I cheat and have a shortcut to my dialup connection on my desktop, and click that to start the dialup process, before opening Outlook or Internet Explorer.
If you go to Double-click the My Computer icon on your desktop to open it and then double0click the Dial-Up Networking folder, you will see your Dial-up connection(s). Right-click the one you use most often and select Create Shortcut. You should get a pop-up window saying that Windows cannot create a shortcut here. Do you want the shortcut to be placed on the desktop instead?
Just click Yes.
Now, whenever you want to start your dial-up to access mails or internet, double-click the shortcut first, and a dial-up box that looks different from the one you are used to will appear. Just click the Connect button to start it dialing.