Why are secure programs so difficult to develop (for me)? - security

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Every time I work on a project involving passwords or securing data I get mired down into obscenely complex APIs and issues. I have not had much formal training in developing secure applications but I have not had much formal training in database, GUI, and build processes either. Many other areas of programming feel more intuitive.
Is security just a far more complex area than many others? I tend to think that it is not. Are security infterfaces and systems less mature than others? I would tend to think that there is a great deal of pressure for those systems to mature. On UNIX the 'trusted environment' was the norm until somewhere in the 90s. Is UNIX just suffering from its roots in this area?
Technology changes fast. Since I have been in school the computing world has become far more distributed and critical. Has security been dragged along for the ride as an afterthough? Are any new technologies promising? Are you suffering the same way I am?

Good security is hard, very very hard.

Apart of the considerations from the other answer, it is also because security is a balance between effective protection and effective ease of use. A system that is too complex to use due to its stringent security will likely to fail the user, which will drop it. Your role as a designer/developer is also to find the proper compromise between these two opposing forces, something which tend to introduce even more trouble.

I think that security is so hard because people feel inclined to do what they shouldn't, and try their best to overcome any barriers they find.
Only if this will power was used for something good...

Related

Using built in functions

I am developing a Windows Form Application in C#.I have heard that one should not use built in methods and functions in code since hackers have deep understanding of such built in methods and know how to fail them Instead one should always use his/her own functions and methods and if not then call built in functions intelligently from those newly made functions.How much is that true?
A supporting example in favour of my argument is that I have seen developer always develope there own made encryption algorithm like AES,DES,RC4 and Hash functions since they believe that built in encryption algorithm have many times backdoor in them.
What?! No, no, no! Whoever told you this is just wrong.
There is a common fallacy that published source code is more vulnerable to "h4ckerz" because it is available for anyone to spot the flaws in. However, I'm glad you mentioned crypto, because this is an area where this line of reasoning really stands out as the fallacy it is.
One of the most popular questions of all time on https://security.stackexchange.com/ is about a developer (in the OP he was given the pseudonym "Dave") who shared this fear of published code. Dave, like the developer you saw, was trying to homebrew his own encryption algorithm. Here's one of the most popular comments in that thread:
Dave has a fundamentally false premise, that the security of an algorithm relies on (even partially) its obscurity - that's not the case. The security of a hashing algorithm relies on the limits of our understanding of mathematics, and, to a lesser extent, the hardware ability to brute-force it. Once Dave accepts this reality (and it really is reality, read the Wikipedia article on hashing), it's a question of who is smarter - Dave by himself, or a large group of specialists devoted to this very particular problem. (emphasis added)
As a matter of fact, as it stands now, the top two memes on Security.SE are "Don't roll your own" and "Don't be a Dave".
While this has all been about crypto, this applies in general to most open-source software. The chance that a backdoor will get found and fixed goes up with each new set of eyes laid on the code. This should be a simple and uncontroversial premise: the more people are looking for something, the higher the chance it will be found. Yes, this applies to malicious users looking for exploits. However, it also applies to power users, white hat hackers, security researchers, cryptographers, professional developers, and others working for "good", which generally (hopefully) outnumber those working for "evil". This also implicitly relies on the false premise that hackers need to see the source code to do bad things. This should be obviously false based on the sheer number of proprietary systems whose source code has never been published (various Microsoft and Adobe programs come to mind) which have been inundated with vulnerabilities for years. Maybe having source code to read makes the hacker's job easier, but maybe not -- is it easier to pore over source code looking for an attack vector or to just use scanning tools and scripts against a compiled binary?
tl;dr Don't be a Dave. Rolling your own means you have to be the best at everything to succeed, instead of taking a sampling of the best the community has to offer.
Heartbleed
In your comment, you rebut:
Then why was the Heartbleed bug in openSSL not found and corrected [earlier]?
Because no one was looking at it. That's the sad truth. Here's the difference -- what happened once someone did find it? Now tens of thousands of security researchers, crypto experts, and others are looking at it. Suppose the same kind of vulnerability existed in one of the proprietary products I mentioned earlier, which it very well could. Once it's caught (if it's caught), ask yourself:
Could the team of programmers at the company responsible benefit from the help of the entire worldwide community of security experts, cryptographers, and other analysts right now?
If a bug this critical were discovered (and that's a big if!) in your software, would you be prepared to deal with the fallout caused by your custom implementation?
Unless you know of specific failure modes or weaknesses of the built-in methods your application would use and know how to minimize or eliminate them, it is probably better to use the methods provided by the language or library designers, which will often be both more efficient and more secure than what an average programmer would come up with on the fly for a particular project.
Your example absolutely does not support your view: developing your own encryption algorithm without some serious background in the domain and review by cryptanalysts, and then employing it in security-critical code, is a recipe for disaster. Even developing your own custom implementation of an industry standard encryption algorithm can present problems, and almost certainly will if you are inexperienced at it.

Is non-programmatic software development feasible? [closed]

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I'm currently faced with a very unusual design problem, and hope that a developer wiser than myself might be able to offer some insight.
Background
Without being too specific, I've been hired by a non-profit organisation to assist with the redevelopment of their legacy, but very valuable (in terms of social value) software. The development team is unlike any I've encountered in my time as a software developer, and is comprised of a small number of developers and a larger group of non-programming domain experts. What makes the arrangement unusual is that the domain experts (lets call them content creators), use custom tooling, some of which is based around a prolog expert system engine, to develop web based software components/forms.
The Problem
The system uses a very awkward postback model to perform logical operations server side and return new forms/results. It is slow, and prone to failure. Simple things, like creating html forms using the existing tooling is much more arduous than it should be. As the demand for a more interactive, and performant experience grows, the software developers are finding increasingly that they have to circumvent the expert system/visual tooling used by the content creators, and write new components by hand in javascript. The content creators feel increasingly that their hands are tied, as they are now unable to contribute new components.
Design approach: Traditional/Typical
I have been advocating for the complete abandonment of the previous model and the adoption of a typical software development process. As mentioned earlier, the project has naturally evolved towards this as the non-programmatic development tooling has become incapable of meeting the needs of the business.
The content creators have a very valuable contribution to make however, and I would like to see them focusing on formally specifying the expected behaviour of the software with tools like Cucumber, instead of being involved in implementation.
Design approach: Non-programmatic
My co-worker, who I respect a great deal and suspect is far more knowledgeable than me, feels that the existing process is fine and that we just need to build better tooling. I can't help but feel however that there is something fundamentally flawed with this approach. I have yet to find one instance, either historical or contemporary where this model of software development has been successful. COBOL was developed with the philosophy of allow business people/domain experts to write applications without the need for a programmer, and to my mind all this did was create a new kind of programmer - the COBOL programmer. If it was possible to develop effective systems allowing non-programmers to create non-trivial applications, surely the demand for programmers would be much lower? The only frameworks that I am aware of that roughly fit this model are SAP's Smart Forms and Microsoft's Dynamix AX - both of which are very domain specific ERP systems.
DSLs, Templating Languages
Something of a compromise between the two concepts would be to implement some kind of DSL as a templating language. I'm not even sure that this would be successful however, as all of the content creators, with one exception, are completely non technical.
I've also considered building a custom IDE based on Visual Studio or Net Beans with graphical/toolbox style tooling.
Thoughts?
Is non-programmatic development a fools errand? Will this always result in something unsatisfactory, requiring hands on development from a programmer?
Many thanks if you've taken the time to read this, and I'd certainly appreciate any feedback.
You say:
Something of a compromise between the
two concepts would be to implement
some kind of DSL as a templating
language. I'm not even sure that this
would be successful however, as all of
the content creators, with one
exception, are completely non
technical.
Honestly, this sounds like exactly the approach I would use. Even "non-technical" users can become proficient (enough) in a simple DSL or templating language to get useful work done.
For example, I do a lot of work with scientific modeling software. Many modelers, while being much more at home with the science than with any form of engineering, have been forced to learn one or more programming languages in order to express their ideas in a way they can use. Heck, as far as I know, Fortran is still a required course in order to get a Meteorology degree, since all the major weather models currently in use are written in Fortran.
As a result, there is a certain community of "scientific programming" which is mostly filled with domain experts with relatively little formal software engineering training, expertise, or even interest. These people are more at home with languages/platforms like Matlab, R, and even Visual Basic (since they can use it to script applications like Excel and ESRI ArcMap). Recently, I've seen Python gaining ground in this space as well, mainly I think because it's relatively easy to learn.
I guess my point is that I see strong parallels between this field and your example. If your domain experts are capable of thinking rigorously about their problems (and this may not be the case, but your question is open-ended enough that it might be) then they are definitely capable of expressing their ideas in an appropriate domain-specific language.
I would start by discussing with the content creators some ideas about how they would like to express their decisions and choices. My guess would be that they would be happy to write "code" (even if you don't have to call it code) to describe what they want. Give them a "debugger" (a tool to interactively explore the consequences of their "code" changes) and some nice "IDE" support application, and I think you'll have a very workable solution.
Think of spreadsheets.
Spreadsheets are a simple system that allows non-technical users to make use of a computer's calculation abilities. In doing so, they have opened up computers to solve a great number of tasks which normally would have required custom software developed to solve them. So, yes non-programmatic software development is possible.
On the other hand, look at spreadsheets. Despite their calculational abilities you really would not want as a programmer to have to develop software with them. In the end, many of the techniques that make programming languages better for programmers make them worse for the general population. The ability to define a function, for example, makes a programmer's life much easier, but I think would confuse most others.
Additionally, past a certain point of complexity trying to use a spreadsheet would be a real pain. The spreadsheet works well within the realm for which it was designed. Once you stray too far out that, its just not workable. And again, its the very tools programmers use to deal with complexity which will prevent a system being both widely usable and sufficiently powerful.
I think that for any given problem area, you could develop a system that allows the experts to specify a solution. It will be much harder to develop that system then to solve the problem in the first place. However, if you repeatedly have similiar problems which the experts can develop solutions for, then it might be worthwhile.
I think development by non-developers is doomed to failure. It's difficult enough when developers try it. What's the going failure rate? 50% or higher?
My advice would be to either buy the closest commercial product you can find or hire somebody to help you develop a custom solution with your non-developer maintenance characteristics in mind.
Being a developer means keeping a million details in mind at once and caring about details like version control, deployment, testing, etc. Most people who don't care about those things quickly tire of the complexity.
By all means involve the domain experts. But don't saddle them with development and maintenance as well.
You could be putting your organization at risk with a poorly done solution. If it's important, do it right.
I don't believe any extensive non-programmer solution is going to work. Programming is more than language, it's knowing how to do things reasonably. Something designed to be non-programmer friendly will still almost certainly contain all the pitfalls a programmer knows to avoid even if it's expressed in English or a GUI.
I think what's needed in a case like this is to have the content creators worry about making content and an actual programmer translate that into reasonable computer code.
I have worked with two ERP systems that were meant for non-programmers and in both cases you could make just about every mistake in the book with them.
... Simple things, like creating html forms using the existing tooling is much more arduous than it should be...
More arduous for whom? You're taking a development model that works (however badly) for the non-programming content creators, and because something is arduous for someone you propose to replace that with a model where the content creators are left out in the cold entirely? Sounds crazy to me.
If your content creators can learn custom tooling built around a Prolog rules engine, then they have shown they can learn enough formalism to contribute to the project. If you think other aspects of the development need to be changed, I see only two honorable choices:
Implement the existing formalism ("custom tooling") using the new technology that you think will make things better in other ways. The content creators contribute exactly as they do now.
Design and implement a domain-specific language that handles the impedance mismatch between what your content creators know and can do and the way you and other developers think the work should be done.
Your scenario is a classic case where a domain-specific language is appropriate. But language design is not easy, especially when combined with serious usability questions. If you are lucky you will be able to hire someone to help you who is expert in both language design and usability. But if you are nonprofit, you probably don't have the budget. In this case one possibility is to look for help from another nonprofit—a nearby university, if you have one.
I'd advise you to read this article before attempting to scrap the whole system. I look at it this way. What changed to prompt the redevelopment? Your domain experts haven't forgotten how to use the original system, so you already have some competent "COBOL programmers" for your domain. From your description, it sounds like mostly the performance requirements have changed, and possibly a greater need for web forms.
Therefore, the desired solution isn't to change the responsibilities of the domain experts, it's to increase the performance and make it easier to create web forms. You have the advantage of an existing code base showing exactly what your domain experts are capable of. It would be a real shame not to use it.
I realize Prolog isn't exactly the hottest language around, but there are faster and slower implementations. Some implementations are designed mostly for programmer interactivity and are dynamically interpreted. Some implementations create optimized compiled native code. There are also complex logical programming techniques like memoization that can be used to enhance performance, but probably no one learns them in school anymore. A flow where content creators focus on creating new content and developers focus on optimization could be very workable. Also, Prolog is ideally suited for the model layer, but not so much for the view layer. Moving more of your view layer to a different technology could really pay off.
In general though, 2 thoughts:
You cannot reduce life to algorithms. Everything we know (philosophically, scientifically) and experience demonstrates this. (Sorry, Dr. Minsky).
That said, a Domain-Specific tool that allows non-programmers to express a finite language is definitely doable as several people have given examples. Another example of this type of system is Mathematica and especially Simulink which are used very successfuly over a range of applications. However, the failure of Expert Systems, Fuzzy logic, and Japan's Fifth Generation computer project of the 80's to take-off demonstrate the difficulty in doing this.
Labview is a very successful none programatic programming environment.
What an interesting problem.
I would have to ultimately agree with you, and disagree with your colleague.
The philosophy and approach of Domain Driven Development/Design exists exactly for your purposes, in that it puts paramount importance on the specific knowledge of the experienced domain experts, and on communicating that knowledge to talented software developers.
See, in your issue, there are two distinct things. The domain, and the software. The domain should be understood and specified first and foremost without software development in mind.
And then the transformation to software happens between the communication between domain experts and programmers.
I think trying to build "programming" tools for domain experts is a waste of time.
In Domain Driven Development your domain experts will continue to be important, and you'll end up with better software.
In your colleague's approach you're trying to replace programmers with tool.... maybe in the future, like, start trek future, that will be possible, but today I don't think so.
I am currently struggling with a similar problem in trying to enable healthcare providers to write rules for workflows, which isn't easy because they aren't programmers. You're a programmer not because you went to programming school -- you're a programmer because you think like a programmer. Fortunately, most hospitals have some anesthesiologist or biomedical engineer who thinks like a programmer and can manage to program. The key is to give the non-programmers-who-think-like-programmers a language that they can learn and master.
In my case, I want doctors to be able to formulate simple rules, such as: "If a patient's temperature gets too low, send their doctor a text message". Of course it's more complicated than that because the definition of "too low" depends on the age of the patient, a patient may have many doctors, and so on, but a smart doctor will be able to figure out those rules. The real issue is that the temperature sensor will often fall off the patient and read ambient temperature, meaning that the rule is useless unless you can figure out how to determine that the thermometer is actually reading the patient's temperature.
The big problem I have is that, while it's relatively easy to create a DSL so that doctors can express IF [temperature] [less-than] [lookup-table [age]] THEN [send-text-message], it's much harder to create one that can express all the different heuristics you might need to try before coming up with the right way to make sure the reading is valid.
In your case, you may want to consider how VB became popular: It has a form drawing tool that anybody can easily use to draw forms and set properties on form items. Since not everything can be specified by form properties and data binding, there's a code-behind mode that lets you do complex logic. But to make the tool accessible to beginning programmers, the language is BASIC, so users didn't have to learn about pointers, memory allocation, or data structures.
While you probably wouldn't want to give your users VB, you might consider a hybrid approach. You would have one "language" (it could be graphical, like VB's form designer or Labview) where inexperienced users can easily do the simple stuff, and another language to enable expert users to do the complicated stuff.
I had this as a comment previously but I figured it deserved more merit.
There are definitely a number of successful 'non-programmatic' tools around, off hand I can think of Labview, VPL and graph based (edit: I just noticed this link has more far more than just shaders on it) shaders which are prevalent in 3D applications.
Having said that, I don't know of any which are suited to web based dev (which appears to be your case).
I dout very much the investment on developing such tools would be worth it (unless maybe you could move to sell it as a product as well).
I agree with you - non-technical people will not be able to program anything non-trivial.
Some products try to create what's basically a really simple programming language. The problem is that programming is an aptitude as well as a skill. It takes a certain kind of mindset to think in the sort of logic used by computers, which just can't be abstracted away by any programming language (at least not without without making assumptions that it can't safely make).
I've seen this in action with business people trying to construct workflows in MS Dynamics CRM. Even though the product was clearly intended to allow them to do it without a programmer they just couldn't figure out how to make a loop or an if-else condition work, no matter how "friendly" the UI tried to make it. I watched in amazement as they struggled with something that seemed completely self-obvious to me. After a full day (!) of this they managed to produce a couple of very basic workflows that worked in some cases, but didn't handle edge cases like missing values or invalid data. It was basically a complete waste of time.
Granted, Dynamics CRM isn't exactly the epitome of user-friendliness, but I saw enough to convince me that this is, indeed, a fool's errand.
Now, if your users are not programmers, but still technical people they might be able to learn programming, but that's another story - they've really become "new programmers" rather than "non-programmers" then.
This is a pretty philosophical topic and difficult to answer for every case, but in general...
Is non-programmatic development a fools errand?
Outside of a very narrow scope, yes. Major software vendors have invested billions over the years in creating various packages to try to let non-technical users create & define workflows and processes with limited success. Your best bet is to take advantage of what has been done in that space rather than trying to re-invent it.
Edit:
Sharepoint, InfoPath, some SAP stuff are the examples I'm talking about. As I said above, "a very narrow scope". It's possible to let non-programmers create workflows, complex forms, some domain processes, but that's it. Anything more general-purpose is simply trying to make non-programmers into programmers by giving them very crude tools.
Non programatic software development IS feasable, as long as you are realistic about what non-developers can reasonaby achieve - its all about a compromise between capability and ease of use.
The key is to break the requirements down cleanly into things that the domain experts need to be able to do, and spend time implementing those features in a foolproof way - The classic mistake is to try to let the system to do too much.
For example suppose you want domain experts to be able to create a form with a masked text input:
Most developers will look at that requirement and create a fancy control which accepts some sort of regular expression and lets the domain expert do anything.
This is the classic developer way of looking at things, however it's likely that your domain expert does not understand regular expressions and the developer has missed the point of the reqirement which was for the domain expert to be able to create this form.
A better solution might have been to create a control that can be confgiured to mask either Email addresses or telephone numbers.
Yes this control is far less capable than the first control, and yes the domain experts have to ask developers to extend it when they want to be able to mask to car registration numbers, however the domain experts are able to use it.
It seems that the problem is of organizational nature and cannot be solved by technical means alone.
The root is that content creators are completely non-technical, yet have to perform inherently technical tasks of designing forms and writing Prolog rules. Various designers and DSLs can alleviate their problems, but never solve them.
Either reorganize system and processes so knowledge carriers actually enter knowledge - nothing else; or train content creators to perform necessary development with existing tools or may be DSLs.
Non-programmatic development can save from low-level chores, but striving to set up system once and let users indefinitely and unrestrictedly expand it is certainly a fools errands.
Computer games companies operate like this all the time, so far as I can tell: a few programmers and a lot of content creators who need to be able to control logic as well (like level designers).
It's also probably a healthy discipline to be able to separate your code from the data and rules driving it if you can.
I'm therefore with your colleague, but of course the specifics may not make this general solution appropriate!

When can you trust yourself to implement cryptography based solutions?

I've read quite a few times how I shouldn't use cryptography if I'm not an expert. Basically both Jeff and Eric tell you the same:
Cryptography is difficult, better buy the security solution from experts than doing it yourself.
I completely agree, for a start it's incredibly difficult to perceive all possible paths an scenario might take, all the possible attacks against it and against your solution... but then When should we use it?
I will face in a few months with the task of providing a security solution to a preexisting solution we have. That is, we exchange data between servers, second phase of the project is providing good security to it. Buying a third party solution will eat up the budget anyway so ... When is it good to use cryptography for a security solution? Even if you are not a TOP expert.
Edit: To clarify due to some comments.
The project is based on data transport across network locations, the current implementation allows for a security layer to be placed before transport and we can make any changes in implementation we like (assuming reasonable changes, the architecture is well design so changes should have an acceptable impact). The question revolves around this phrase from Eric Lippert:
I don’t know nearly enough about cryptography to safely design or implement a crypto-based security system.
We're not talking about reinventing the wheel, I had in mind a certain schema when I designed the system that implied secure key exchange, encryption and decryption and some other "counter measures" (man in the middle, etc) using C# .NET and the included cryptography primitives, but I'm by no means an expert in the field so when I read that, I of course start doubting myself. Am I even capable of implementing a secure system? Would it always be parts of the system that will be insecure unless I subcontract that part?
I think this blog posting (not mine!) gives some good guidelines.
Other than that there are some things you should never do unless you're an expert. This is stuff like implementing your own crypto algorithm (or your own version of a published algorithm). It's just crazy to do that yourself! (When there's CAPI, JCE, OpenSSL, ....)
Beyond that though if you're 'inventing' anything it's almost certainly wrong. In the Coding Horror post you linked to - the main mistake to my mind is that he's doing it a very low level and you just don't need to. If you were encrypting things in Java (I'm not so familiar with .NET) you could use Jasypt which uses strong default algorithms and parameters and doesn't require you to know about ECB and CBC (though, arguably, you should anyway just because...).
There is going to be a prebuilt system for just about anything you're going to want to do with crypto. If you're storing keys then theres KeyCzar, in other cases theres Jasypt. The point is if you're doing anything 'unusual' with crypto - you shouldn't be; if you're doing something not 'unusual' then you don't need to do the crypto yourself. Don't invent a new way to store keys, generate keys from passwords, verify signatures etc - it's not necessary, it's complicated and you'll almost certainly make a mistake unless you're very very careful...
So... I don't think you necessarily need to be afraid of encrypting things but be aware that if you're specifying algorithms and parameters to those algorithms directly in your code it is probably not good. There are exceptions to any rule but as in the blog post I linked above - if you type AES into your code you're doing it wrong!
The key "take-away" from the Matasano blog post is right at the end (note that TLS is a more precise name for SSL):
THOMAS PTACEK
GPG for data at rest. TLS for data in
motion.
NATE LAWSON
You can also use Guttman's cryptlib,
which has a sane API. Or Google
Keyczar. They both have really simple
interfaces, and they try to make it
hard to do the wrong thing. What we
need are fewer libraries with higher
level interfaces. But we also need
more testing for those libraries.
The rule of thumb with cryptography isn't that you shouldn't use it if you're not an expert; rather, it's that you shouldn't re-invent the wheel unless you're an expert. In other words, use existing implementations / libraries / algorithms as much as possible. For example, don't write your own cryptographic authentication algorithm, or come up with yet another way to store keys.
As for when to use it: whenever you have data that needs to be protected from having others see it. Beyond that, it comes down to which algorithms / approaches are best: SSL vs. IPsec vs. symmetric vs. PKI, etc.
Also, a word of advice: key management is often the most challenging part of any comprehensive cryptographic solution.
You have things backwards: first you must specify your actual requirements in detail ("provide a security solution" is meaningless marketing drivel). Then you look for ways to satisfy those specific requirements; croptography will satisfy some of them.
Example of requirements that cryptography can satisfy:
Protect data sent over publich channels from spying
Protect data against tampering (or rather, detect manipulated data)
Allow servers and clients as well as users to prove their identity to each other
You need to go through the same process as for any other requirement. What is the problem being solved, what is the outcome the users are looking for, how is the solution proposed going to be supported going forward, what are the timescales involved. Sometimes there is an off the shelf solution that does the job, sometimes what you want needs to be developed as a custom solution, and sometimes you'll choose a custom solution as it will work out more cost effective than an off the shelf one.
The same is true with security requirements, but the added complexity is that to do any sort of custom solution requires additional expertise in the technical teams (development, support etc). There is also the issue that the solution may need to be not only secure but recognised as secure. This may be far easier to achieve with an off the shelf solution.
And RickNZ is absolutely right - don't forget key management. Consider this right at the outset as part of the decision making process.
The question I would start by asking, is what are you trying to achieve.
If you are trying to just secure the transmission of the data from server a to server b, then there are a number of mechanisms you could use, which would require little work, such as SSL.
However if you are trying to secure all of the data stored in the application that is a far more difficult, although if it is a requirement, then I would suggest that any cryptography, regardless of how easy to break, is better than none.
As someone who has been asked to do similar things, you face a daunting number of questions in implementing your system. There are major difference between securing a system and implementing cryptography systems.
Implementing a cryptography system is very difficult and experts routinely get it wrong, both in theory and practice. A famous theoretical failure was the knapsack cryptosystem which has been largely abandoned due to the Lenstra–Lenstra–Lovász lattice basis reduction algorithm. On the other side, we saw in the last year how an incorrect seed in Debian's random number generator opened up any key generated by the OS. You want to use a prepackaged cryptosystem, not because its an "experts-only" field, but because you want a community tested and supported system. Almost every cryptographic algorithm I know of has bounds that assume certain tasks to be hard, and if those tasks turn out to be computable (as in the LLL algorithm) the whole system becomes useless over night.
But, I believe, the real heart of the question is how to use things in order to make a secure system. While there are many libraries out there to generate keys, cipher the text, and so on, there are very few systems that implement the entire package. But as always security boils down to two concepts: worth of protection and circle of trust.
If you are guarding the Hope diamond, you spend a lot of money designing a system to protect it, employ a constant force to watch it, and hire crackers to continually try to break in. If you are just discouraging bored teenagers from reading your email, you hack something up in an hour and you don't use that address for secret company documents.
Additionally managing the circle of trust is just as difficult of a task. If your circle includes tech savvy, like-minded friends, you make a system and give them a large amount of trust with the system. If it includes many levels of trust, such as users, admins, and so on, you have a tiered system. Since you have to manage more and more interactions with a larger circle, the bugs in the larger system become more weaknesses to hack and thus you must be extremely careful in designing this system.
Now to answer your question. You hire a security expert the moment the item you're protecting is valuable enough and your circle of trust includes those you cannot trust. You don't design cryptography systems unless you do it for a living and have a community to break them, it is a full time academic discipline. If you want to hack for fun, remember that it is only for fun and don't let the value of what you are protecting get too high.
Pay for security (of which cryptography is a part but only a part) what it is worth but no more. So your first task is to decide what your security is worth, or or how much various states of security are worth. Then invite whoever holds the budget to select which state to aim for and therefore how much to spend.
No absolutes here, it's all relative.
Why buy cryptography? It's one of the most developed area in open source software of great quality :) See for example TrueCrypt or OpenSSL
There is a good chance that whatever you need cryptography for there is already a good quality, reputable open source project for it! (And if you can see the source you can see what they did; I once saw an article about a commercial software supposed to "encrypt" a file that simply xorred every byte with a fixed value!)
And, also, why would you want to re-invent the wheel? It's unlikely that with no cryptography background you will do better or even come close to the current algorithms such as AES.
I think it totally depends on what you are trying to achieve.
Does the data need to be stored encrypted at either end or does it just need to be encrypted whilst in transit?
How are you transferring the data? FTP, HTTP etc?
Probably not a good idea to have security as a second phase as by that point presumably you've been moving data around insecurely for a period of time?

Resistance to performance testing for a big bang rewrite?

I've been working on a "big bang" rewrite for, literally, over two years. The management has consistently and relentlessly ignored and belittled my calls to allocate time / resources for performance measurement, capacity planning, and optimization before the app replaces their mega-millions money maker flagship web app.
Finally, they have agreed to do it (and we successfully prevented them from big-banging by bringing up a parallel beta server that is in production now and will be the target of the tests). I don't like that they waited until the end to prioritize this, but it's better late than never.
What suggestions does everyone have for dealing with situations like these in the future? What is the best way to educate managers / clients about the need for these kinds of tests.
I've shown them Microsoft's performance guide on CodePlex, complete with its stark warnings from seasoned professionals in the opening pages. I've also shown them the book "Release It!" and the guidance its author gives about "the 3 am call". That has finally convinced them reluctantly, but the truth is that this should have been prioritized into the development and partly measured during development prior to final complete system testing.
Many managers and old-school engineers who wrote ASP only, but never did .NET, are used to coding everything themselves and don't understand all the options for caching, tuning, and health monitoring in newer .NET apps.
Thanks
What you didn't realize (and many engineers don't) is that this was a "sales situation", not an engineering one. It doesn't matter if the customer is in-house or not, the process is largely the same.
Sales is all about finding out what kind of problems drive your customers and then showing how your product solves one or more of their problems. If they don't think they have a performance problem, then they don't -- it's that simple. Although you may be able to educate them to the point where they see things your way, "educational selling" is expensive in time and money, and many customers resent being told "something they already know." It sounds like you had to educate this group by beating them over the head with the book, but there may have been easier ways to accomplish your goal.
What would it have been? I don't know, but they do, so ask them. Ask what it was that ultimately pushed them to making the decision. It might have been a sudden realization that you were right, but more likely it was something more basic, like a growing fear of being humiliated in the boardroom or the marketplace. They are unlikely to say so directly, but if you really listen to their answers you may be able to read between the lines. In sales, doing a postmortem on a sales call (successful or not) is critical to understanding what motivates your customer and how you can tune your own skills in presenting ideas.
And, next time, you will know to ask open-ended questions about what your customer wants to achieve, and what his/her problems are now and in the long run. Will it always work? Of course not, but learning to deal with the social side of engineering issues is a valuable skill to acquire.
Get them to agree on solid numbers for what they expect the system to be able to support (number of concurrent users/tasks/etc), then it becomes an obvious part of the development work to make certain the system can meet the requirements.
Don't discuss this as an open-ended performance tuning and benchmarking process, as that will make older managers concerned that you're on a fishing expedition or gold-plating the system.
Instead, discuss it as a certification exercise. Identify your current traffic levels, add in a safety margin, and explain that your testing is intended to certify that the system will stand up to real life.
You can still do the performance hotspot work; you just need to give the pointy haired bosses comfrt that all of your work is going to tangible business objectives.
There are all sorts of ways of convincing people - the examples you mention are "invoke higher authority". Most managers, however, would not necessarily be persuaded by technical guidance.
For situations like this, I've used a risk-based approach. For each project, I keep a risk log, identifying the biggest risks to the project, their likelihood, impact, and mitigation options. Often, you can quantify those items - and that allows managers to make a good decision.
At the very start of the re-write, your risk log might have had the following entry:
Risk: System performance fails to meet user expectations
Likelihood: unknown
Impact: end users abandon the website due to excessive load times. Project fails.
Cost of impact: $$$whatever your project cost.
Mitigation: fortnightly performance tests.
Mitigation cost: $$$whatever you think it would cost in time and money
Recommendation: run performance test to quantify the risk.
Most managers would be very uncomfortable with a risk whose likelihood is unknown, but whose cost is the failure of the project. On the other hand, you're not asking for a huge commitment - just enough to quantify the risk.
I like to review the risk log regularly with the project stakeholders - at least monthly. I always start with the "high impact/high likelihood" risks, but then move to the "high impact/unknown likelihood" risks. It's also a good idea to distribute meeting notes, recording the stakeholder decisions on each risk. Again, a manager who sees their name attached to a decision to ignore a high-impact risk, in a written record, will think carefully about the decision.
Once you can quantify the risk - by running some performance tests - you can make further risk-based decisions, based on the cost and likelihood of performance problems. This is also a good way to manage the other classic non-functional issues like security, accessibility and scalability.
By quantifying the issue, you turn it into a business decision, not an engineering decision.
Take careful notes about this development project, including what performance problems crop up after deployment. People will bemoan the problems, and you can tactfully suggest that they prioritize that sort of problem higher earlier. Some people will only accept direct first-person evidence.

Why is security through obscurity a bad idea? [closed]

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I recently came across a system where all of the DB connections were managed by routines obscured in various ways, including base 64 encoding, md5sums and various other techniques.
Why is security through obscurity a bad idea?
Security through obscurity would be burying your money under a tree. The only thing that makes it safe is no one knows it's there. Real security is putting it behind a lock or combination, say in a safe. You can put the safe on the street corner because what makes it secure is that no one can get inside it but you.
As mentioned by #ThomasPadron-McCarty below in a comment below:
If someone discovers the password, you can just change the password, which is easy. If someone finds the location, you need to dig up the money and move it somewhere else, which is much more work. And if you use security by obscurity in a program, you would have to rewrite the program.
Security through obscurity can be said to be bad because it often implies that the obscurity is being used as the principal means of security. Obscurity is fine until it is discovered, but once someone has worked out your particular obscurity, then your system is vulnerable again. Given the persistence of attackers, this equates to no security at all.
Obscurity should never be used as an alternative to proper security techniques.
Obscurity as a means of hiding your source code to prevent copying is another subject. I'm rather split on that topic; I can understand why you might wish to do that, personally I've never been in a situation where it would be wanted.
Security through obscurity is an interesting topic. It is (rightly) maligned as a substitute for effective security. A typical principle in cryptography is that a message is unknown but the contents are not. Algorithms for encyrption are typically widely published, analyzed by mathematicians and, after a time, some confidence is built up in their effectivness but there is never a guarantee that they're effective.
Some people hide their cryptographic algorithms but this is considered a dangerous practice because then such algorithms haven't gone through the same scrutiny. Only organisations like the NSA, which has a significant budget and staff of mathematicians, can get away with this kind of approach.
One of the more interesting developments in recent years has been the risk of steganography, which is the practice is hiding message in images, sound files or some other medium. The biggest problem in steganalysis is identifying whether or not a message is there or not, making this security through obscurity.
Last year I came across a story that Researchers Calculate Capacity of a Steganographic Channel but the really interesting thing about this is:
Studying a stego-channel in this way
leads to some counter-intuitive
results: for example, in certain
circumstances, doubling the number of
algorithms looking for hidden data can
increase the capacity of the
steganographic channel.
In other words, the more algorithms you use to identify messages the less effective it becomes, which goes against the normal criticism of security through obscurity.
Interesting stuff.
The main reason it is a bad idea is that it does not FIX the underlying problems, just attempts to hide them. Sooner or later, the problems will be discovered.
Also, extra encryption will incur additional overhead.
Finally excessive obscurity (like using checksums) makes maintenance a nightmare.
Better security alternatives is to eliminate potential weaknesses in your code such as enforced inputs to prevent injection attacks.
One factor the ability to recover from a security breach. If someone discovers your password, just reset it. But if someone uncovers your obscure scheme, you're hosed.
Using obscurity as all these people agree is not security, its buying yourself time. That said having a decent security system implemented then adding an extra layer of obscurity is still useful. Lets say tomorrow someone finds an unbeatable crack/hole in the ssh service that can't be patched immediately.
As a rule I've implemented in house... all public facing servers expose only the ports needed ( http/https ) and nothing more. One public facing server then will have ssh exposed to the internet at some obscure high numbered port and a port scanning trigger setup to block any IP's that try to find it.
Obscurity has its place in the world of security, but not as the first and last line of defense. In the example above, I don't get any script/bot attacks on ssh because they don't want to spend the time searching for a non-standard ssh service port and if they do, their unlikely to find it before another layer of security steps in and cuts them off.
All of the forms of security available are actually forms of security through obscurity. Each method increases in complexity and provides better security but they all rely on some algorithm and one or more keys to restore the encrypted data. "Security through obscurity" as most call it is when someone chooses one of the simplest and easiest to crack algorithms.
Algorithms such as character shifting are easy to implement and easy to crack, that's why they are a bad idea. It's probably better than nothing, but it will, at most, only stop a casual glance at the data from being easily read.
There are excellent resources on the Internet you can use to educate yourself about all of the available encryption methods and their strengths and weaknesses.
Security is about letting people in or keeping them out depending on what they know, who they are, or what they have. Currently, biometrics aren't good at finding who you are, and there's always going to be problems with it (fingerprint readers for somebody who's been in a bad accident, forged fingerprints, etc.). So, actually, much of security is about obfuscating something.
Good security is about keeping the stuff you have to keep secret to a minimum. If you've got a properly encrypted AES channel, you can let the bad guys see everything about it except the password, and you're safe. This means you have a much smaller area open to attack, and can concentrate on securing the passwords. (Not that that's trivial.)
In order to do that, you have to have confidence in everything but the password. This normally means using industry-standard crypto that numerous experts have looked at. Anybody can create a cipher they can't break, but not everybody can make a cipher Bruce Schneier can't break. Since there's a thorough lack of theoretical foundations for cipher security, the security of a cipher is determined by having a lot of very smart and knowledgeable people try to come up with attacks, even if they're not practical (attacks on ciphers always get better, never worse). This means the crypto algorithm needs to be widely known. I have very strong confidence in the Advanced Encryption Standard, and almost none in a proprietary algorithm Joe wrote and obfuscated.
However, there's been problems with implementations of crypto algorithms. It's easy to inadvertantly leave holes whereby the key can be found, or other mischief done. It happened with an alternate signature field for PGP, and weaknesses with SSL implemented on Debian Linux. It's even happened to OpenBSD, which is probably the most secure operating system readily available (I think it's up to two exploits in ten years). Therefore, these should be done by a reputable company, and I'd feel better if the implementations were open source. (Closed source won't stop a determined attacker, but it'll make it harder for random good guys to find holes to be closed.)
Therefore, if I wanted security, I'd try to have my system as reliable as possible, which means as open as possible except for the password.
Layering security by obscurity on top of an already secure system might help some, but if the system's secure it won't be necessary, and if it's insecure the best thing is to make it secure. Think of obscurity like the less reputable forms of "alternative medicine" - it is very unlikely to help much, and while it's unlikely to hurt much by itself it may make the patient less likely to see a competent doctor or computer security specialist, whichever.
Lastly, I'd like to make a completely unsolicited and disinterested plug for Bruce Schneier's blog, as nothing more than an interested reader. I've learned a lot about security from it.
One of the best ways of evaluating, testing or improving a security product is to have it banged on by a large, clever peer group.
Products that rely for their security on being a "black box" can't have the benefit of this kind of test. Of course, being a "black box" always invites the suspicion (often justified) that they wouldn't stand up to that kind of scrutiny anyway.
I argued in one case that password protection is really security through obscurity. The only security I can think of that wouldn't be STO is some sort of biometric security.
Besides that bit of semantics and nit picking, STO (Security through obscurity) is obviously bad in any case where you need real security. However, there might be cases where it doesn't matter. I'll often XOR pad a text file i don't want anyone reading. But I don't really care if they do, i'd just prefer that it not be read. In that case, it doesn't matter, and an XOR pad is a perfect example of an easy to find out STO.
It is almost never a good idea. It is the same to say, is it a good idea to drive without seatbelt? Of course you can find some cases where it fits, but the anwser due to experience seems obvious.
Weak encryption will only deter the least motivated hackers, so it isn't valueless, it just isn't very valuable, especially when strong encryption, like AES, is available.
Security through obscurity is based on the assumption that you are smart and your users are stupid. If that assumption is based on arrogance, and not empirical data, then your users- and hackers-- will determine how to invoke the hidden method, bring up the unlinked page, decompile and extract the plain text password from the .dll, etc.
That said, providing comprehensive meta-data to users is not a good idea, and obscuring is perfectly valid technique as long as you back it up with encryption, authorization, authentication and all those other principles of security.
If the OS is Windows, look at using the Data Protection API (DPAPI). It is not security by obscurity, and is a good way to store login credentials for an unattended process. As pretty much everyone is saying here, security through obscurity doesn't give you much protection.
http://msdn.microsoft.com/en-us/library/ms995355.aspx
http://msdn.microsoft.com/en-us/library/ms998280.aspx
The one point I have to add which hasn't been touched on yet is the incredible ability of the internet to smash security through obscurity.
As has been shown time and time again, if your only defense is that "nobody knows the back door/bug/exploit is there", then all it takes is for one person to stumble across it and, within minutes, hundreds of people will know. The next day, pretty much everyone who wants to know, will. Ouch.

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