I was able to get the issue solved through communication with DELL-Cares. It turned out that within Task Manager, Waves MaxxAudio Service Application somehow became disabled. After I enabled it and restarted the computer, the computer was able to recognize when a device was plugged in or disconnected again regardless of the status at the initial startup. 
I am currently having this issue with my XPS 8940. My earbuds do not seem to work in the 3.5mm audio jack on the front of the computer. Anytime I reboot my PC, the front headphone jack will work. But only if they are already plugged in. As soon as I unplug them or go to plug my earbuds in if they weren't there initially, the jack won't work unless I restart the computer again. I've tried updating the Realtek Audio drivers, using an older version of the driver and I can't seem to find a solution to this issue.  I have seen other threads on here with similar issues, and have yet to find a semi-permanent working solution outside of completely restarting my computer anytime I want to plug in earbuds. (Yes. I've tried multiple sets of earbuds and headphones.) The issue is that the jack doesn't recognize that anything is plugged in unless it is plugged in from startup. Any solutions?
XPS 8940, front audio jack doesn't recognize earbuds