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Trouble sending large attachements from Outlook on MAC

This is an old one I found in some stored personal information, so putting it up here in case someone find the need for this.

Issue is regarding sending attachements from an Outlook client on Mac.
This specific one was on Outlook 2011 for Mac.
Exchange server via Small Business Server 2008.

When sending email attachements with size larger than 10Mb, sending fails, and messages goes to the drafts folder in Outlook..

Pulling som email flow settings from the server showed the following.

No limitations in send size.

Some webcrawling showed that this is a known problem with Microsoft Exchange against Entourage and Outlook for Mac.
The solution is to make som changes to IIS and the web.config file located at %windir%\system32\inetsrv folder on the exchange server.

The following guide is adjusted to this case, on a SBS 2008 server:

  1. Change “maxAllowedContentLength” parameter in “web.config” file:

    From CMD change folder to “%windir%\system32\inetsrv\” and run below command:
    appcmd set config “SBS Web Applications/owa” -section:requestFiltering -requestLimits.maxAllowedContentLength:<XX>

    XX” is the desired value in Bytes

    (The above command creates the value if it not already exists. To check if it exists, run the following from a comand promt (as admin).:

    %WINDIR%\System32\inetsrv\appcmd list config “SBS Web Applications/owa” > currentConfig.txt & notepad currentConfig.txt»

    This opens current config in notepad, and you can search for the maxAllowedContentLengt setting here. If it dont exists, add it by running the command in step 1

  2. Change “maxRequestLength” parameter in “web.config” file:

    Open “web.config” file located in the EWS Virtual directory “Microsoft\Exchange Server\ClientAccess\exchweb\EWS will have the following entry
    <httpRuntime maxRequestLength=”13280″ />

    By default, the max request size is approximately 13MB.

    Change the item <httpRuntime maxRequestLength=”13280″ /> to <httpRuntime maxRequestLength=”XX” />

    Where “XX” is the desired value in Kilo Bytes.

  3. Change “executionTimeout”  parameter in “web.config” file:

    Open web.config file located in the EWS Virtual directory “Microsoft\Exchange Server\ClientAccess\exchweb\EWS

    Change the item <httpRuntime maxRequestLength=”13280″ /> to <httpRuntime executionTimeout=”X” maxRequestLength=”13280″ />

    Where “X” is the desired time in seconds. Example value 600 for 10 minutes. Make sure the value is greater than the time it takes to upload the file.

  4. Change “connectionTimeout settings in IIS.

    Open “IIS Manager” > select “Default Web Site” > Click “Advanced Settings” > select “Connection Timeout” and change the value in Seconds (make sure the value is greater than the time it take to upload the file)

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