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Ancient Wisdom for Modern Readers

How to Win an Argument: An Ancient Guide to the Art of Persuasion

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All of us are faced countless times with the challenge of persuading others, whether we're trying to win a trivial argument with a friend or convince our coworkers about an important decision. Instead of relying on untrained instinct--and often floundering or failing as a result--we'd win more arguments if we learned the timeless art of verbal persuasion, rhetoric. How to Win an Argument gathers the rhetorical wisdom of Cicero, ancient Rome's greatest orator, from across his works and combines it with passages from his legal and political speeches to show his powerful techniques in action. The result is an enlightening and entertaining practical introduction to the secrets of persuasive speaking and writing--including strategies that are just as effective in today's offices, schools, courts, and political debates as they were in the Roman forum.

How to Win an Argument addresses proof based on rational argumentation, character, and emotion; the parts of a speech; the plain, middle, and grand styles; how to persuade no matter what audience or circumstances you face; and more. Cicero's words are presented in lively translations, with illuminating introductions; the book also features a brief biography of Cicero, a glossary, suggestions for further reading, and an appendix of the original Latin texts.

Astonishingly relevant, this unique anthology of Cicero's rhetorical and oratorical wisdom will be enjoyed by anyone who ever needs to win arguments and influence people--in other words, all of us.

288 pages, Hardcover

First published January 1, 2016

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2171 people want to read

About the author

Marcus Tullius Cicero

8,254 books1,902 followers
Born 3 January 106 BC, Arpinum, Italy
Died 7 December 43 BC (aged 63), Formia, Italy

Marcus Tullius Cicero was a Roman philosopher, statesman, lawyer, political theorist, and Roman constitutionalist. Cicero is widely considered one of Rome's greatest orators and prose stylists.

Alternate profiles:
Cicéron
Marco Tullio Cicerone
Cicerone

Note: All editions should have Marcus Tullius Cicero as primary author. Editions with another name on the cover should have that name added as secondary author.

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Displaying 1 - 30 of 86 reviews
Profile Image for Srividya Vijapure.
219 reviews325 followers
February 9, 2019
Excellent primer on Cicero and Classical Rhetoric. While the book does quote passages at length from Cicero's books, it is an interpretation of his principles on oratory and rhetoric. Extremely interesting and Simon Vance does an excellent job as always in making me want to keep listening to him forever.

The examples or passages used are mostly from the trials but the basic rules are those that we can apply anywhere and to any kind of discussion or argument, which makes it a book that can be read and profited from by one and all. In fact, I would recommend it to all as it is extremely readable and fascinating. As for me, I know I will keep coming back to this one whilst also going onto reading Cicero's original works.
Profile Image for Massimo Pigliucci.
Author 82 books1,131 followers
May 13, 2023
Want to learn how to persuade others? This Princeton Press collection of Cicero's writings on the art of oratory, translated by James M. May, will do the trick! Oratory nowadays is both denigrated and not practiced, both of which attitudes are detrimental to society. After all, a lot of what we want and need in life, both private and public, is to persuade other people to think or act in certain ways, so oratory at all scales is fundamental to human intercourse. Moreover, we could certainly use the kind of approach to the art that is recommended by Cicero. For him it isn't just a matter of stringing together a bunch of empty-but-good-sounding words, as many politicians and salesmen do these days. Rather, effective oratory requires actual mastering of a broad scope of disciplines, as well as the deployment of logical, evidence-based arguments as one (but only one!) of its key ingredients. Think of it as virtuous oratory, instead of sophistry.
Profile Image for Julian Worker.
Author 41 books425 followers
January 1, 2025
This is a useful book for those interested in public speaking and I wondered when reading it how Cicero would have fared in a Toastmasters group.

According to Cicero, rhetoric is an art and not a science. He emphasises the need to practice the art and find out what type of rhetoric suits your nature, your voice, and your natural gifts as an individual. He also indicates the need to know your audience and the importance of being able to memorise the speech if necessary. Many skills are required in order to be a persuasive and eloquent speaker.

Finally, prior to even practising the speech, it's so important to be able to write the speech. Cicero says the pen is the best and most eminent teacher and creator of speaking.
Profile Image for 'Izzat Radzi.
149 reviews65 followers
November 11, 2018
You know what they say of classics!

It's regretable that I haven't read Aristotle Rhetoric before this.
It's a privilege if one is able to read Latin, because the English part is only 140 pages, with the remaining is in the original language.

Love the sub-chapter on the notion of memory and writing speech in helping oratory.
Though, the best for me, and this is significant throughout the book, is the Chapter : The Value of Imitating Good Models of Speaking; and Background Knowledge of oneself.

This two, personally affect me in the deepest sense, as two of five people who deeply influenced me are well-versed in the skills of oratory.

First, is in the build-up of the 2013 General Election.
I'm grateful that I -as a media unit (where from there I developed my interest in media studies) -had the chance to accompanied one student leader, amongst many others, in leading the political and the neglected citizens issues; from only dozens of spectators to hundred of thousands, inter-state roadshow to students societies meet-up.
Cicero himself trained under two renowned orator in his budding years, while in later help train one as well.
Seeing his action first hand and learning, it is as Cicerio suggested, to one who wish to learn must accompany (Arabic :mulazamah) a teacher for some time.

The second and most recent is in UK, a senior also I looked up to and deeply respected.

In his style meanwhile, one can see his profound reasoning and speech delivery as he accumulates amass background Knowledge and apply Aristotle's Method of Persuasion in argumentation.
When he argue -and he rarely does- it is not uncommon to see people were put into absolute silence!

Definitely need to learn and practice more.
Profile Image for William Schram.
2,280 reviews95 followers
June 25, 2019
Everyone in Ancient Rome was expected to be able to argue persuasively and give well-formed arguments. However, even by those standards, Marcus Tullius Cicero was a master of the craft. As such he wrote extensively on the Art of Rhetoric and several other subjects. He lived through troubled times in the Roman Empire and was eventually murdered for his political views.

How to Win an Argument chooses a small piece of Cicero’s work that mainly focuses on the Art of Rhetoric and Oratory. So we learn about the methods necessary to form arguments and the different aspects of a good argument. The book is selected, edited, and translated by James M May. I have not heard of the man before, and I don’t have any preconceived notions of what sort of voice to give Cicero. Therefore, I find his translations to be adequate. I can’t read Latin and I don’t feel like learning to do so.

The book doesn’t really flow all that well. I say this only because of how it is edited; it jumps from subject to subject. First, it starts with different types of arguments: logos, ethos, and pathos. The book is really exhaustive. The translator/editor provides some background to the entry and then goes on to translate Cicero’s take on it. I say it is exhaustive because it also contains the original Latin text and a summation of Cicero’s points.

I enjoyed this book. It was and was not in-depth at the same time. The inclusion of the Latin Text makes it somewhat better, so if you can read Latin, maybe you can try to translate it yourself.
Profile Image for Illiterate.
2,599 reviews48 followers
June 28, 2021
Extracts from Cicero on rhetoric. (This PUP series reprints widely available ancient texts under snazzy but misleading titles.)
Profile Image for Petrina Binney.
Author 13 books25 followers
September 2, 2019
When I was in my mid-twenties, a friend bought me a metal sign to hang in my house. It read, ‘I don’t need other people around to have an argument.’
She knew me so well.

I will say, for those who might think this book is a guide to winning any argument - it is, but under very specific circumstances. There is no winning one-liner to finish the opposition and have them scurrying back to some unknown spot, for a vigorous round of wound-licking, contained within these pages.

In fact, what Cicero does is break down every aspect of a good speech - whether it is used for a summing up for the jury, or a difference of opinion with a friend. A great speaker must have some natural talent, the ability to sprinkle some glitter on his words, and charm. A great speaker must practise his skills in order to make his performance flawless. He must have a world-beating memory, a working understanding of any number of subjects - not limited to the one he is speaking about, but encompassing pretty much everything that may or may not come up. Each of the skills a great speaker must possess would take a lifetime to learn, and there are many of them to master.

I would have thought this book should be recommended reading for every would-be lawyer, politician and business leader in the world. I’m not any of those things but, now that I’ve read the book, I suppose anything is possible.
Profile Image for Jon.
1,423 reviews
April 3, 2019
We live in a time when I guess the main rule of argument is "If a guy is an idiot, you're doing him a favor to tell him so." This entry into the Princeton U. Press series of selected classics (mostly Cicero and Seneca) is perhaps the least interesting except to students of rhetoric. For them it is a well-designed summary of Cicero's views, excerpted from works he wrote from the age of 17 to shortly before his death. The editor introduces each excerpt with his own explication, sometimes almost as long as the excerpt itself. The book is possibly the handiest introduction I've seen, breaking the parts of rhetoric into invention, arrangement, style, memory, and delivery, with subcategories and further explanations. Really more for legal or debate-form argumentation than discussing politics with your crazy uncle over the dinner table. Much of it is common sense, but the analysis and organization is amazing. I'll admit I had a hard time differentiating between the examples of low, medium, and high styles of delivery, possibly because they don't translate well, possibly because all of them were higher and more formal than anything you're likely to hear today.
1 review
August 8, 2021
A fun read, but felt that I already knew most of what was in the book as it seems obvious. Also, the book is more about "how to do a speech" than how to win an argument.
Profile Image for Steven.
98 reviews3 followers
May 20, 2025
If you're interested in learning about rhetoric from classical authors, this is a great place to start. May's selections from Cicero's works along with his comments do a great job of giving a digest of the Roman author's salient points about how to be a good orator.
Profile Image for Joshua Lister.
146 reviews10 followers
July 7, 2018
This book is a collection of excerpts from Cicero’s writings which are translated and compiled by James May. He also includes helpful introductions to each section. The organization is superb.

This is a quick and easy introduction, great for anyone new to Cicero or Classical Rhetoric. It also serves as an excellent companion to Rhetorica Ad Herennium. Ad Herennium is a text book written in the Roman rhetorical tradition and May’s compilation shows examples of Cicero putting the content into practice.
Profile Image for The_J.
2,056 reviews5 followers
January 16, 2021
In a tome of wisdom, I think that the best was to move a jury or audience reflect their essence so that you are moved by the message. In addition this pearl: If we consider our leisure time, what can be more pleasant or more properly human than to be able to engage in elegant conversation and show oneself a stranger to no subject?
Profile Image for Lamis Akkad.
104 reviews16 followers
November 23, 2024
Interesting book. Enjoyed the narration. It is clear that we can see much of the described principles and rules currently in application in modern court proceedings. Listening to it, though, as an audio book, was a bit less effective for me to retain the information. Otherwise, it was a nice listen.
Profile Image for Alex Pizzoni.
7 reviews
August 2, 2019
Interesting book and includes quotes from the time of Marcus Tullius Cicero; excerpts from stories are shown to help in winning arguments. I found it a hard read and the last 1/3 of the book has scripts from stories in Latin.
Great for someone who is an avid reader of classical civilization books.
Profile Image for Heather-Lin.
1,087 reviews39 followers
November 17, 2021
Oh excellent!

I quite enjoyed the brief overview of Cicero's life, as it gave context to the culture and government he was operating within.

I also enjoyed the exploration of the different levels of making a convincing argument: logically, ethically, emotionally. I didn't expect the examples of him arguing as an attorney to be as engaging as they were. There was one case in particular - a murder plot that sours and the intended victim was accused of murder himself - that had me completely riveted!

There was also a brief reference to seeking out mentors, and cultivating a robust memory using the mind palace technique.

Overall, interesting as well as still relevant. And the audio narration by Simon Vance is as always superb.
Profile Image for Mitch.
32 reviews15 followers
October 31, 2016
I picked this book up on a whim at an art museum gift shop. In my haste, I didn't realize that only around 130 pages were in English, and the rest in Latin. Still, this was a very interesting read and it was well edited and arranged. I'm happy to have it on my shelf for future reference, or if I ever decide to try my hand at Latin in the future.

I found it interesting how many of the topics covered felt like "common sense". How to arrange an argument seems like something most of us learned actively or passively at some point in school- but much of those fundamentals date back to the ancients. It just goes to show how much the ancients have influenced our lives and education!
Profile Image for Ricky Mikeabono.
576 reviews1 follower
January 8, 2019
This is a book of lies.
First, it is not written by Cicero. It is written by some guy named James May, who periodically references and quotes Cicero. If you want Cicero's version, go straight to the source and read the translations of De Oratore and Orator.
Second, it is not about winning arguments, it's about giving speeches. Organized, prepared, speeches in front of large groups. There's a very real distinction there. For a book on actual arguments, and everyday rhetoric, I'd suggest "Thank You for Arguing."
What a disappointment! Don't waste your time.
Profile Image for Richard Mulholland.
Author 7 books64 followers
October 27, 2021
You can't beat the classics.

In this case that isn't hyperbolic, this was a fantastic listen. So good in fact I have immediately bought the Kindle version to make more notes.

---

Just finished the second reading of this as I wanted to be more intentional in my learning than you can with audio.

This should be required reading for everyone. It's so good.
Profile Image for Tarek Masri.
9 reviews1 follower
June 10, 2020
This book is a great collection of selections from Cicero's works regarding the art of rhetoric. The editor's choices and the connections he draws between them make up a very connected and fluid continuity; it feels like the book was originally written as a single text. This makes the text very accessible and easy to read.

The editor uses actual anecdotes and speeches delivered by notable ancient orators (mainly Cicero) to highlight different aspects of the art of rhetoric. These increase the historical value of this text and make the text an effective window into the courtrooms and courtyards of ancient times. Cicero is famous for being one of history's greatest orators, so these speeches and anecdotes are mostly very interesting to read. The actual content of the book is nothing spectacular though, so do not expect detailed or unusual strategies. In retrospect, most of the information would seem "obvious", since the book mainly covers the general aspects of proper speaking and writing that have found their way into modern language and philosophy education. However, the historical value and the fluidity of the text make it a nice read, nonetheless. The rest of this review is dedicated to a general outline of what Cicero covers in the selections found in this book, for those interested:

The book highlights Cicero's views regarding the importance of rhetoric and outlines the different "canons" of rhetoric; i.e. of proper persuasion and oration. It starts with what he calls the "invention" of proofs, which can be either non-artistic or artistic proofs. The latter type falls under one of the 3 Aristotelian modes of persuasion: the logos dealing with facts (involving induction and deduction), pathos dealing with emotional appeal, and ethos dealing with ethical appeal (winning over the audience through character).

The next stage is that of arranging our proofs. The famous arrangement used in philosophy is outlined here, with an introduction, presentation of arguments, response to potential counterarguments, and finally a conclusion.

The next stage is that of style, which focuses on correct use of language, clarity, distinction (use of figures of speech, etc..), and appropriateness. Appropriateness involves choosing the scale of the "speech", its tone, and its overall approach in a way suitable to the context and audience.

Next comes the stage of memory: memorising the speech. Though this is not as important in modern times (as mentioned by the editor), it was a key skill for ancient orators. The editor includes some of Cicero's tips for developing our "artificial" (as opposed to natural) memory. These tips include the use of mnemonics and writing our speech down.

Finally comes the stage of delivery. This stage deals with how a speech is delivered in terms of voice, facial expressions, gestures, and overall body language. Cicero regarded this stage as extremely important, since great content needs proper delivery to reach an audience, while dull content can be masked with great delivery.

The editor concludes the book with Cicero's views on general traits an exceptional orator must have, most importantly being well-rounded and knowledgeable in all the liberal arts.
Profile Image for Brad Balderson.
31 reviews18 followers
October 3, 2020
This is a good book - so why 3 stars? The reason is because it could have been GREAT.

I learnt a few important things from this book - the most important being the relationship between writing, reading, and speech. Cicero believed - and practised with great success - that writing is the gateway to better and clearer articulate speech. He also believed that - while being aware of and familiar with pedagogical rules of rhetoric is somewhat helpful - the foremost important thing was to actually have knowledge. Anyone who has written anything or tried to explain something will know that the difficulty lies in what you DON'T know- where you get caught up, where you fumble - THAT'S where you lack understanding - as Richard Feynman taught us. Cicero also figured this out. Therefore, to truly be able to speak and to write you need to understand - but the best way to understand is to and explain. So it follows - like any other skill - the capacity for persuasive writing and speech comes as a natural result of dedicated study, practice, and reading across a wide range of subjects.

Cicero also discusses the rarity with which this faculty - the faculty of speech and persuasive written word - develops. He discusses that the reason is few people studying for understanding. He also discusses the necessity for mnemonic techniques in order to remember vast amounts of information, and also the power of speech for both good and for evil (both Hitler and Churchill were great Rhetoricians).

The final important thing - which was mentioned quite early in the book - is the iterative creation of persuasive argument. First there is invention, then arrangement, then style, memorisation and delivery. There is also discussion of the different techniques of rhetoric - the Ethos, relying on the ethical character and trust in the orator as a means of persuasion; the Logos, persuasion through the logical cohesiveness of the argument, and the Pathos, persuasion through the appeal to the emotions and passions of the audience.

The reader of this review can see perhaps how profound and powerful the above ideas are, and how they clearly only just scratch the surface of what is clearly an extremely important discipline of study - rhetoric.

This is why I think the book is only worth 3 stars - it barely scratches the surface; just as I was really getting into it, and was really excited for more - it ended. Turns out that half the book is the original latin text, so the book is actually not a book - but a pamphlet of 172 pages. Anyhow, you don't need to read this book - there is probably much better books on rhetoric which won't end having barely begun.
Profile Image for Misho.
30 reviews
May 21, 2025
Part 1 of Rhetoric: Non-Artistic Rhetoric: Using the facts vs Artistic Rhetoric:

Logos: using a logical argument
Weapons of logic to win arguments are to employ induction by the use of examples and deduction through syllogistic reasoning (fictitious or historical analogies). With the syllogistic approach you then induce a probable conclusion about the matter in dispute, and then offer a general or universal application drawn from the example. What this does is
1- presents one or more similar cases
2- states the point we want conceded
3- draws a conclusion that reinforces the concession or demonstrates the results which follow from it

Ethos: winning over the audience/presentation of character
Your character will help you make your point: your prestige, accomplishments, the reputation that you’ve acquired through your way of life. And these come across better if you have a gentle tone of voice and you show restraint and kindliness. If you come across as decent, unassuming, not severe, not obstinate, not litigious, not harsh, with goodwill, you will win over the audience when they see the lack of these qualities in others. Speaking with mindfulness and reverence to God speaks volumes to how you come across.

Pathos: Arousal of emotions in the audience
Bring out the heavy emotions in people. You should even feel inside what you want the audience to feel to know how to bring them there.

Part 2 of Rhetoric: Style - eloquence forms a unity in whatever realm it travels and it is persuasive
• Clarity and brevity
• Avoid ambiguous language
• Saying words with too little breath or too much emphasis
• Excessively long periodic sentences
• Spun-out metaphors
• Confusing chronology
• Mixing up people
• Distinction (ornamentation): using tropes like metaphors, figures of speech, figures of thought
• Sprinkle sweetness or flare a bit here and there but don’t rely on it, similar to how we like sweet foods at time but wouldn’t be able to strictly survive on sweets
• Appropriateness

Part 3 of Rhetoric: Memory to be able to recount or lay out the narrative
• Introduction: bring the audience into the proper state of mind, character helps here
• Narration or statement of the case
• Argument including refutation of opposing arguments
• Conclusion or epilogue

Part 4 of Rhetoric: Delivery
Is huge to drive home everything what you’re saying. It can all fall without it. Use gestures and facial expressions to drive home the point

Choose a good role model to look to for speaking. In the Roman times, people took apprenticeships for such. But make sure to prune out their flaws.

Writing is such a crucial component to speech that people neglect because it takes effort. Writing will help you overcome random speech by reflection and preparation, especially with diligent writing. Cicero learned a routine from Gaius Carbo where he would watch a speech and try to memorize as much as possible then redescribe it written in his own words. But he found a defect that he ended up copying words, so he changed this by watching Greek speeches and then transcribing in Latin

This entire review has been hidden because of spoilers.
Profile Image for Tammam Aloudat.
370 reviews32 followers
July 23, 2018
This is a translation of some of the work of Cicero, the greatest of all Roman orators, about the art of speech. Cicero was a man of humble origins who became with his words and his oration the Consul of Rome.

The book is a selection that aims to illustrate some of the technicalities of rhetoric in a way that can be easily digested and absorbed by the lay person. It tries to bring together some basic rules in almost a bullet point format and goes only in little depth in explaining them but then illustrates the points with passages from Cicero's own oration and speeches. So in a way this is the short summary by the translator/editor of how they understand Cicero's rhetorical principles. The translator did a great job putting it together... however, this would be a little too simplistic for anyone with any familiarity with rhetoric and the works of the Greeks and Romans on the topic and I find the structure of the book owes more to Aristotle than it does anyone else.

All in all, I think it is well done and a great introduction to rhetoric and winning an argument, an art that has survived for twenty-five centuries.
Profile Image for Volbet .
378 reviews20 followers
September 28, 2023
The book's title is kinda misleading. It's not so much as it is guide on how to construct an argument like a skilled orator. This short compilation of text snippets from will form a really good backbone in your future debates, speeches and litigations, but it won't teach you how to respond to counter-arguments or how to think on your feet during negotiations or debates.

So while you can definitely use these outtakes to write a very compelling speech, but once you encounter any resistance you're on your own.
Profile Image for Canuknot (Cyn).
26 reviews12 followers
November 27, 2019
Well done, this book is excerpts with commentary and interpretation from the original text by Cicero Rhetoric. Cicero (3 January 106 BC – 7 December 43 BC) was and is still considered one of the greatest orators in Ancient Rome. How to win an argument probably would have saved my ass numerous times if I would have read it in my proposing and presenting class in grad school instead of whatever I did to survive that living nightmare. Not only does this little handbook have helpful information about how to give a speech and avoid looking like an ant set under a magnifying glass in the hot sun, it’s another intriguing look into how the ancient people and civilizations thought and conducted their daily lives.

For the record, I’m still mad at Mark Anthony for Cicero and his family; fuck that trader, thank you Octavian.
15 reviews
September 6, 2020
Received this book as a gift. If you don't have much experience with certain modes of persuasion, the advice in this book--collated from one of the giants of "the canon" could be useful. However, if you've been exposed to any amount of debate-type training, or courses on persuasive writing, the insights distilled from Cicero may feel a bit basic. This does not reflect on the advice in this book by itself, just that the advice is so fundamental to western rhetoric that you've probably heard it in some other form before.

It's like watching an episode of a TV show from decades ago that was stylistically groundbreaking at the time and finding it derivative. It probably was groundbreaking! But its elements got integrated so deeply into the years of pop culture afterward that watching the source text feels repetitive.
Profile Image for Matthew van der Hoorn.
8 reviews
June 2, 2022
An exciting read, that's for sure. While it doesn't go deep into the points of Rhetoric, it's a great introduction to the field. My knowledge within the area is small, to say the least; this was the first book on logic and reasoning that I read... I assume that once I have more overall knowledge and skill within the faculty of rhetoric, I will be able to get more out of the translated passages of Cicero himself. Still, for now, I had to do it with the comments of James M. May and was able to get some interesting ideas out of it.
The title is a bit misleading because the book's unity, as Adler would call it, is not about winning an argument but rather about becoming an Orator; that is, a persuasive speaker. You can get the principles to win a discussion out of it, albeit not profoundly, but it isn't what the book is leading toward.

Profile Image for Nick.
Author 21 books134 followers
August 22, 2019
This is a gentle introduction to the life, works, and strategies of Cicero, one of the greatest orators and rhetoricians of antiquity. You don't learn a huge amount about any of those things; just enough to whet the appetite. But I imagine the author was strictly instructed not to make the book too difficult to digest. The only real failing of the book is that you don't learn how to win an argument. Instead, you learn a little about how Cicero went at it. But don't be surprised if times have changed, and so if you try Cicero's approach (of saying dark things about the personal lives of the people you're arguing with) it doesn't actually help much to win any arguments in the modern era. You might get a libel suit out of using Cicero's approach today, but not much else.
158 reviews2 followers
November 24, 2023
Much too short to have value. However it is still an interesting primer on Cicero and the power of Roman rhetoric. While much Cicero writes about is now common sense and very common practice - if you know anything about persuasion or debate. He does go to the root of the practice, however this book is not it due to its length, it is only a basic summary of argumentation, hardly a guide, and after reading it you will hardly get better at argumentation.

But perhaps it is a good introduction to Cicero? I prefer Cicero's the Republic and the Laws for that purpose. So I would not call it that either.

Interesting read however.



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