The factory drip rail has small weep holes at each corner, but they are sometimes filled with layers of paint of seam seal. Check to make sure they are openend up and draining properly.
In lieu of running windshield sealant, if your windshield grommet is dry-rotted, cracked or not sealed properly, I suggest having a new one installed. I found a local automotive glass shop in my area, that works on the old stuff. They will remove the old, dispose of it, provide a new windshield and install it for under $200.00, with a warranty. Perhaps a glass shop would do the grommet replacement for less. If you intend to keep your truck, replacing the grommet is a wise investment, to eliminate the water seepage issues in the future.
