Riddle Mastery

I have often been called a Riddle Master due to my love of inventing riddles and tormenting people with them; though, paradoxically, I am terrible at solving them myself. Which is why I prefer the title Riddle Maker. Fun fact: I have found that children grades 3-6 are the uncontested best at solving riddles; far better on average than teenagers and up leastways. Any guesses as to why? (I know the answer, so consider this a quasi-riddle.)

It is sad really that the art of making and answering riddles has been so diminished since the advent of modern history, or at least since collapse of the time-honored respectability granted to Bards, storytellers, and others who partake in oral traditions.

"The riddle-game was sacred and of immense antiquity, and even wicked creatures were afraid to cheat when they played at it." - J.R.R. Tolkien

These days it is only those who works within the realms of Fantasy who wholly and truly appreciate the power and potency of riddles, a far cry from when Kings and Heroes placed great weight upon them. Then again, why not? For in the Fantasy genre lives the misty mystery of the ancient past, and so we glory in the enigmatic and such puzzles as twists minds into first comprehending and then solving Gordian Knots. However, true and masterful usage of riddles is rare even within Fantasy literature. 

Riddles in Fantasy: 
On that note, those Fantasy authors who do employ concept of riddles will 99% employ Riddle Games as its main element. J.R.R. Tolkien hosts a famous one between Bilbo and Gollum in The Hobbit, the stake being Bilbo's life and freedom.
In The Grey King, the third book of Susan Cooper's fantasy sequence The Dark is Rising, Will and Bran must win a Riddle Game to gain a...special power necessary for the Light in their war against the Dark.
A sphinx appeared in the third task in Harry Potter and the Goblet of Fire, guarding the final trophy. To get past, one must answer a riddle about a spider.
In Stephen King's The Dark Tower III: The Waste Lands and The Dark Tower IV: Wizard and Glass, the ka-tet must riddle against Blaine the Mono in order to save their lives. (Of course, seeing as I have read neither of these books, this is only a secondhand account).

But, in my not entirely humble opinion, no Fantasy author makes better use of riddles than Patricia A. McKillip in her books The Forgotten Beasts of Eld and The Riddle-Master trilogy.
In the latter, the ancient art of riddlery is taught at the College of Caithnard - the study based on books recovered from the ruins of the School of Wizards. The riddles in the series are composed of three parts - the question, the answer, and the stricture - and are both a way of recording history and a guide to living life. Riddles play a crucial role in the series, the main protagonist, Morgon of Hed, beginning his journey by winning the crown of the kings of Aum in a Riddle Game with the ancient ghost of Peven of Aum; Peven had a standing wager going that no one could win a riddle-game with him, and those who lost against him forfeited their lives. (This is not a real spoiler, as the reader learns all this and more within the first chapter or two)
"Beware the unanswered riddle."

Here is an (easy) riddle I created:
What plays with words and logic, yet never tells a lie = ?


Actual History:
As aforesaid, once upon a time the art of Riddle Mastery was taken quite seriously, as evidenced by a certain Greek philosopher whose tomb was just (at the time of writing) uncovered speaking so fondly of a passion of mine.

Ancient Greek Sphinx from Delphi
"Good riddles do, in general, provide us with satisfactory metaphors; for metaphors imply riddles, and therefore a good riddle can furnish a good metaphor." - Aristotle

Indeed, riddles and Riddle Games are not mere tools, mere elements, of mythology and Fantasy literature alone. Professor Archer Taylor of Pennsylvania, a seminal proverb and riddle scholar and folklorist, says that "we can probably say that riddling is a universal art" and cites riddles from hundreds of different cultures including Finnish, Hungarian, Native American, Chinese, Russian, Dutch and Filipino sources amongst many others. Riddles have been characterized as one of the most important forms of oral art in Africa. 
In the assessment of Elli Köngas Maranda (originally writing about Malaitian riddles, but with an insight that has been taken up more widely), whereas myths serve to encode and establish social norms, "riddles make a point of playing with conceptual boundaries and crossing them for the intellectual pleasure of showing that things are not quite as stable as they seem" though the point of doing so may still ultimately be to "play with boundaries, but ultimately to affirm them." A perfect example of this is the Riddle of the Sphinx, arguably the world's most famous riddle (indeed, I cannot begin to tell you how many times children have given it in an attempt to stump me). 
The Riddle of the Sphinx is: What is the creature that walks on four legs in the morning, two legs at noon and three in the evening?
The answer is a human, because a human being walks on all fours in early life, on two legs as an adult and with a walking stick in old age. Of course, arms and canes are hardly legs, but they functionally act like them, thus proving Elli Köngas Maranda's point. Also and on a side note, Sphinxes are famous in world mythology for their riddles – as well as their annoying habit of killing those who fail to answer – making them a sort of mascot for the art of riddlery.

When people ask how I fashion riddles, this is the answer

According to Archer Taylor, "the oldest recorded riddles are Babylonian school texts which show no literary polish," such as the riddle:
My knees hasten, my feet do not rest, a shepherd without pity drives me to pasture = ? 

I, personally, disagree with him as, per my own Riddle Maker mind, I judge the above riddle as perfectly respectable. My only grievance is that the answer was not preserved! AUGH!!

"Eyes see only what is possible. A trained mind can explore the impossible." - Magic: the Gathering

"The worthy shall cultivate a nimble mind to perceive the glorious wonders that await them." - Magic: the Gathering

Types of Riddles:
Experience has led me to the conclusion that there are four basic types of riddles: Logic, Wordplay, Scenario, and Combination.

Logic The most common form of riddle; generally describes something in a new way that, while telling the truth, makes it difficult to guess what the thing is.
Example: A box without hinges, key, or lid, yet golden treasure inside is hid = egg

Wordplay Less common but still widely used (and very hard to make), wordplay riddles are generally words puzzles that often have the answer somehow concealed within the riddle.
Example: When you take away some of me, I remain whole = Wholesome

Scenario Still common, at least among kids, but of a very different makeup. Typically they are a description of a puzzling situation and the person trying to solve it must figure out how and why it occurred. (This is the one type of riddle I do not deal in; too cumbersome to make and solve, in my opinion).
Example: A man leaves home. He makes three left turns. He returns home and finds two masked men. Who are the masked men? Answer = The umpire and the catcher (i.e. the man is playing baseball)

Combination A riddle that combines the principles of any of the aforementioned types.
Example (Wordplay/Scenario): One (k)night, a king and a queen went to bed in their room. No one came in and no one went out. In the morning the king and the queen were tied up. Who tied them up? Answer = The knight (this riddle for obvious reasons requires being told aloud rather than written)
Example (Logic/Wordplay): ---- (Sorry, but I am going to keep these to myself. Torturing people with them is too much fun to spoil by posting the answers here.)

? There is, actually, a fifth (and not so basic) kind of riddle; but you will need to visit the College of Caithnard if you want to learn it.

"A riddle is nothing more than a trap for small minds, baited with the promise of understanding." - Magic: the Gathering

Riddle ranking-system:
Doing anything for years naturally leads ones to take measurements of skill-requirements needed for certain level, so just as chemistry is considered a harder form of science compared to others, I measure my riddles per these ranks:

Easy Simple riddles that have a token of complexity but can be solved fairly quickly by 1st graders. These are always (at least for me) Logic riddles.
Example: When alive I am green, when I die I am brown, when I live I stay up, when I die I fall down = leaf

Middle-ranking The most common level of riddle and, for me, the easiest to make. Sophisticated enough in wording, playing with words and logic, to pose a challenge to most for several hours. I typically use these to judge a person's (3rd grade to adult) skill in riddle-solving. Most tend to be Logic riddles.
Example: What can’t you keep until you give = a promise / your word

Hard Difficult to describe this level as these are typically a short step or two above Middle-ranking, being of more complex wording and often having slightly less obvious answers. Indeed, those only one step (as opposed to two) above Middle-ranking I call Upper Middle-ranking. Both Logic and Wordplay riddles are common. (For clarity, I judge the example below as a pure Hard riddle as opposed to an Upper Middle-Ranking one.)
Example: You saw me where I never was and where I could not be. And yet within that very place, my face you often see = a mirror reflection

Riddles in the Dark; one of the Fantasy
genre's most iconic riddle games. I judge all
of Tolkien's riddles to rank from
Upper Middle-ranking to Master.
Master Few and far between are these riddles, both in terms of people able to make as well as solve them; even I have very few. As the name implies, only true master riddle-solvers can answer these, and often only after hours of thought, for they require one to truly think outside of the box. As a rule, I only pose these to experienced riddle-solvers: people who have successfully answered many Middle-ranking riddles at minimum. Both Logic and Wordplay riddles are common, though I would deem Logic a tad more so.
Example: ---- (Sorry, but I am going to keep these to myself. Torturing people with them is too much fun to spoil by posting the answers here.)

Grandmaster Answering one of these puts you in the riddle-solver hall of fame. Always Combination riddles (at least all of mine are), these can be counted on the finger of one hand and are hardly ever solved even by those who can answer Master-ranked ones. I have one myself and, though I have given it to hundreds of people over the years, only fifteen have ever solved it (and most of them took a few days to do so).
Example: ---- (Sorry but, as a rule, usually, it is never given unit a person or group has proven themselves at the Hard level at least, preferably with one or two Master-ranked ones under their belt as well.)

Championmaster Those insane riddles that are a hair's breath away from being unsolvable. I honestly do not know why I even bother listing this as a rank as, to date, my single riddle of this kind has only been solved once: by then-in-middle-school siblings Chloe and Heather, each of whom individually was a master riddle-solver and it took them, working together, a full week to solve it. In fact, I only created the Championmaster riddle because my friend Devin, who had solved the Grandmaster, challenged me to craft a harder one.
Example: ---- (Sorry, but today I only tell this riddle to those very select few who solve my Grandmaster.)

Riddle Mastery:

Now one often hears the term riddle master used to describe those who excel in the art of Riddle Games. But I judge the title differently because, while I have often been called a riddle master, I, paradoxically, am atrocious at solving riddles myself. Hence I say that there are two kinds of riddle masters: the riddle-solver and the riddle-maker, the latter of whom creates riddles. One can be both, of course, but if not, then it is the riddle-makers' task to train the riddle-solvers' in answering, and the riddle-solvers' task to challenge the riddle-makers' in creating. 

I, of course, am a riddle-maker and have trained all those interested in both the skills of solving and making – for to be one allows a unique perspective as to the other and, in my experience, riddle-makers are the rarer of the two kinds of Masters. That said, and also paradoxically, it is easier to learn to become a riddle-maker than it is a solver. Why else would I, after over a decade, still be terrible at solving?

As to the question of how one becomes a Riddle Master, the answer is, like with any title, the ability to back it up. For riddle-makers this is comparatively easy as one need only produce one’s list of created riddles; for example, no one has ever questioned my claim to the title once I show them my Riddle Sheet with 300+ riddles and their answers. As for riddle-solvers, they need merely demonstrate their skill by correctly answering the lion’s share of the riddles posed to them and/or by having a riddle-maker grant them the title. I say “and/or” because situations vary. What happens when someone who had answered few riddles correctly manages to solve several Hard and even a couple Master-ranked ones? This sounds improbable, yet I have seen it happen. What do I do? It varies. But I do know that I grant for all to hear the Master title on anyone who solves my Grandmaster Riddle, for obvious reasons.

How might a ferryman leave his boat, yet leave the ferry operating = ?

Here is a hint, provided by Neil Gaiman: only tell the ferryman the answer from a safe distance.

Riddle-Maker Philosophy
It occurs to me that Inquiry Teaching is synonymous with my Riddle-Maker Philosophy. To expand young minds, those minds must find the answer themselves and with limited hints.
It can either be found by, or given to you, when found you understand it, when given you might not = ?

Designing a curriculum is also akin to making a Riddle; working backwards, first you think of what you want to teach and then how to teach it.
As Patricia A. McKillip, author of The Forgotten Beasts of Eld and The Riddle-Master trilogy says, "When caught between the riddle and its answer there is no freedom," which is exactly why Inquiry Teaching has proven to be such an effective method of teaching children (who, in my experience, are the best riddle-solvers). Furthermore, not only are children typically the best riddle-solvers, they, at least in my experience, more often than not become addicted to them and subsequently develop great respect for the riddle-maker.
A riddle is a tale so familiar you no longer recognize it
Personal History and Methodology
All this may seem like a lot of categorizing, but trust me when I say that it is worth remembering. During my years working at summer camps, the campers fell utterly in love with my riddles and, in the way 3rd-5th graders will, took them and the systems/terminology I created for riddle-mastery very seriously indeed. Indeed, these terms and systems were developed while I was working at camps, gradually taking shape over the course of countless conversations with eager, curious, and earnest campers. What did you expect? That I was bored and so just sat down one day and started doing this? The only way to determine a riddle's rank is to test it, and large summer camps provide a very fertile field for doing so. Do this enough and patterns will emerge as one notes which riddles are solved most easily by the most number of people in different age-groups, and which ones are more challenging. I even have a standard starter riddle which I give to determine the potential skill of a person or group. Believe me, I may have made up the riddles for fun before doing summer camps, but my classifications and ranks evolved on the job.
Again, do not underestimate the impact telling riddles can have. They are marvelous ice-breakers if nothing else, and before one starts thinking about unhealthy competitiveness among children that leads to bullying and rivalries, the whole affair was always utterly light and cheerful. Friendly competition personified that walked hand-in-hand with cooperation, the riddles were a topic of conversation – a collective puzzle set by an adult with the campers bonding over the shared challenge and experience, building friendships off of trying to solve them, while interest beyond that is itself quite real. There was always at least one camper a session who ended up, on their own volition and without my suggestion, bringing a journal and pencil to camp to record every riddle & answer I had told thus far, keeping the journal with them to catch all the new ones until the session's end. Others wanted to learn how to make riddles, and collectively I spent many hours over the course of weeks helping these 3rd-5th graders become riddle-makers. One 3rd grader, a girl, created a Master ranked one that continues to torment people to this day. Truth be told, the only bad thing that ever came out of my riddles was that one particular group of kids one summer kept trying to steal my Riddle Sheet from my pocket.

Beyond that, there were other uses from a purely professional standpoint. Having an M.Ed myself, along with several friends and close relatives who teach upper elementary school, I can say with utter surety that every educator knows that that age-group tests their teachers, seeing how far they can push boundaries before their teachers reign them in. The interesting thing is that no camper ever tested me. Why? I assume it was because they were more interested in solving my riddles, and soon enough I was more than just another summer camp counselor – I was their friend whom they wanted to please. I know it sounds improbable, but there was one camper who was well-known enough in the camp that other counselors warned me before the session began that he was handful; and I saw why soon after meeting the lad. Yet he became so interested in the riddles that he never gave me more than token trouble and, in fact, spent much time trying to solve them with a group of boys. "When caught between the riddle and its answer there is no freedom," and that is how I taught: catching the campers between the two so that their own naturally inquisitive natures drove them not to push my boundaries but rather that which separates the riddles from the answer, the walls within their minds.
Above I gave two riddles. Here now are the answers.
What plays with words and logic, yet never tells a lie = a riddle
It can either be found by, or given to you, when found you understand it, when given you might not = the answer 
Therein lies the key points and pillars of both kinds of Riddle Mastery, to teach others to look beyond the obvious and outside the box by expanding their minds. It may sound overly simple, but I have seen young minds visibly grow and become more confident over the course of a mere two week camp sessions. The growth owed to the riddles gradually stretching and strengthening mental muscles, the confidence born from the accomplishment of solving them. A true accomplishment as I never give any real hints as to the answers; I only say what type of riddle it is, what rank, and whether the answer is tangible or intangible. That, and a few hours for them to solve it (after which I reveal the answer as to never tell would be cruel). I love the glow of triumph on people's faces when they solve one. Especially since literally everyone always at the start tells me that they are bad or terrible at riddle-solving. Well, 99% of those who tell me that in the beginning end up solving a few Hard ones at least. And with that confidence comes pride. Due to my ranking system the kids knew exactly how hard each riddle was, and could of course observe how many of their counterparts had solved it or riddles of similar rank. Honestly, they were as intrigued by the system as by the riddles themselves since they saw in it potential for greater challenges ahead and the chance to earn the coveted title Riddle Master. I know this sounds rather…unlikely, but the method lent to and supported itself. I got the kids interested in riddles by giving them middle-ranking ones, the solving of which gave them confidence and pride in this hitherto unknown skill of theirs called riddle-solving. Both of which lead to interest; hence they learn my system and rules, which leads to greater skill, confidence, and pride as they learn to solve increasingly more difficult riddles. The result? Towards the end of the two-week session they eagerly await me telling them Master ranked riddles, often badgering me to tell one sooner than I deem wise. (This is a key point, as giving Hard and Master rank ones too early will result in a loss of confidence since it is unlikely that the children will be able to solve them. Mental muscles are like real ones. Start with lifting smaller weights until you can handle the big ones.) The kids also learn more about themselves. I recall one group where a few realized they were notably better at Wordplay than Logic riddles, and vice versa for others. A fact that intrigued as opposed to upset them and prompted a healthy interest in the difference between the types of riddles (to say nothing of my Grandmaster Riddle that combines the two types).
Again, I know all this sounds absurdly simple and, from an educator's prospective, unorthodox, but it worked like a charm each and every time. I guess I am an unorthodox person to a degree, trying to find new yet no less effective while more fun ways to do things. Aldous Huxley once said that, "The secret of genius is to carry the spirit of the child into old age," while Albert Einstein noted that "If you want your children to be intelligent, read them fairy tales. If you want your children to be more intelligent, read them more fairy tales." I am not so arrogant as to name myself a genius, but I do try to live up to those quotes and employ them when educating. During lunchtime at camp I always chose to eat with the campers, even when I had the option to eat with other counselors. Part of it was because it is hard to hold a conversation when are campers running up to whisper a riddle-answer in your ear every few minutes, but mostly because I enjoyed it. Children have fascinating insights and by listening to them, by regularly talking to them on their level, I became their friend. (I also have some skill as a storyteller, so when riddles fail to quiet the crowd a tale succeeds. It got to the point where every lunchtime the campers wanted to hear a new story. Point of order, I was not reading to them; this was not story-time in the traditional sense. Like a Bard, I told them myths and legends I had more or less memorized and it enraptured them. On that note, I am well-aware that utilizing riddles in this way is not a good fit for many situations, but storytelling is much more flexible. I once worked at martial arts camp, and the parents knew me through their kids as the Instructor "who told amazing stories at lunch", their words not mine.) 
However, like any education methodology – if I be so bold as to call my riddling such – it relies on the passion of the educator telling the riddles; they must put their heart into them and be firm. I spoke above about 3rd-5th graders pushing boundaries, saying that because of my riddles they did not push mine. This is true, except for one detail. They pushed my riddle boundaries: “Can you tell me the answer, I promise I won’t tell”, “We need another hint; what is the first letter of the answer?” ect ect. They pushed me, but I did not budge and that, I think, helped me overall as a camp counselor; the kids saw that I was firm and unyielding regarding my own self-imposed rules of riddle-mastery, and so did not push me on actual camp rules. Interestingly, this is one of the reasons, I think, why they became so intrigued with the systems & terminology I developed. They saw how seriously I took my own rules and so took it seriously themselves. Whenever a camper solved a riddle they were supposed to whisper it in my ear so as not to spoil it for others and, if they were correct, I – after giving a hearty congratulatory cry of “Correct!” for all to hear – would instruct them to “give no hints and tell no one.” I know what you are thinking: Ian Adler, are you really naïve enough to think that not one 3rd-5th grader is not going to tell her or his best friend(s) or give out partial hints? Well, like I said, because I took the riddle rules seriously, so did they. Hence, in fact, not one camper ever disobeyed my “give no hints and tell no one” edict. Why? Not because they were afraid of my reaction, but rather because I had made clear that simply knowing the answer to a riddle means nothing. It is solving them that make the Riddle Master. In short, campers were not about to just give away the answer to a riddle that they had worked hard, often for over an hour, to solve. To use a different analogy, they took the riddle rules as seriously as the rules of a favorite sport or game and telling the answer amounted to cheating in their eyes. Also the ranking system alone kindled the interest of several, for telling stories of past kids who had attained the title Riddle Master made the current group want to emulate them and move up the ranks. Amazing how even friendly competition with others kids who they have never met and likely never will meet can drive children to improve.
By now many years have passed and my riddle-telling days at camps are generally over. Yet I look back and remember the joy I felt at expanding young minds with my unusual hobby, with my self-made riddles that FORCE people to think outside the box; and I remember the enthusiasm of those minds. How they would recognize and greet me jubilantly, campers a year or two older running and calling me by name and begging for a riddle – even recalling a few they had heard the previous year(s). How when I came back to visit one of the camps many of campers from separate groups had by chance been placed together, and how they cried aloud at my unexpected arrival. How first in high school and then in college I joined creative writing clubs, and my riddles became a standard part of the meetings. How in the summer of 2018 one of my old C.I.T. friends who was then a full Counselor wrote me and explained how much his campers loves riddles – that he had been using what few of mine he remembered – and requested that I send him my full Master Riddle Sheet. How I then weeks later got the same request from my old supervisor at a different day-camp. Riddle Mastery may be an unorthodox educational tactic, but it is an effective one that left a lasting impact. As I told my one of my old associates, “indeed, whenever I cannot tell them myself, it eases my soul to know that they are still being used to stretch the minds of and strengthen the bonds between young adventurers.” Truth to tell, it may be less unorthodox as opposed to simply a much older form of education. As aforesaid, Babylonian school texts employed it, and riddles were a respected literary form throughout the ancient world, even being one of the most important forms of oral art in Africa. It is only in the modern world that Riddle Mastery has fallen into disuse.
Now I can hear you saying, “this is all very interesting, Ian, but why did you start inventing riddles? You must have had a bunch already created before you worked at day-camps because otherwise you would have been unable to pose them to campers.” Quite right. As an avid fan of the Fantasy genre, I grew up with something of a fascination for riddles, courtesy of the iconic riddle-contest between Bilbo Baggins and Gollum. Hardly unique, true, and yet I soon ran into a problem: everyone knew Tolkien’s riddles. Then there was the Arthur show on PBS Kids, namely the episode "Arthur and the Big Riddle" where Arthur gets a spot on the gameshow Riddle Quest. These riddles were naturally of a simpler, albeit still challenging, nature (meant for sharp children to guess), and yet they only worked on the show because the characters did not know the answers beforehand from prior experience. I repeat, “did not know and could not look up.”
Therein lies the crux of the matter: Riddle-telling and solving had become meaningless because all riddles had become public knowledge or could be Googled in a heartbeat. Do you know how many people I told the Riddle of the Sphinx to upon first learning it? Dozens. All my friends. Do you know how many of them already knew it? Dozens. Most of my friends. Where was the fun? Nowhere, so I let my interest rot. Then, when I was around eleven-years old, came one of those ordinary days that ends up shaping so much more. It was a chilly Autumn day and I was sitting on the swing-set in the playground across the street from our apartment, talking to my younger sister and one of her friends who somewhere along the way had become my friend too. Then out the blue they asked me to tell them a riddle. So, looking around, I tried to think up a good one. “When alive I am green, when I die I am brown, when I live I stay up, when I die I fall down,” I said, and they swiftly got the answer: leaf. Yet it was a new riddle. They had never heard it before for I had literally made it up right then. Then they asked me for another riddle, I made up one for fire, and the cycle continued with me looking around for inspiration and racking my brain for ways to make the riddles rhyme if possible. Soon I had created just short of a dozen and, realizing that I would never be able to remember them all, went back inside and typed them all out on a sheet called Sayings and Riddles (for I also included all two my favorite quotes). Thus a new hobby was born: me looking around the house and nature for objects or concepts they would make good answers, and then devising (hopefully rhyming) riddles to match them. 
The years passed until I went to day-camp, not to work but as a camper, my group being for campers entering Grades 8–10. Naturally I had a good time, but then I must have asked one of my friends if they wanted to hear a riddle. In truth, I cannot remember how it began, but it ended with me – or rather the challenge of my riddle – as the center of attention. A trend that continued beyond that initial lunch period, but, being somewhat shy, I did not press nor embrace the role of riddle-teller despite the joy it gave me. That changed a year or two later when I signed up to be a C.I.T. at that same camp, and the rest is history as described above.
Still not convinced of the importance of riddles in education? See these below links and consider the fact that all agree how puzzle-solving is good for children and that a riddle is but a mental puzzle.
Beware another riddle master
OK, so maybe this is not all I have to say on the ancient art of Riddle Mastery or my own personal history regarding it...but it is most of it (besides, any true Riddle-Maker worth their salt always keeps an ace or two up her/his sleeve; or, in my case, in a hidden pocket). Finally, the reason why I do not post the riddles I make is because the whole reason I create them in the first place is so riddle-solvers cannot look up the answers on the internet. As such, to post them on Stars Uncounted would be counterintuitive.

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