Setup Rules to Ask Every Time

What exactly are the setup rules to make safe applicatons like Outlook, Spybot, and Ad-Aware, ask every time before being allowed to connect?

now this is new ;D
why do you want to do that?
i don’t have CIS on my comp right now. but i think you can edit the rule on:
CIS/FIrewall/advanced==> application rules

I would just like to know when certain applications try to connect out. When I change the default application rules for these safe applications to “ask”, then they don’t connect at all.

If you want to be alerted every time, remove all the entries for those applications in the firewall policy (Firewall > Advanced > Network Security Policy). Then whenever they want to connect, select “Allow” (but don’t check the “Remember my answer” box).

I’ve done that, but the next time I access the application, I’m not given a choice to allow them again because they are on some kind of safe list of applications and Comodo allows them to automatically connect.

You need to set the Firewall to “Custom” policy and put the “Alert settings” to at least high.

When set like this you will receive a pop-up for each application trying to access the net which doesnt have a policy for it in "Application Rules". You can then just answer the pop-up and the application will be allowed to connect out.Make sure you dont have “Remember my Answer” ticked or a rule will be created.