I've heard this word used before but I can't remember it!
I've heard it used to describe wars like Iraq and Vietnam. Something you can't escape easily and is causing large problems, like a pit? Here is an example:
The American government has decided to pour extra money into the war in Iraq, unable to escape the ______ it has entered.
"Quagmire" is certainly a fitting word for your example:
"The American government has decided to pour extra money into the war in Iraq, unable to escape the quagmire it has entered."
Definition from M-WO:
2: a situation that is hard to deal with or get out of : a situation that is full of problems
The first definition (also from M-WO) is helpful in understanding how "quagmire" came to be used for other tricky, dangerous situations:
1: soft miry land that shakes or yields under the foot
EDIT: "Quagmire" was apparently quite commonly used to describe the US' involvement in the Vietnam War as is illustrated in the book, "The Making of a Quagmire: America and Vietnam During the Kennedy Era" by David Halberstam, Daniel J. Singal (Editor & Contributor)
The answer to the title is kafkaesque.
of, relating to, or suggestive of Franz Kafka or his writings; especially : having a nightmarishly complex, bizarre, or illogical quality <Kafkaesque bureaucratic delays>
But the answer in your example is quagmire.
In Greek mythology Sisyphus was punished with the task of rolling a boulder uphill for eternity. Each day the boulder would roll back down and he would have to roll it up again. This endless, pointless toil lends us
Sisyphean Endless or unavailing (Dictionary.com)
and thus giving you a sisyphean task
"It's a trap!" — Admiral Ackbar, Star Wars
Trap — M-W
something by which one is caught or stopped unawares; also: a position or situation from which it is difficult or impossible to escape
Then there's the vulgar slang,
Clusterfuck — ODO A disastrously mishandled situation or undertaking.
A chaotic situation where everything seems to go wrong. It is often caused by incompetence, communication failure, or a complex environment.
Quoted example:
The American government has decided to pour extra money into the war in Iraq, unable to escape the clusterfuck it has entered.
If you're thinking of a phrase including the word pit, you're probably thinking of tar pit:
A tar pit, or more accurately an asphalt pit or asphalt lake, is the result of a type of petroleum seep where subterranean bitumen leaks to the surface, creating a large area of natural asphalt.
...
Animals usually cannot escape from the asphalt when they fall in, making these pits excellent places to excavate bones of prehistoric animals. The tar pits can trap animals because the asphalt that seeps up from underground forms a bitumen pit so thick that even mammoths could not free themselves before they died of starvation, exhaustion from trying to escape, or exposure to the sun's heat.
US a bottomless pit. (Typically with throw and down as in the examples.) Why do they keep throwing money down that rathole?
McGraw-Hill's Dictionary of American Slang and Colloquial Expressionsp
"If you want to see a change, the only way that's going to happen is if we elect Joe and others like Joe to join with the increasingly large number of Republicans who have seen the light," he continued. "If we elect Joe's opponent and his colleagues, nothing is going to change in Iraq, except we're going to continue to go down this rathole."
The American government has decided to pour extra money into the war in Iraq, unable to escape the rathole it has gone down.
also goatfuck (US military slang, vulgar)
A confusing, disorganized situation often attributed to or marked by human error.
A highly contentious or hazardous situation.
A troublesome situation or place in which there are many dangers.
What I was talking about was this administration’s decision to make Iraq part of its war on terrorism, but what I was thinking about was Vietnam. It was not because of nostalgia or political partisanship (after all, it was liberal Democrats who got us into the war in Southeast Asia and neocon Republicans who sent us into the hornet’s nest of Iraq) that I thought about and mentioned Vietnam, but because it was the same kind of dangerous spin that had given us Vietnam and dragged us into Iraq...
While the president struggled to keep his promise of withdrawing from the hornet's nest of Vietnam, Congress showed its newfound power by adopting a series of amendments restricting the ability of the U.S. to go to war...
The American government has decided to pour extra money into the war in Iraq, unable to escape the hornet's nest it has entered.
You could consider:
impasse http://www.dictionary.com/browse/impasse
a position or situation from which there is no escape; deadlock.
stalemate - http://www.dictionary.com/browse/stalemate
any position or situation in which no action can be taken or progress made; deadlock:
... or synonyms thereof.
I'd suggest
omnishambles
which was coined by the writers of the British political satire The Thick Of It in 2009, and then named word of the day by the Oxford English Dictionary in 2012.
It refers to a situation that has been characterised by a whole series of errors and blunders and is now beyond the point of rescue.
You might have been thinking of a pitfall.
OED:
A hidden or unsuspected danger or difficulty.
Emphasis mine.
Can of worms comes to mind.
A situation that, once started, is likely to become problematic or have a negative outcome.
Sentence,
Getting involved in the minor border conflict has become a can of worms for the country, with no end to the military engagement in sight. (source)
You might also like imbroglio or mare's nest.
I'm thinking of quandary:
A state of perplexity or uncertainty over what to do in a difficult situation:
Kate was in a quandary
A difficult situation; a practical dilemma: a legal quandary
From the Oxford dictionary.
Quagmire certainly captures the difficulty in escaping a situation and the problems associated with it, but does not seem to capture the futility and pointlessness of the situation itself.
How about something a bit more poetic from "Charge of the Light Brigade"
Just to try it on for size:
The American government has decided to pour extra money into the war in Iraq, unable to escape the valley of Death it has entered.
Well, if you don't mind using a 3-word pop-culture reference for this, you can use "Kobayashi Maru scenario".
From Wikipedia:
In the scenario of the 2280s, the cadet receives a distress signal stating that the civilian freighter Kobayashi Maru has struck a gravitic mine in the Klingon Neutral Zone and is rapidly losing power, hull integrity and life support. Sensor readings are indeterminate and there is no way to verify the distress signal. There are no other vessels nearby. The cadet must quickly take a decision:
Attempt to rescue the Kobayashi Maru's crew and passengers, which involves violating the Neutral Zone and potentially provoking the Klingons into hostile action or an all-out war; or
Abandon the Kobayashi Maru, potentially preventing war but leaving the crew and passengers to die.
...snip...
The objective of the test is not for the cadet to outfight or outplan the opponent but rather to force the cadet into a no-win situation and observe how he/she reacts.
And it would perfectly fit the OP's original statement:
The American government has decided to pour extra money into the war in Iraq, unable to escape the Kobayashi Maru scenario it has entered.
HTH.
(P.S. And, yes, we all know that Capt. Kirk was able to beat the Kobayashi Maru scenario, but he finally had to admit he cheated to do it.)
What about imminent or impending failure?
adjective: imminent 1. about to happen.
and
verb gerund or present participle: impending be about to happen.
An albatross is a favorite of mine. From Merriam-Webster:
a continuing problem that makes it difficult or impossible to do or achieve something
and from dictionary.com
something burdensome that impedes action or progress
