The Sorry State of SSL

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The Sorry State of SSL
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Hynek - The Sorry State of SSL Those web pages with shiny lock icons boasting that your data is safe because of “256 bit encryption”? They are lying. In times of mass surveillance and commercialized Internet crime you should know why that’s the case. This talk will give you an overview that will help you to assess your personal security more realistically and to make your applications as secure as possible against all odds. ----- The rule of thumb for people without degrees in cryptography on securing data on the Internet is “GPG for data at rest. TLS for data in motion”. And it’s actually a very good rule everyone should follow. The only kicker though is that configuring (and using!) TLS properly is not as simple as it sounds and if you’re not diligent as a user, developer, and ops engineer, you can easily compromise your data’s security despite best effort of everyone else. This talk will be multifaceted; you will learn: - how SSL and TLS roughly work and why their state is sorry, - server- and client-side duties for best possible security, - what alternatives you have for using TLS in Python, - things to keep in mind when configuring servers, - and what perils outside your control still can trip you up. In other words, the leitmotif is to show you the most common traps you should know about when using and deploying applications relying on TLS for transport layer security and how to avoid them.
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so I'm not tiny by but and you may know me from internet right like this and then
squatting most of the India consolidated around I other places you can you may know me from is here on
yes this I just there's the and your Python veterans and when doing that
and the infrastructure environment you notice small friendly and German posting company endowment constant it's a few transitions away from you the amplitude problem was solved
tell you middle shiny items that promise your safe because of military-grade encryption are life so on this
statement men may have been a bit more controversial a few years ago before Mr. Snowden's before its current onslaught of Mesozoic and again it's just like every week something new my those problems are much much older we have all the sorry state like 10 years ago nobody because they were just informal Hegel bearing ignorance deals with just there in all browsers always itself was open source software so what could possibly go wrong so the problem is that you really need to know how things fit in together and how everything is working in in order to assess the the risk because always risk and help to minimize the because you can do much more damage than any anybody can opens up every will if you just repeat some on popular mistakes that i've done every day so before we
get into those that that only link you will have to write down today from every other link every project every other concept will be there so on just now way back and relax and enjoy the talk and it'll start and runs
0 why is this so that the state of the so sorry and what it really is as and what the hell does it have to do with TLS and I think this question is best answer it would have for history lesson because everyone loves history lessons and all particle 1 starts in the mid nineties when let's get started thinking that it would be nice if entering the credit card number on the internet would not entail people buying drops out of the pocket and so they introduced as is L 2 which was completely hosed as the as the basis for HTTP as learning as the standing for secure not SSL on this fixed diverse marks a year later In this L 3 and the other 3 years later and after a brief of battle with Microsoft it finally became a true IETF standards and was renamed to TLS Transport Layer Security so just to reiterate as a cell is a product from Netscape from 1996 TLS is intrinsic to
15 years now so I basically executing here with the name but since everybody knows that iterations are always also and so I wanted to which everyone I could so I use the most used word so if I hadn't triggering yeah I hope you'll learn different thing today and will not say this is so in the future anymore so 2006 and 2008 the widely ignored kills 1 . 1 1 went with the release them both fixed of some serious problems that and really nice features but nobody can fast forward to last year where for some totally random reason people start scrutinizing or security had it's again it turns out what I found was not entirely good on so for example all browsers however supported only Telus 1 until 2013 so tails 1 from 1989 by the discoveries of 2013 changed everything on the times just saying it's something contains as PLS they did not have done so and you really need to know roughly what you're doing because this technology is really sharp edges still I hope this will change in any future but for now we will have to know what you're doing in the whole thing to get so what the h we want to provide you with so there's appeared entity using certificates you can verify we connect the hose with host is kind of some crucial trick you into connecting to their own server pretending to be you so that protects you against man in the middle or MIT in the text then there's confidentiality which is medically encryption of network traffic which means that people can't eavesdrop on your on your password secrets and it as what most people think about when they hear cryptography TLS SSL but if the it's only a 3rd because of the thing is integrity which ensures that you can detect if tls records gets lost mangled or multiple times which is just as important as other things so now we know roughly what we're working with let's see how to use those and explain for details along the way so after his departure will know what the smells of continuous usage are and what to avoid sorry servers and I
just know that I'm sticking to optimize itself throughout the rest of this talk because that's what you mean most likely using especially in servers and in europe . 0 speed more or less your duty to and sure the model
the best possible security for users because they can neither see nor affect your own set up so the 1st step is to use these halfway up-to-date software
and deploy anything this today we are being negligent lazy and doing so but and jobless assuming that you're using some distribution we'd back cost security patches because I was you that there's no way you use anything other than than very newest versions because the
emergence come up for a reason that especially for a muscle itself so if you compile yourself you have to stay on top of it unless you want a beating heart so the 1st
thing you do if our client connects you is that you send in your certificate which states rule or in order to climb a tree believe what you could say it has to be signed by a trusted 3rd party which is called certificate authority or that so this set of labels C h declined trust is called the trust of base and it's located either in a browser or analysis or in operating system depends which brother using or what software during using so to prove that this certificate spectra URIs because you're selling it to every sending although everyone who ever like a secret key belongs to each certificate which in turn is used for signatures which in turn can be verified using a certificate and so you can prove that our relation late in the possession of the secret or and stuff that you can be trusted with the certificate who have just sent to the client you
just now is to make Europe so certificate trustworthy because you TLS is worthless it around that there's no way for trying to determine who you actually are and you will not get a certificate signed directly by a trust that party but you will get a simple change file along with your certificate so for example in in this case the trusted 3rd stresses and trust signed some certificate for Okamoto which in turn science synthetic promoters certificate which in turn finally signed my certificate so whenever a client in this case is opponents of browser connect it will receive all 3 certificates and then figures out the path to secure so on they can be forgetting chain certificate is a typical rookie I'm sure the certificate is valid for a host name of restaurant and of course make shortages certificates are not expire because that's kind of embarrassing so that is and what 2 chances are it's not necessary but for for instance apples so as well was also see that while the heavenly suggesting that the points wasn't was sent is a good idea because it's not done to it if you don't have to support Windows XP you can also dropped as 3 and finally disabled chest compression to avoid from text the 1st and last usually inspection tour of muscle cells so you don't have to to do it yourself but you have to verify that it's actually happening so the next objective is to come from Europe Europe disafforested such that every client is the best possible encryption and surface it is just a of various on cryptographic primitives that I used to secure a connection and ultimately the server has the last say which 1 is used so uses powerful good I will start with and themselves because they use to explain just imagine them as black boxes that they planted the in and secret key and but gives you several texts that which should be in this is indistinguishable from random data so she'll of symmetric that means that if you want to be criticized takes the role of and function of the Cypher is exactly the same this will be important on a does pretty much straightforward is a bit more complicated the cows most services a block oriented and means that operate on a certain block size usually 128 bits so you can just put a 1 D government into it and wait for esthetics succumb also on other and is that the data is a bigger give Tobin up and even smaller the patent so the practice usually do both on home the most common way to do this is nowadays still of so called sigh from what training or CBC which unfortunately has been implemented very ridiculous which is total similarity of detection problems the beast being the most famous 1 so then the fixed until someone 1 but you may remember what people that kills 1 ignore it so other alternatives which have been employed actually was classified pixels every every browsers full fixes for all possible box made being covers the rivers and streams of like policy for in the past and the church of 20 in the hope for the future and finally till some point to broader shiny new mode Caltech alot counter mode which does much more interesting and padding on more than 1 later so now we know what separated so which 1 to use and is a questionable of contention and the correct answer is nothing but a 1st thing some practical opinions I'm I'm going to say that the best current cyphers on 80 is 120 go what under mode and the streams of a church of 20 from Denver and and our AS GC-MS really really weird hardware and check on the on is really good software so ideally both and the decline decide which 1 to use which is exactly what google last unfortunately it's not available to us mere mortals yet so 80 s in and it is from but in 4
layers of finite brothers you still have a whole lecture 8 years CBC it's the same size purchase of different block mode and as completely fine until someone to so you don't trust in those areas using chips because they're vector where all agencies are you going to use this as a parasite model problem it's just yet it's a bit of this slightly slower but it's absolutely terrible on TLS 1 so I don't have really any choice here other than hoping that the client companies fixes for the most basic text so if you need to support engine clients like Windows XP I would just use it for the last which is decent so this and and that it's secure enough for 3 means that they do yes efforts used 3 times so you can imagine how on fast 1 and this so you don't need anything else that to support everything you may encounter on the net and the especially very of the following once exports diverse have been intentionally readings it in times when the exports of our cryptographic so the software from the US world of serious restricted to decipher 1st are make sure by design of also not of you anymore DS which is not as far as I know back door when it use 56 bit keys and that can be brute force some but much before and finally there's my favorite R for this just seems to be a bit more complicated but in reality it really is not why some people are still claiming that is suitable for all modes based problems all the most cryptographers I know that is just for years past for maybe flaw in ways that national agencies maybe able to the Critique so the and people with access to the service node a final confirm the suspicion last year so what it's fast the in order to and crude and decrepit suffers and the key another or established new semantics and so you need the same key for both operation so we need a way to on encryption keys already at the end of that I think it would be encrypted connections which kind of sounds like a chicken egg problem of fortunately nest and you and gives several ways this commission cheese or insecure connection without actually making them so 3 of them are currently wedding white and the prom most famous ones are a state which is not just a company that took several bags of money from an estate but also public key cryptosystem so yeah public key and a private key public key for encryption private for decryption symbol it is if I pick up some really like it but as soon as the secret key but he's out our server all future and past communications become plaintext protect we say that let's perfect for secrecy already is not and this is the 3 repeating it's 1 quarter or 1 once a a break in that is all it takes and such that the thief can decipher everything they've captured capture or ever will capture and there's no way for you to know whether this is happening but there's on the ephemeral Diffie-Hellman which is given as much slower if you were running wild people were reluctant to the point because fortunately now we have the CD-HIT which is both fast and PM convergence still not completely full widely supported under getting there will not do everything humanly possible to ensure perfect for secrecy for as many times as possible and I find it even more important than you using the right side for and for that you want to support both DAG and the Soviet and so the the DAG is faster I would suggest you prefer use our state only as a last option only have to finally
message of indication codes for max I used for message integrity so messages until is convex just means of TLS records a lot of data that you send out and received the report on the next are not just specific and they combined so magical to dust which share secret keys to ensure both integrity and the authenticity of the messages so we know that this exact message as we have all sent by the person who knows the shared secret key in that order and TLS uses a so called the hash Magritte H make when so you may also heard this term so maybe things up kind of polling place and before that as as you say something similar about different if you connections security traditional you can even define the function the hashing function you can that that is gonna use Florida h max and there's nothing you can read the wrong like dangerously wrong but I like to be stable and define h max because they earlier agreed it doesn't suffer from the usual under-five pollution problems like the 195 but it's in 5 and I like short separatists finally he also point to introduce the the possibility of this I 1st bring elements of indication and this is where of aforementioned GCM is interesting because this lot as a method of litigation both right in so it's not an additional operation it is handled within the hour encryption and decryption some finally if you list does not contain only strong give a 1st make sure to configure your server that is L 7 preferences and a higher priority expired does the most up-to-date TLS limitations on both sides 1 by you anything if the client sends a list of them with our SpeechEval best at the top and you begin to comply although you could have had charge of 20 or whatever future brings so there are actually don't with texts that can make such things happen so there basically not you would have told you on past flights you're fine convey ahead of the average everything else just illusion however you have to test your of your set up because this release computing stuff going on like on role 6 . 5 moles centers for of sentences for by that publicist that support the CD-HIT however the engine X has been compiled against all of masses which means that it's does not expose it to the clients so if you just look on the server and play with your site for strings you look impression everything is fine but from outside sexually not so it always have to test is system from the outside and if you just peachy GPS all which and got if you like because think just use the example as is ulcerative from on once and I'm going show just to show you the altered from my homepage and help you to just read the results and I would like to stress that the test many more things and what talk about I look and attack on time anyway but do the basics get back to that page and I'll make sure as we as much as of possible is green always came from past it's not that difficult so certificate as
I well it from my homepage both with and without a triple w it's village from this March until next May and the key is an artist they are for chaos the which means that it's users or estate for about 2 signatures not for key exchange is the same algorithm but completely different use cases different implications some other possibilities obvious as which nobody uses an easy you say it is gaining some traction but it's still under supported by both clients and associates so if you want to be on guard and deployed this year's a you have to pay a lot more for certificate and you have to do with all certificates set up like was doing right now so and forth Our state he's for case the occurrence to state-of-the-art so deploy new certificates you should aim for that 2 K is barely enough for most common right now 1 case a serious security problem so it was issued by commodity and this cycle would shut to which is is nice because again is what you should strive for most certificates analysis still sign shall 1 which has been deprecated you might so yeah it has like simulation because I think is just huge record to make lots of money and it's not revoked its trusted yeah protocols and ensure always chosen point to move from 1 2 and this is to inactive if Europe not a lot position like I am you have to keep as all 3 on let's see if you can drop it not finally forests from surface here is the currently best widely supported Cyprus strain and I will look at it in detail so it uses the fast and forward security achieved for of the exchange the location are safe for signatures which is the predefined by the certificate you cannot continue in yeah I decide for itself a 128 AGC amount nice nice and shot 56 images are shot to the other is used for she derivation on the head the tail handshake if there would be an external age so if you if he learned using GCM this function would also be used for all the will be used for a generic yeah so but this note that the service strictly prefers of for with security sigh 1st over known for for suggests 1 and in that sense that a certain certain preferred or this is really important I again if you can draw our say you want only useful to the old windows however it is not a privilege you for browsers we cast um compared to many mail service set ups and all Jeleva orphans I 6 can look like else dream so on your you have to look good words for you and what your plans are speaking of plants let's
talk about them but and it turns out the brothers side declines of TLS this inverse shape all of which is kind of surprising because they had only 1
single job verified verified certificate the
service since you is it valid or is it expires dusted trust value and finally this a certificate valid for for a host you want to actually connect to especially Jose limitations in such a pathetic state but there is an an actual scientific paper about how client software except brothers does not verify hosting unfortunately L has no real part is that is close so this evident frustration 1st thing is that certificate verification is all in and that's what have to to was explicitly which CAC you trust unfortunately trust source are highly platform-dependent every OS as it elsewhere fortunately there is an a function call that will that all properly configured computers the those that the full trust C from compiled and pack but for some odd reason this function is completely under amended in messes up I also inverted file and directory based on trust other bases so it will not work with Windows or 10 at least over the openness of the tube with West Ham so and as it always has else's obstacles very obstacles and on the operating system and decided to make our life even a bit more miserable by not installing them by default so make sure you install your seat your trust other bases before you try to use them so for free previously serious and as and for both DNN right had it's CA certificates that some consistency finally almost 10 you can either use Apple's engine developments as electricians and figure out the crux of their detection in contrast the relation agent which cos 2 weeks of my life or you built for the whole group which will give you a decent the the latest of mass itself at all insulation will create a copy of the system trust base and use that for an all the future of which and then it works with the API call mentioned before it's not perfect but it's it's about as good as it on fine for Windows there's there's or I see the of the of teams in year old and finally if you want to dodge the bullet completely you can just use certified which is a python package of what's lost trust other based on time it's kind of belongs to requests project but it has been externalized and now is on and the good support so but the so but also really like it when use your own interests of the base but if you don't have the knowledge and energy to figure out all these cases you may want to just way so also orientation as stated university and the problem here is because of Obama's just say so yeah but frankly absolutely no assistance from Obama whatsoever to verify that the certificate is valid for a host name nothing there isn't even any documentation on that because the just considered out of scope so whatever 1 so everyone has implemented on their own using our seas and but was advice from sector afloat and of course it's raining security backs and Python was involved to atleast 1 1 that I know of so but failing to verify certificates and host names has very grave consequences because it makes extremes visible to MIT text if you don't worry about anything which is the default behavior you don't anything special I can pretend to be you google it with a self-signed certificate I can created under a if you verify the certificate because you from somehow the the API calls but you verified
it the verified pulse name I consider you will because it's perfectly trust that I can use is just my own certificate from my own home page which will work out because it's perfectly trustworthy signed by trustworthy and CA but not for the whole system but you will not know because didn't look so verify
all the things it there's only 1 thing they move from this call Paul is that if you write TLS fine so they're always verify everything and any other way you're you're pretending to a level of security which is not just just there and the rest is just
1 day you limit your acceptable suffers the strong ones for times of 40 configured services and decimal there and is able to to that's all and if so if you do it it's a perfect storm of ignorance on 1 side and operating systems and almost all making unnecessary heart on the other and let's
continue but the user the weakest link security check because they can make everything fall apart no no matter how much the rest of the spectra so insecure and it started
fundamental misconceptions of use even once to do for you to for example it's nice sister connection to your chair e-mails arresting from the related in greatest side it's also keep doing it too much if the person you're talking to is connected to using a plain-text collections or some intermediate server this compromise yeah confidentiality level for his conversation is exactly 0 and since again there's no way for we to know where this is happening you always this universe TLS only for security between direct hosts you initially confidentiality for uh share an end to end conversations you will need an and particle like PGP for e-mail quality of checked and then there's the problem of some of the some data cannot be interested for example DNS security if you care so if you're surfing for example a job side adverse over HTTP S there's so many ways for it to find out that you're doing just that that traffic patterns the industry there's a lot of stuff going on that you cannot hide will have to use a VPN or something similar but any and roles all traffic through an iterative him again providers so that make sure that you trust them and this applies the more in strong to content delivery networks because the utility termination for you can see the traffic in clear text so in other words test sequences all your pipe passwords if they want to and this is another reason to never reused passwords because you never know what the party you may not even not know about gets to see that so next you are
cleared away something like this you may have been MIT and and the rules are pretty simple investigative warning and then use your best judgment so if the certificate is OK but expired have minutes ago it's time for such a treaty but you probably find it's mostly OK but you know the circumstances for example at the system doesn't properly support assigned 2014 you have you're probably find who I would avoid still circuitry because you might get to ticket of you are redirected to I guess is to use your mind if you if you don't fully understand what's going on here just climb man-in-the-middle attacks probably much easier than you think expression public networks all it takes is reduced the server so the next level of
thinking mindlessly is if some crook tricks something very good certificate into your trust sort of its because that means that every certificate is signed by this group Sierra will be considered trust with you by your system where you by your browser you will never ever see warning again when it might be a new and sometimes it's something images like on iPhone it's called profiles or something like that it is so low profile is you you can get some C a trusts changes to along the way and will not really know and you have to you that throughout the still a lot that can go wrong because the trust based isn't really under their control as you usually can have things but they usually don't remove things or maybe cantons things and there are some of estimated costs some level of discomfort so for example this means that the Department of Defense the United States of America consigned a certificate for any host mineral it'll be trusted and this is all the more things change it's right up there and just as everyone else every single country in the world has some CA they can be used for some for some of their and various reasons so and also number of C a being making fatal mistake mn heard of things like 2 weeks ago as Indian see a sort so deploying on global certificates or have forced to cooperate with the authorities and that maybe they're just corporations falls priorities may not entirely match yours for example Microsoft associate Google's associate whatever it means to you what this whole system just broke and speaking of broken let's look what Python but
simple rule of thumb as you see people off to screw up proteolyzed slave some of possible like metal tests sulfate would for you put energy from a put on a page in front of it there's a lot of information how can get it right those people in this of course is the stuff is just a properly reviewed probably that all lights is not true for some time and we do it just added some API calls because someone asked them about freedom but let's see any
way you want to do so we have basically 2 camps for GLS we have to solve the various is module and you have Pyramus itself unstoppable include the are pretty resting in everything before Python 3 . 3 and you do backward compatibility requirements the default behavior and 3 . 4 is still terrible so for example hosting the negation is still opt in of building code is there it can be active by default because people will cry because there barely deployed at Yale mistakes would break that's the situation you wish for Python through them because its coverage of as itself API so very very force for example it's impossible to write for secure servers so in other words you should never right servers with a standard libraries services when you before right in the country and those selected bunch of options they can disable of as to you you so disabled using compression stuff like this and then the problem is that you're bound to the open this cell of furor that your Python has been compared against so if you need a more recent of messes l and you will have to recompile you hold up I think we you hold I present a preacher but also completely missing from prior to its customer education but unfortunately it's on the IPI so there
is a way to do it for client software but hands up if anybody knew of that and I have actually used this year it was very few hands and 1 of their hands to implement it
biomass it comes from a time when a celebrity in support of the universe and what we have 2 points and then and it runs on all relevant Python versions and although it has been a bit dormant over a course of time it's still has a much much better coverage of the API stand and this is a module entitled to and more importantly you project gave a pile of myself and you like the after 10 years of Titus cryptography what is it is a bunch of life people with more time in some make for a better life decisions that came together to create a Python could delivery without guns but eventually the pattern cryptography authority or piker has ensured has been performed on an assigned for all that and is word see I bindings which of type friendly and what even nicer is that you can choose an alternative almost elderly problems of secure transport but make and are in the so we all get our heart bleeds and all our little fail in Python 2 ends what's really nice about the whole thing is that pile himself could just throw out all the seacoast if ever use it it's it's now occupies project which just this just building Python abstractions of he API that's coming from also so it gives some real momentum after language so years but again also occasion so again how this might be I service an entity will give you posted verification plus some more obscure race to verify the identity of a service which will probably never use but they are defined in RFC so various property and you have to remember to use it and will look now at
the most common frameworks and packages a whole well behaved killer citizens they are those
of with service again so you and let G 1 and G equal and later also the same problem the user study of libraries is someone you therefore they cannot have PFs I 1st they cannot set connection parameters tomato couldn't which theoretically on Python 3 but they don't G. U. and has some code in place of or maybe a crack in the next future but until then put an engine next from all of them this this was probably 1 of the few that had
reasons to come with the others in the 1st place because it's useful but implement all kinds of particles so I just GPS this always check marks out true only from 14 which was released a few months ago so it's useful for a favor and don't use anything all the elements that is that researchers with a nice with the
container so in other words you can deploy it appears that at some without putting anything in front of it and still have a specialist support and no 1 would get on twitter does not mean that you have to use called lexical CamelCase it's all the so there's finally Michael was our
assumptions that think so they just went and wrote the sums calling themselves and the man the mass of the of states and indeed the implementation appears to be out for featured but I would still always put originates in following but it's only because I have a general distrust toward using the C code and so should you to come finally make with notes and excellence of yeah so
it these figures on Wednesday as long as certain PET hasn't passed for as long as they don't support the Python 3 or 2 biomass itself so client
side even land you and just as bad as before but you can do better and to shows how they depend on certified and they depend on the back porch so are you get all the education budget for this so can't sensor default because they are the lecture before of 3 . 2 cells is a bit more complicated and all the low-level stuff is there since for you know so you can write rates of what's currently missing is a proper and want to do all of these by default but we getting there on thus never getting getting anywhere it's you through don't use it never for any HTTP and actions they just cannot get better instead use requests the guarantee 3 I what's really nice and request is that its price transparently to get the most out of it what you possible so they will used pay almost as if it's there and they will verify everything that's possible and they even our ship with 35 and so let
me say something which not to kill of if you can yes requests for a GPS queries the use of Pyramus cell In instance inside but right at your service and and if you need to know little tearless I strongly suggest to use pilot cancer cell because it's much better on Python through and it will follow you faithfully Python 3 finally use the pattern to some library only as the last measure only for clients and use the relevant but it's so
cropping up to throughout places soaring so it's sorry because people still say SSL there was been obsolete for 15 years it's sorry because the
implementation of terrible all
of them it's sorry because users run all the dysarthric take certificates mornings way and I didn't receive a 3rd party the long yeah but 2 peaks are 1 and those the parties that the
norm regularizer service from completely ordered software that is composed of your completely poorly clients from verify
anything although it's the the only job and we are talking about some obscure freeware here this generous secured sort of bioactive of found 40 per cent of tested banking apps to be assessed visible to MIT in the text and
sorry because Python is at the forefront of being terrible the current states really is the sorry the title of this talk is not the tension that others have look 1st be carried acceptance was the 1st step the TL support a much greater impact 3 and others in the past to improve
attractively in Python to so it's impossible to write secure but they the got the pike which is a bunch of really smart people + me and there's already adopted several cryptography related projects and it's supposed to be a one-stop shop for solid propo suffer for Python so we are really trying here but I hope always means recusal stop believing that love I can will keep you do not articulate certificate warnings B critical user conf years there was probably install security updates immediately if you connect the servers verify all the things and finally had was to get Python out of this mess the tools of graphics libraries report lots of fixing these parts this really a lot to do here and there so that's all I have for you today I hope you learn something and more importantly are if you to fix things now so go out
study that operates only inter and intra demands from media thank you