iPhone sending attachment problems Sending this message failed

When you use certificate authentication you have to set the uploadReadAheadSize in the IIS metabase to your max email size, the default is 48KB so nearly any attachment cannot be sent/forwarded.

With the following command you can change the value (in this case 10MB):

C:\Windows\System32\inetsrv\appcmd.exe set config -section:system.webServer/serverRuntime /uploadReadAheadSize:"10485760" /commit:apphost

C:\Windows\System32\inetsrv\appcmd.exe set config “Default Web Site” -section:system.webServer/serverRuntime /uploadReadAheadSize:”10485760″ /commit:apphost

After this restart the IISAdmin service to affect the change.

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