You could try an app like Calendar Event Pro which lets you set custom alert times.

Try looking at the trouble-shooting guide provided by Apple: http://support.apple.com/kb/TS4000 Cheers, Geoff aka tyreless

In Outlook there should be a new separate iCloud calendar. Is it there? If it is then you need to make your changes on that calendar. By default Outlook will open its "default" calendar rather than the iCloud calendar so you need to select the iCloud calendar. It's a bit kludgey. Geoff aka tyreless

Thanks Marcitz. I now see that it does work (with the caveats you mention). It is kludgey but it is better then my previous solutions which would only update between devices every 15-30 minutes. Via iCloud it happens within a minute usually. I found a trouble-shooting web page that might help...

Spoke too soon. New Tasks and New Reminders are not being synced to Outlook.

There is a better way. You need to install iCloud for Windows (available from the Apple web site). Install it, run the setup (it takes time) and your Reminders are synced with Outlook. You can also sync your calendar and contacts this way. You need Windows 7 or Vista and Outlook 2007 or 2010...