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Outlook on Mac will not send large attachments despite Exchange connector settings

The problem stems from Outlook on Mac using Outlook Anywhere. The solution is to increase the EWS limits manually

  1. Open IIS from admin tools
  2. Navigate into
    1. SBS 2008: Sites / SBS Web Applications / EWS
    2. SBS 2011 or other: Sites / Default Web Site / EWS
  3. Right click on EWS and click Explore
  4. Make a copy of the file web.config and open the existing one in notepad.
  5. Find the line <httpRuntime maxRequestLength=”13280″ />, which stands for about 13mb, and change it to <httpRuntime maxRequestLength=”20000″ /> for 20mb or 50000 for 50mb, etc.
  6. Save the file and try again. I did not have to run resetiis or anything like that to get it working. Remember a large email can take 5-10 minutes to send.