Good news: US Special Ops raids ISIS in Syria, frees an enslaved woman.
Bad news: Iraq lost Ramadi to ISIS.
So, are we winning or losing? There are a few ways to answer this, but my overwhelming urge is to ask for patience and skepticism of all claims. Why? Because wars are complicated things, especially wars of this kind, where the daily news tends not to be a good barometer of progress. Were the Nazis winning on Dec 20th, 1944? Well, no. The Battle of the Bulge was a setback, but by that time, Germany's future was already determined. The only question was really where the line would be drawn between the Soviet occupation and Western occupation. I can only imagine the abuse Ike would have gotten on twitter on June 15th: sure, you landed the troops on Normandy, but they are stuck, so #epicfail #Ikeisanidiot etc.
So, the US and its allies seem to be getting better intel if they can find the guy they sought with no serious casualties.
But the Iraq training/mentoring effort clearly has not had enough time or size to make that much of a difference, I think.
Of course, the key to all of this is not how many guns are in the hands of "our friends" but the politics of the place. And that, alas, is not going well, at least as far as we can tell from here. The Shia dominated government has not made a deal with the Sunnis ... worse, the government has become more dependent on the Shia militias and Iran. This makes it harder for any Sunnis fed up with ISIS to switch sides. No credible commitments made by the Iraq government means no flipping by the Sunnis, which means that the bad guys have easy recruitment and we may not get as much actionable intel.
In war, it is always about politics but much more so in counter-insurgency. So, yeah, skepticism is the order of the day.