It looks like in that picture you are draining into a cooler/mash tun. Siphons work by differences in hydrostatic pressures (as explained above), so as you drain the keggle the water level in it drops, and as you fill your cooler, the water level rides. Even though your hose may technically be lower than the end of your pick up tube, if it is submerged in water in your cooler it is still working against the pressure of the water in the cooler, and can only drain to that level. In other words, the levels in your cooler and your keggle are reaching an equilibrium, and since there is no hydrostatic difference between the two at that point, the siphon ends. Recommendation: Lift your keggle a few inches, or lower your cooler a bit to re-establish a gradient between the two.
If that does not work, that you probably have some kind of air leak in your setup which is breaking siphon, but I don't think that is the case here.