01 CAt Man Do

Well...in your case it certainly wouldn't help since you have the lamp flipped upside down. Personally I never put any kind of faith in some of those rubber flaps. FWIW I've been caught in rain more than a couple times now and with the remote wire plugged in I've yet to have a problem. I suppose if you wanted to you could use an eye dropper and put in a little alcohol to dry the port out when you get home. There is also the option of using some electrical tape to put around the port and wire if you use an extension. Of course I forgot that in the event of running into rain you also have the option of just pulling out the extension and closing off the port with the rubber flap. In your case the idea of using an extension is just to prevent over-wear of the port. Perfectly fine to take the wire out once in a while. The port on my lamp gets twice the wear and tear because it also is used with a remote control wire. Still, I got a good two years out of it. Too bad I didn't figure out how to save wear and tear on the port until it broke.

Odd that you mentioned wanting to use the rubber flap to protect the port. I have numerous small front and rear LED self-contained lamps where the flap just stopped working or simply broke off. These lamps keep working which amazes me because I'm sure they've seen their share of getting wet.

Only time I ever had an issue with a port not working after getting wet was with my phone. Odd too because I have the phone inside a plastic holder and mounted on my stem. Somehow some water got into the port and when I tried to charge the phone after taking it out, the phone gave me a prompt telling me I couldn't charge the phone till the port dried out. Since I had no alcohol to help it dry out it took about an hour before I could charge the phone.