you aren't on Exchange 2010 SP3? I would suggest upgrading to the latest service pack to begin with.

Simon.
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by:PM_IT
ID: 39692415
I have not gone through my patching cycle and therefore have not upgraded to SP3 for Exchange. I agree it should be installed but that doesn't account for the sudden change in Mac Outlook 2011 behavior.
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Expert Comment

by:Simon Butler (Sembee)
ID: 39692642
Exchange 2010 SP3 has been available almost ten months - it doesn't come down in Automatic Updates. Therefore unless you operate an annual patching cycle you have had plenty of opportunities to keep the server up to date.

When you renewed the certificate was that a trusted or self signed certificate?

However until the server is up to date, that is about the most I can assist you with. If you were to call Microsoft support with the problem they would say the same thing - install the updates that you are missing.

Simon.
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by:PM_IT
ID: 39692710
Certificate is trusted from GoDaddy and I appreciate the patching advice. Still doesn't explain that all of a sudden this issue is cropping up randomly on the Mac machines.
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Author Comment

by:PM_IT
ID: 39723867
Installed SP3 and issue has been cleared
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