“Operating inside an opponent’s OODA loop” is Boyd’s primary device for dealing with opponents (he has other recommendations, primarily at the grand strategic level, for relationships with our own side and the uncommitted). He suggests its power in several places. Here’s probably the best known, from Patterns of Conflict:
And then later, in Strategic Game, where he places the concept into the “strategic game” of interaction and isolation:
Interesting theory, but what happens in real life? Pretty much the same thing. Here’s an observation by a former senior member of the Afghan government on the April 21, 2017, attack by the Taliban on an army base in the northern part of the country:
“The enemy has the strength — they have more people in their units now — and the speed of action,” said Rahmatullah Nabil, the former head of the Afghan intelligence service. “Unfortunately, we have slowed down our decision-making.” From the New York Times, “‘A Shortage of Coffins’ After Taliban Slaughter Unarmed Soldiers.“
Note that this comment could operate at not only the tactical level — how a force of 10 Taliban successfully attacked a major base — but also how the strategic situation in the country appears to be continuing to deteriorate.
Boyd never explicitly defined “operating inside the OODA loop.” Perhaps the closest he came was at the top of the left column on Chart 132. I don’t know whether he considered the concept to be self-evident, or whether he was using the classic Zen technique of pointing, rather than explaining.
Slightly East of New 
But our staffs are bigger than theirs! I refer, of course, not to the staff as a physical weapon (a rod made of wood or metal) but to the staff as a powerful weapon of combat, the intellectual juggernauts driving the US military.
These are large groups of men and women — finely educated (many with advanced degrees) — backed by vast arrays of machines providing data, analysis, and communication. With all this our OODA loops must crush those of the Taliban and ISIS.
Combined with our almost unbelievable superiority in weapons and transportation equipment, this gives us a kind of superiority seldom seen in war. It’s like those scenes in westerns when the indians charge — to be blown away by a gattling gun.
Plus, in some (many?) engagements our foes don’t even have greater numbers. (The example you cite of 10 Taliban successfully attacking a base is a raid, a special case of this.)
What would Boyd say about our situation in year 16 of our intervention in Afghanistan? Perhaps a big picture Boyd-like analysis might help more than looking at the details, or at least provide a starting point for more granular analysis.
Probably why Boyd didn’t make general.
Exactly. He was more interested in winning.
When it comes down to being inconspicuous, and if you are already in your opponent’s OODA loop, then the advantage of inconspicuous behavior comes down to what your position and posture is.
If you (as an image of position and posture) are the one with the advantage in the environment, the OODA loop is operating in, then inconspicuous isn’t as important as being the one making the quicker decisions and making faster transients, from the advantage your position and posture gives you.
I mean, an inconspicuous act can slow decision making down and make you look weak, and no negotiations can take place from a position with no advantage or a posture that appears weak. The US is trying to prop up a military force who needs to negotiate between the civil and military elements inside Afghanistan.
As it happens, there probably are still solders in the Afghan army who could still say that “we were all Taliban at one time” or another. The Brits didn’t negotiate with a weak force in our Revolutionary war, and there is no reason the US should negotiate with a weak force in Afghanistan.
If the Afghan military has no advantage in the environment they are fighting in, there will be no negotiations, because they can’t survive with no advantage recognisable.
In fact, I believe negotiations between the US and the Taliban is pretty much useless, unless the negotiations is in an effort to rid their country of ISIS, the US wants to occupy Afghanistan forever, or the US wants the Taliban to give them lip service (so, like Russia, the US can go home) as the Taliban make use of their position and posture inside the OODA loop to fold up the Afghan government and government forces.
General McCrystal had a strategy that he applied to Afghanistan that historically was a winning strategy. It was judged good/bad instead of winning/losing and bad won. I have not heard of any other strategy except to give the Afghan people a future worth living and prop up the Afghan forces until they can give them that future (which I am not so sure it is even a future the Afghan forces really want).
Such a strategy doesn’t make much use of an OODA loop, but McChrystal’s strategy seemed to. An OODA loop makes use of both the distributive and decentralized network structure by drawing the line between war and peace between Observation and Orientation.
Orientation is a form of isolation involving all the advantages within the same environment. Isolation means to kill your enemy, but, in Observation, that is not all it means. It means harmonizing (or reharmonizing) what is seen, in Observation, with the actions of the decisions coming out of one’s Orientation with another.
I guess we just should be glad that the Trump administration is helping in the Taliban’s effort in ridding the country of ISIS and at the same time able to maintain forces that are still able to support the Afghan military.