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In our wanderings we’ve noticed that when we pull our heads out of the bubble, not everyone necessarily understands what cloud is or where it’s going. Heck, many smart IT people are still framing it within the context of what they currently do. It’s only natural, especially when they get crappy advice from clueless consultants, but it certainly can lead you down some ugly paths. This week Mike, Adrian and Rich are also joined by Dave Lewis (who accidentally sat down next to Rich at a conference) to talk about how people see cloud, the gaps, and how to navigate the waters. Watch or listen: Share:

Rich here. Okay, have I mentioned how impatient I’m getting about updating our site? Alas, there is only so fast you can push a good design and implementation. The foundation is all set and we hope to start transferring everything into our new AWS architecture within the next month. In the meantime I just pushed some new domain outlins for the Cloud Security Alliance Guidance into the GitHub repository for public feedback. I’m also starting to tie together the labs for our Black Hat USA 2016 | Advanced Cloud Security and Applied SecDevOps training. I have this weird thing where I like labs to build up into a full stack that resembles something you might actually deploy. It works well, but takes a lot more time to piece together. If you want to subscribe directly to the Friday Summary only list, just click here. Top Posts for the Week This continues the huge legal problems due to pressures from U.S. law enforcement. It’s aligned with the Microsoft case in Ireland and the Apple vs. FBI issues here. Basically, it’s going to be very hard for U.S. tech companies to compete internationally if they can’t assure customers they meet local privacy and security laws: Microsoft sues US government over ‘unconstitutional’ cloud data searches This topic comes up a lot. One interesting thing I hadn’t seen before is the ability to inject activity into your AWS account so you can run a response test (slide 13). Let me know if this is possible on other cloud providers: Security Incident Response and Forensics on AWS Google Compute Platform racks up some more certifications. Normally I don’t cover each of these, but from time to time it’s worth highlighting that the major providers are very aggressive on their audits and certifications: Now playing: New ISO security and privacy certifications for Google Cloud Platform There are two papers linked on this Azure post on security and incident response. The IR one should be of particular interested to security pros: Microsoft Incident Response and shared responsibility for cloud computing An interview and transcript from some top-notch DevOps security pros: Rugged DevOps: Making Invisible Things Visible Zero trust is a concept that’s really starting to gain some ground. I know one client who literally doesn’t trust their own network and users need to VPN in even from the office, and all environments are compartmentalized. This is actually easier to do in the cloud vs. a traditional datacenter, especially if you use account segregation: Zero Trust Is a Key to DevOps Security. While it doesn’t look like anyone exploited this vulnerability, still not good, and Office365 is one of the most highly tested platforms out there. Office 365 Vulnerability Exposed Any Federated Account I keep bouncing around testing the different platforms. So far I like Ansible better for deployment pipelines, but Chef or Puppet for managing live assets. However, I don’t run much that isn’t immutable, so I thus don’t have a lot of experience running them at scale in production. If you have any opinions, please email me: Ansible vs Chef . Nothing interesting…. Tool of the Week Two weeks ago I picked the Gauntlt security testing tool as the Tool of the Week. This week I’ll add to the collection with BDD-Security by ContinuumSecurity (it’s also available on GitHub). BDD stands for “Behavior Driven Development”. It’s a programming concept outside of security that’s also used for application testing in general. Conceptually, you define a test as “given A when X then Y”. In security terms this could be, “given a user logs in, and it fails four times, then block the user”. BDD-Security supports these kinds of tests and includes both some internal assessment features as well as the ability to integrate external tools, including Nessus, similar to Gauntlt. Here’s what it would look like directly from an Adobe blog post on the topic: Scenario: Lock the user account out after 4 incorrect authentication attempts Meta: @id auth_lockout Given the default username from: users.table And an incorrect password And the user logs in from a fresh login page 4 times When the default password is used from: users.table And the user logs in from a fresh login page Then the user is not logged in These tools are designed to automate security testing into the development pipeline but have the added advantage of speaking to developers on their own terms. We aren’t hitting applications with some black box scanner from the outside that only security understands, we are integrating our tools in a familiar, accepted way, using a common language. Securosis Blog Posts this Week Incite 4/27/2016–Tap the B.R.A.K.E.S.. Building a Vendor IT Risk Management Program: Ongoing Monitoring and Communication. Building a Vendor IT Risk Management Program: Evaluating Vendor Risk. Other Securosis News and Quotes Quiet week Training and Events I’m keynoting a free seminar for IBM at the Georgia Aquarium on May 18th. I’ve been wanting to go there for years, so I scheduled a late flight out if you want to stalk me as I look at fish for the next few hours. I’m presenting a session and running a half-day program at Interop next week. Both are on cloud security. I’m also presenting at the Rocky Mountain Information Security Conference in Denver on May 11/12. Although I live in Phoenix these days Boulder is still my home town and I’m psyched anytime I get back there. Message me privately if you get in early and want to meet up. We are running two classes at Black Hat USA. Early bird pricing ends in a month, just a warning: Black Hat USA 2016 | Cloud Security Hands-On (CCSK-Plus) Black Hat USA 2016 | Advanced Cloud Security and Applied SecDevOps Share:

I mentioned back in January that XX1 has gotten her driver’s permit and was in command of a two ton weapon on a regular basis. Driving with her has been, uh, interesting. I try to give her an opportunity to drive where possible, like when I have to get her to school in the morning. She can navigate the couple of miles through traffic on the way to her school. And she drives to/from her tutor as well, but that’s still largely local travel. Though I do have to say, I don’t feel like I need to run as frequently because the 15-20 minutes in the car with her gets my heart racing for the entire trip. Obviously having been driving for over 30 years, I see things as they develop in front of me. She doesn’t. So I have to squelch the urge to say, “Watch that dude over there, he’s about to change lanes.” Or “That’s a red light and that means stop, right?” Or “Hit the f***ing brakes before you hit that car, building, child, etc.” She only leveled a garbage bin once. Which caused more damage to her ego and confidence than it did to the car or the bin. So overall, it’s going well. But I’m not taking chances, and I want her to really understand how to drive. So I signed her up for the B.R.A.K.E.S. teen defensive driver training. Due to some scheduling complexity taking the class in New Jersey worked better. So we flew up last weekend and we stayed with my Dad on the Jersey Shore. First, a little digression. When you have 3 kids with crazy schedules, you don’t get a lot of individual time with any of the kids. So it was great to spend the weekend with her and I definitely got a much greater appreciation for the person she is in this moment. As we were sitting on the plane, I glanced over and she seemed so big. So grown up. I got a little choked up as I had to acknowledge how quickly time is passing. I remember bringing her home from the hospital like it was yesterday. Then we were at a family event on Saturday night with some cousins by marriage that she doesn’t know very well. To see her interact with these folks and hold a conversation and be funny and engaging and cute. I was overwhelmed with pride watching her bring light to the situation. But then it was back to business. First thing Sunday morning we went over the race track. They did the obligatory video to scare the crap out of the kids. The story of B.R.A.K.E.S. is a heartbreaking one. Doug Herbert, who is a professional drag racer, started the program after losing his two sons in a teen driving accident. So he travels around the country with a band of other professional drivers teaching teens how to handle the vehicle. The statistics are shocking. Upwards of 80% of teens will get into an accident in their first 3 years of driving. 5,000 teen driving fatalities each year. And these kids get very little training before they are put behind the wheel to figure it out. The drills for the kids are very cool. They practice accident avoidance and steering while panic breaking. They do a skid exercise to understand how to keep the car under control during a spin. They do slalom work to make sure they understand how far they can push the car and still maintain control. The parents even got to do some of the drills (which was very cool.) They also do a distracted driving drill, where the instructor messes with the kids to show them how dangerous it is to text and play with the radio when driving. They also have these very cool drunk goggles, which simulates your vision when under the influence. Hard to see how any of the kids would get behind the wheel drunk after trying to drive with those goggles on. I can’t speak highly enough about the program. I let XX1 drive back from the airport and she navigated downtown Atlanta, a high traffic situation on a 7 lane highway, and was able to avoid an accident when a knucklehead slowed down to 30 on the highway trying to switch lanes to make an exit. Her comfort behind the wheel was totally different and her skills were clearly advanced in just the four hours. If you have an opportunity to attend with your teen, don’t think about it. Just do it. Here is the schedule of upcoming trainings, and you should sign up for their mailing list. The training works. They have run 18,000 teens through the program and not one of them has had a fatal accident. That’s incredible. And important. Especially given my teen will be driving without me (or her Mom) in the car in 6 months. I want to tip the odds in my favor as much as I can. –Mike Security is changing. So is Securosis. Check out Rich’s post on how we are evolving our business. We’ve published this year’s Securosis Guide to the RSA Conference. It’s our take on the key themes of this year’s conference (which is really a proxy for the industry), as well as deep dives on cloud security, threat protection, and data security. And there is a ton of meme goodness… Check out the blog post or download the guide directly (PDF). The fine folks at the RSA Conference posted the talk Jennifer Minella and I did on mindfulness at the 2014 conference. You can check it out on YouTube. Take an hour. Your emails, alerts, and Twitter timeline will be there when you get back. Securosis Firestarter Have you checked out our video podcast? Rich, Adrian, and Mike get into a Google Hangout and… hang out. We talk a bit about security as well. We try to keep these to 15 minutes or less, and usually fail. Mar 16 – The Rugged vs. SecDevOps Smackdown Feb 17 – RSA Conference – The Good, Bad and Ugly Dec

As we mentioned last post, after you figure out what risk means to your organization, and determine the best way to quantify and rank your vendors in terms that concept of risk, you’ll need to revisit your risk assessment; because security in general, and each vendor’s environment specifically, is dynamic and constantly changing. We also need to address how to deal with vendor issues (breaches and otherwise) – both within your organization, and potentially to customers as well. Ongoing Monitoring When keeping tabs on your vendors you need to decide how often to update your assessments of their security posture. In a perfect world you’d like a continuous view of each vendor’s environment, to help you understand your risk at all times. Of course continuous monitoring costs. So part of defining a V(IT)RM program is figuring out the frequency of assessment. We believe vendors should not all be treated alike. The vendors in your critical risk tier (described in our last post) should be assessed as often as possible. Hopefully you’ll have a way (most likely through third-party services) of continually monitoring their Internet footprint, and alerting you when something changes adversely. We need to caveat that with a warning about real-time alerts. If you are not staffed to deal with real-time alerts, then getting them faster doesn’t help. In other words, if it takes you 3 days to work through your alert queue, getting an alert within an hour cannot reduce your risk much. Vendors in less risky tiers can be assessed less frequently. An annual self-assessment and a quarterly scan might be enough for them. Again, this depends on your ability to deal with issues and verify answers. If you aren’t going to look at the results, forcing a vendor to update their self-assessment quarterly is just mean, so be honest with yourself when determining the frequency for assessments. With assessment frequency determined by risk tier, what next? You’ll find adverse changes to the security posture of some vendors. The next step in the V(IT)RM program is to figure out how to deal with these issues. Taking Action You got an alert that there is an issue with a vendor, and you need to take action. But what actions can you take, considering the risk posed by the issue and the contractual agreement already in place? We cannot overstate the importance of defining acceptable actions contractually as part of your vendor onboarding process. A critical aspect of setting up and starting your program is ensuring your contracts with vendors support your desired actions when an issue arises. So what can you do? This list is pretty consistent with most other security processes: Alert: At minimum you’ll want a line of communication open with the vendor to tell them you found an issue. This is no different than an escalation during an incident response. You’ll need to assemble the information you found, and package it up for the vendor to give them as much information as practical. But you need to balance how much time you’re willing to spend helping the vendor against everything else on your to do list. Quarantine: As an interim measure, until you can figure out what happened and your best course of action, you could quarantine the vendor. That could mean a lot of things. You might segment their traffic from the rest of your network. Or scrutinize each transaction coming from them. Or analyze all egress traffic to ensure no intellectual property is leaking. The point is that you’ll need time to figure out the best course of action, and putting the vendor in a proverbial penalty box can buy you that time. This is also contingent on being able to put a boundary around a specific vendor or service provider, which may not be possible, depending on what services they provide. Cut off: There is also the kill switch, which removes vendor access from your systems and likely ends the business relationship. This is a draconian action, but sometimes a vendor presents such risk, and/or doesn’t make the changes you require, so you may not have a choice. As mentioned above, you’ll need to make sure your contract supports this action. Unless you enjoy protracted litigation. The latter two options impact the flow of business between your organization and the vendor, so you’ll need a process in place internally to determine if and when you quarantine and/or cut off a vendor. This escalation and action plan needs to be defined ahead of time. The rules of engagement, and the criteria to suspend or end a business relationship due to IT risk, need to be established ahead of time. Defined escalations ensure the internal stakeholders are in the loop as you consider flipping the kill switch. A good rule of thumb is that you don’t want to surprise anyone when a vendor goes into quarantine or is cut off from your systems. If the business decision is made to keep the vendor active in your systems (a decision made well above your pay grade), at least you’ll have documentation that the risk was accepted by the business owner. Communicating Issues Once the action plan is defined, documented, and agreed upon, you’ll want to build a communication plan. That includes defining when you’ll notify the vendor and when you’ll communicate the issue internally. As part of the vendor onboarding process you need to define points of contact with the vendor. Do they have a security team you should interface with? Is it their business operations group? You need to know before you run into an issue. You’ll also want to make sure to have an internal discussion about how much you will support the vendor as they work through any issues you find. If the vendor has an immature security team and/or program, you can easily end up doing a lot of work for them. And it’s not like you have a bunch of time to do someone else’s work, right? Of course business owners may be unsympathetic to your plight when their key vendor is cut off. That’s

As we discussed in the first post in this series, whether it’s thanks to increasingly tighter business processes/operations with vendors andtrading partners, or to regulation (especially in finance) you can no longer ignore vendor risk management. So we delved into the structure and mapped out a few key aspects of a VRM program. Of course we are focused on the IT aspects of vendor management, which should be a significant component of a broader risk management approach for your environment. But that begs the question of how you can actually evaluate the risks of a vendor. What should you be worried about, and how can you gather enough information to make an objective judgement of the risk posed by every vendor? So that’s what we’ll explore in this post. Risk in the Eye of the Beholder The first aspect of evaluating vendor risk is actually defining what that risk means to your organization. Yes, that seems self-evident, but you’d be surprised how many organizations don’t document or get agreement on what presents vendor risk, and then wonder why their risk management programs never get anywhere. Sigh. All the same, as mentioned above, vendor (IT) risk is a component of a larger enterprise risk management program. So first establish the risks of working with vendors. Those risks can be broken up into a variety of buckets, including: Financial: This is about the viability of your vendors. Obviously this isn’t something you can control from an IT perspective, but if a key vendor goes belly up, that’s a bad day for your organization. So this needs to be factored in at the enterprise level, as well as considered from an IT perspective – especially as cloud services and SaaS proliferate. If your Database as a Service vendor (or any key service provider) goes away, for whatever reason, that presents risk to your organization. Operational: You contract with vendors to do something for your organization. What is the risk if they cannot meet those commitments? Or if they violate service level agreements? Again it is enterprise-level risk of the organization, but it also peeks down into the IT world. Do you pack up shop and go somewhere else if your vendor’s service is down for a day? Are your applications and/or infrastructure portable enough to even do that? Security: As security professionals this is our happy place. Or unhappy place, depending on how you feel about the challenges of securing much of anything nowadays. This gets to the risk of a vendor being hacked and losing your key data, impacting availability of your services, and/or allowing an adversary to jump access your networks and systems. Within those buckets, there are probably a hundred different aspects that present risk to your organization. After defining those buckets of risk, you need to dig into the next level and figure out not just what presents risk, but also how to evaluate and quantify that risk. What data do you need to evaluate the financial viability of a vendor? How can you assess the operational competency of vendors? And finally, what can you do to stay on top of the security risk presented by vendors? We aren’t going to tackle financial or operational risk categories, but we’ll dig into the IT security aspects below. Ask them The first hoop most vendors have to jump through is self-assessment. As a vendor to a number of larger organizations, we are very familiar with the huge Excel spreadsheet or web app built to assess our security controls. Most of the questions revolve around your organization’s policies, controls, response, and remediation capabilities. The path of least resistance for this self-assessment is usually a list of standard controls. Many organizations start with ISO 27002, COBIT, and PCI-DSS. Understand relevance is key here. For example, if a vendor is only providing your organization with nuts and bolts, their email doesn’t present a very significant risk. So you likely want a separate self-assessment tool for each risk category, as we’ll discuss below. It’s pretty easy to lie on a spreadsheet or web application. And vendors do exactly that. But you don’t have the resources to check everything, so there is a measure of trust, but verify that your need to apply here. Just remember that it’s resource-intensive to evaluate every answer, so focus on what’s important, based on the risk definitions above. External information Just a few years ago, if you wanted to assess the security risk of a vendor, you needed to either have an on-site visit or pay for a penetration test to really see what an attacker could do to partners. That required a lot of negotiation and coordination with the vendor, which meant it could only be used for your most critical vendors. And half the time they’d tell you to go pound sand, pointing to the extensive self-assessment you forced them to fill out. But now, with the introduction of external threat intelligence services, and techniques you can implement yourself, you can get a sense of what kind of security mess your vendors actually are. Here are a few types of relevant data sources: Botnets: Botnets are public by definition, because they use compromised devices to communicate with each other. So if a botnet is penetrated you can see who is connecting to it at the time, and get a pretty good idea of which organizations have compromised devices. That’s exactly how a number of services tell you that certain networks are compromised without ever looking at the networks in question. Spam: If you have a network that is blasting out a bunch of spam, that indicatives an issue. It’s straightforward to set up a number of dummy email accounts to gather spam, and see which networks are used to blast millions of messages a day. If a vendor owns one of those networks, that’s a disheartening indication of their security prowess. Stolen credentials: There are a bunch of forums where stolen credentials are traded, and if a specific vendor shows up with tons of their accounts and passwords for sale, that means their

Adrian here. Starting with the 2008 RSA conference, Rich and Chris Hoff presented each year on the then-current state of cloud services, and predicted where they felt cloud computing was going. This year Mike helped Rich conclude the series with some new predictions, but more importantly they went back to assess the accuracy of previous prognostications. My takeaway is that their predictions for what cloud services would do, and the value they would provide, were pretty well spot on. And in most cases, when a specific tool or product was identified as being critical, they totally missed the mark. Wildly. Trying to follow cloud services – Azure, AWS, and GCP, to name a few – is like running toward a rapidly-expanding explosion blast radius. Capabilities grow so fast in depth and breadth that you cannot keep pace. Part of our latest change to the Friday Summary is a weekly tools discussion to help you with the best of what we see. And ask IT folks or any development team: tools are a critical part of getting the job done. Adoption rates of Docker show how critical tools are to productivity. Keep in mind that we are not making predictions here – we are keenly aware that we don’t know what tools will be used a year from now, much less three. But we do know many old-school platforms don’t work in more agile situations. That’s why it’s essential to share some of the cool stuff we see, so you are aware of what’s available, and can be more productive. You can subscribe to only the Friday Summary. Top Posts for the Week Amazon Seeing ‘Momentous’ Change of Guard as Public Cloud ‘Booms,’ Says JP Morgan 6 roadblocks to cloud security, and how to move past them GitLab-Digital Ocean partnership to provide free hosting for continuous online code testing How Continuous Delivery Challenges Security Google Reimburses Cloud Clients After Massive Google Compute Engine Outage What does shared responsibility in the cloud mean? Microsoft takes an ‘apps for every platform’ approach with host of DevOps tools Internals of App Service Certificate Announcing the Preview of Storage Service Encryption for Data at Rest Tool of the Week This week’s tool is DynamoDB, a NoSQL database service native to Amazon AWS. A couple years ago when we were architecting our own services on Amazon, we began with comparing RDS and PostgreSQL, and even considered MySQL. After some initial prototyping work we realized that a relational – or quasi-relational, for some MySQL variants – platform really did not offer us any advantages but came some limitations, most notably around the use of JSON data elements and the need to store very small records very quickly. We settled on DynamoDB. Call it confirmation bias, but the more we used it the more we appreciated its capabilities, especially around security. While a full discussion of DynamoDB’s security capabilities – much less a full platform review – is way beyond the scope of this post, the following are some security features we found attractive: Query Filters: The ability to use filter expressions to simulate masking and label-based controls over what data is returned to the user. The Dynamo query can be consistent for all users, but filter return values after it is run. Filters can work by comparing elements returned from the query, but there is nothing stopping you from filtering on other values associated with the user running the query. And like with relational platforms, you can built your own functions to modify data or behavior depending upon the results. Fine-grained Authorization: Access polices can be used to restrict access to specific functions, and limit the impact of those functions to specific tables by user. As with query filters, you can limit results a specific user sees, or take into account things like geolocation to dynamically alter which data a user can access, using a set of access policies defined outside the application. IAM: The AWS platform offers a solid set of identity and access management capabilities, and group/role based authorization as you’d expect, which all integrates with Dynamo. But it also offers temporary credentials for delegation of roles. The also offer hooks to leverage Google and Facebook identities to cotnrol mobile access to the database. Again, we can choose to punt on some IAM responsibilities for speed of deployment, or we can choose to ratchet down access, depending on how the user authenticated. JSON Support: You can both store and query JSON documents in DynamoDB. Programmers reading this will understand why this is important, as it enables you to store everything from data to code snippets, in a semi-structured way. For security or DevOps folks, consider storing different versions of initialization and configuration scripts for different AMIs, or a list of defining characteristics (e.g., known email addresses, MAC addresses, IP addresses, mobile device IDs, corporate and personal accounts, etc.) for specific users. Logging: As with most NoSQL platforms, logging is integrated. You can set what to log conditionally, and even alert based on log conditions. We are just now prototyping log parsing with Lambda functions, streaming the results to S3 for cheap storage. This should be an easy way to enrich as well. DynamoDB has security feature parity with relational databases. As someone who has used relational platforms for the better part of 20 years, I can say that most of the features I want are available in one form or another on the major relational platforms, or can be simulated. The real difference is the ease and speed at which I can leverage these functions. Securosis Blog Posts this Week How iMessage distributes security to block “phantom devices” Summary: April 14, 2016 Other Securosis News and Quotes Rich quoted in Fortune Adrian quoted on WAF management Training and Events We are running two classes at Black Hat USA: Black Hat USA 2016 | Cloud Security Hands-On (CCSK-Plus) Black Hat USA 2016 | Advanced Cloud Security and Applied SecDevOps Share:

Last Friday I spent some time in a discussion with senior members of Apple’s engineering and security teams. I knew most of the technical content but they really clarified Apple’s security approach, much of which they have never explicitly stated, even on background. Most of that is fodder for my next post, but I wanted to focus on one particular technical feature I have never seen clearly documented before; which both highlights Apple’s approach to security, and shows that iMessage is more secure than I thought. It turns out you can’t add devices to an iCloud account without triggering an alert because that analysis happens on your device, and doesn’t rely (totally) on a push notification from the server. Apple put the security logic in each device, even though the system still needs a central authority. Basically, they designed the system to not trust them. iMessage is one of the more highly-rated secure messaging systems available to consumers, at least according to the Electronic Frontier Foundation. That doesn’t mean it’s perfect or without flaws, but it is an extremely secure system, especially when you consider that its security is basically invisible to end users (who just use it like any other unencrypted text messaging system) and in active use on something like a billion devices. I won’t dig into the deep details of iMessage (which you can read about in Apple’s iOS Security Guide), and I highly recommend you look at a recent research paper by Matthew Green and associates at Johns Hopkins University which exposed some design flaws. Here’s a simplified overview of how iMessage security works: Each device tied to your iCloud account generates its own public/private key pair, and sends the public key to an Apple directory server. The private key never leaves the device, and is protected by the device’s Data Protection encryption scheme (the one getting all the attention lately). When you send an iMessage, your device checks Apple’s directory server for the public keys of all the recipients (across all their devices) based on their Apple ID (iCloud user ID) and phone number. Your phone encrypts a copy of the message to each recipient device, using its public key. I currently have five or six devices tied to my iCloud account, which means if you send me a message, your phone actually creates five or six copies, each encrypted with the public key for one device. For you non-security readers, a public/private keypair means that if you encrypt something with the public key, it can only be decrypted with the private key (and vice-versa). I never share my private key, so I can make my public key… very public. Then people can encrypt things which only I can read using my public key, knowing nobody else has my private keys. Apple’s Push Notification Service (APN) then sends each message to its destination device. If you have multiple devices, you also encrypt and send copies to all your own devices, so each shows what you sent in the thread. This is a simplification but it means: Every message is encrypted from end to end. Messages are encrypted using keys tied to your devices, which cannot be removed (okay, there is probably a way, especially on Macs, but not easily). Messages are encrypted multiple times, for each destination device belonging to the recipients (and sender), so private keys are never shared between devices. There is actually a lot more going on, with multiple encryption and signing operations, but that’s the core. According to that Johns Hopkins paper there are exploitable weaknesses in the system (the known ones are patched), but nothing trivial, and Apple continues to harden things. Keep in mind that Apple focuses on protecting us from criminals rather than governments (despite current events). It’s just that at some point those two priorities always converge due to the nature of security. It turns out that one obvious weakness I have seen mentioned in some blog posts and presentations isn’t actually a weakness at all, thanks to a design decision. iMessage is a centralized system with a central directory server. If someone could compromise that server, they could add “phantom devices” to tap conversations (or completely reroute them to a new destination). To limit this Apple sends you a notification every time a device is added to your iCloud account. I always thought Apple’s server detected a new entry and then pushed out a notification, which would mean that if they were deeply compromised (okay, forced by a government) to alter their system, the notification could be faked, but that isn’t how it works. Your device checks its own registry of keys, and pops up an alert if it sees a new one tied to your account. According to the Johns Hopkins paper, they managed to block the push notifications on a local network which prevented checking the directory and creating the alert. That’s easy to fix, and I expect a fix in a future update (but I have no confirmation). Once in place that will make it impossible to place a ‘tap’ using a phantom device without at least someone in the conversation receiving an alert. The way the current system works, you also cannot add a phantom recipient because your own devices keep checking for new recipients on your account. Both those could change if Apple were, say, forced to change their fundamental architecture and code on both the server and device sides. This isn’t something criminals could do, and under current law (CALEA) the US government cannot force Apple to make this kind of change because it involves fundamental changes to the operation of the system. That is a design decision I like. Apple could have easily decided to push the notifications from the server, and used that as the root authority for both keys and registered devices, but instead they chose to have the devices themselves detect new devices based on new key registrations (which is why the alerts pop up on everything you own when you add or re-add a device).

Rich here. Mike, Adrian, and I are just back from a big planning session for what we are calling “Securosis 2.0”. Everything is lining up nicely, and now we mostly just need to get the website updated. We are fully gutting the current design and architecture, and moving everything into AWS. The prototyping is complete and next week I get to build out the deployment pipeline, because we are going with a completely immutable design. One nice twist is that the public side is all read-only, while we have a totally different infrastructure for the admin side. Both share a common database (MariaDB on RDS) and file store (S3). We are estimating about a 10X cost savings compared to our current high-security hosting. As we get closer I’ll start sharing more implementation tips based on our experience. This is quite different from our Trinity platform, which is completely bespoke, whereas in this case we have to work with an existing content management system and wrangle it into a cloud native deployment. If you want to subscribe directly to the Friday Summary only list, just click here. Top Posts for the Week This is a stunningly good presentation – filled with the kinds of specifics we rarely see (including naming tools). If you are serious about Rugged DevOps this is a must-read: Taking AppSec to 11 – BSides Austin 2016. Here’s another must-read from Ryan over at Slack. It describes a distributed notification and response system he built to dramatically improve response times by engaging all employees in security. It’s practical and highly effective: Distributed Security Alerting – Several People Are Coding I’m actually not convinced this next piece on Apple’s cloud creation is related directly to snooping. It’s pretty straightforward to block snooping when you host on a cloud provider and have Apple’s resources (perhaps not easy, but straightforward). To me this looks more like a mix of economics and wanting better control over a core technology. When you are as big as Apple (or heck, even little ol’ Dropbox) owning the infrastructure makes a lot of sense. Report: Apple developing at least 6 cloud infrastructure projects incl. servers to prevent snooping Amazon API Gateway Custom Authorization. We are looking hard at various auth options for Trinity, and I like the idea of building as little as possible. About two months ago I asked Adrian if we should drop dynamic masking from the cloud security training because I didn’t think anyone was doing it. Then I found out it’s built into Azure. Oops. Get started with SQL Database Dynamic Data Masking. And since I mentioned AWS and Azure, we might as well add a little Google Compute Platform into the mix. Here are some good best practices from Google themselves: Google shares data center security and design best practices. Tool of the Week Last week we set the stage with Jenkins and I hinted that this week we would start on some security-specific tools. It’s time to talk about Gauntlt, one of the best ways to integrate testing into your deployment pipeline. It is a must-have addition to any continuous deployment/delivery process. Gauntlt allows you to hook your security tools into your pipeline for automated testing. For example you can define a simple test to find all open ports using nmap, then match those ports to the approved list for that particular application component/server. If it fails the test you can fail the build and send the details back to your issue tracker for the relevant developer or admin to fix. Attacks (tests) are written in an easy-to-parse format. It’s an extremely powerful way to integrate automated security testing into the development and deployment process, using the same tools and hooks as development and operations themselves. Securosis Blog Posts this Week We were all out this week for our planning session, so no posts. Other Securosis News and Quotes David Mortman interviewed on container security: Containers and Security Q&A: Putting a Lid on Risk Training and Events We are running two classes at Black Hat USA: Black Hat USA 2016 | Cloud Security Hands-On (CCSK-Plus) Black Hat USA 2016 | Advanced Cloud Security and Applied SecDevOps (SOLD OUT! But we are considering opening more slots). Share:

Rich here. I started to write an apology for this week’s Summary, because I missed last week due to an unplanned stomach bug that hit at 4am Thursday, when I normally write these. It was nearly 5 days before I fully recovered. Then I realized I had fully drafted a Summary on March 11 – an abridged version due to my daughter waking up with a stomach infection. It turns out I left that one as a draft, and never even noticed… that’s what kids do to ya. So I’m including all my post-RSA conference links here, and adding some newer content as well. We’re building up a massive backlog of content at this point, so there’s no shortage of things to write about. And if you didn’t believe in the germ theory of infection, my home is conclusive proof. Someone emailed asking if we could cover more cloud providers than just AWS. We tend to focus on them because they are the biggest, and that’s where most of our work is, but we are actively trying to expand coverage. Email us at info@securosis.com if you have any interesting sites we should follow, or see any interesting presentations. There are a bunch of catch-up links here, but next week I plan to focus more on Microsoft and Google. If you want to subscribe directly to the Friday Summary only list, just click here. Top Posts for the Week My RSA presentation with Bill Shinn on how you can be more secure in the cloud. My Rugged DevOps at Scale presentation video from DevOps Connect at RSAC. Full Video Series Released: Rugged DevOps at RSA Conference 2016. Attack of the week: DROWN. This nasty one is affecting a lot of cloud deployments. Please review and patch. Rugged DevOps at RSAC 2016. A great summary by the author of Gauntlt. And not just because he mentions my session. Full disclosure: the idea of keeping all security documentation in GitHub comes from Bill Shinn of AWS. IAM best practice guides available now for Google Cloud. Google and Microsoft are starting to push hard to catch up with AWS on critical security capabilities. AWS launched a community repository for AWS Config Rules. Nice idea, and it gives you a good sense of various security and configuration requirements from different organizations. Snapchat shares security best practices for running on GCP. Migrating to AWS NAT Gateway. Expect to see more of these service endpoints. This one solves a problem we have seen customers hit: NAT instances aren’t always reliable. Although sometimes for security reasons you still want to proxy through instances rather than using this. Especially if you need to lock down Internet access beyond what you can do with security groups or ACLs. For 7 years Chris Hoff and I have co-presented an ongoing series at RSA on disruptive innovation and its impact on security. Chris couldn’t be there this year, and it seemed like time to bring things to a close. Mike Rothman filled in and you can see our review of all seven years, with implications, in our enormous deck. Innovating Security like the DevOps Unicorns. A nice interview with Shannon Lietz of Intuit. Probably one of the best DevOps security pros out there right now. Tool of the Week This is a new section highlighting a cloud, DevOps, or security tool we think you should take a look at. We still struggle to keep track of all the interesting tools that can help us, so if you have submissions please email them to info@securosis.com. This week I want to focus on a tool that is one of the cornerstones of DevOps in many organizations, but with which not all security professionals are familiar. We need this as a foundation so we can start talking about some cool security extensions next week. Thus, ladies and gentlemen, today we will talk about Jenkins. Jenkins is the most popular continuous integration tool right now. It’s Open Source with a very active community and a ton of support and plugins. For those of you without development experience, a CI server automates integrating application code changes and running tests. It can do a lot more than that, but continuously integrating changes (even from multiple teams’ contributors in massive projects) and making sure the code still works is a big deal. What makes Jenkins so special is that large community and massive plugin support. Instead of merely integrating updated code, it can detect when code is updated in a repository, pull it and integrate, automatically stand up a test environment, run thousands of tests, send alerts back on failures, or push code into further testing or production if it passes. The current version (and upcoming version 2.0) are automation servers that can handle complex workflows and pipelines for managing application updates. This automation offers tremendous security benefits. For example there is a full audit trail of all code changes. Better yet, you can integrate security testing into your automation pipeline, far more effectively than previous ways we’ve used security testing tools. You can flag changes to security-sensitive parts of code like encryption or authentication to require a security sign-off. All this using the same tool developers use anyway, and integrated into their processes. Jenkins isn’t just for code – you can use it for server configuration, and using a tool like Packer it can create gold images and perform automatic security scans. You can even run complex vulnerability assessments on cloud/virtual infrastructure using code templates like Vagrant, Cloudformation, or Terraform. Next week we’ll talk about one of the coolest security testing tools that integrates with Jenkins. Securosis Blog Posts this Week Incite 4/6/2016: Hindsight Incite 3/30/2016: Rational People Disagree Incite 3/23/2016: The Madness Resilient Cloud Network Architectures: Design Patterns Securing Hadoop: Security Recommendations for Hadoop [New Paper] Resilient Cloud Network Architectures: Fundamentals Shadow Devices: The Exponentially Expanding Attack Surface [New Series] Maximizing WAF Value Maximizing Value From Your WAF [New Series] Maximizing WAF Value: Deployment Maximizing WAF Value: Managing Your WAF Other Securosis News and Quotes At Macworld, I wrote How FBI vs. Apple could

As described in last post, deploying a WAF requires knowledge of both application security and your specific application(s). Management it requires an ongoing effort to keep a WAF current with emerging attacks and frequent application changes. Your organization likely adds new applications and changes network architectures at least a couple times a year. We see more and more organizations embracing continuous deployment for their applications. This means application functions and usage are constantly changing as well. So you need to adjust your defenses regularly to keep pace. Test & Tune The deployment process is about putting rules in place to protect applications. Managing the WAF involves monitoring it to figure out how well your rules are actually working, which requires spending a bunch of time examining logs to learn what is working and what’s not. Tuning policies for both protection and performance is not easy. As we have mentioned, you need someone who understands the rule ‘grammars’ and how web protocols work. That person must also understand the applications, the types of data customers should have access to within them, what constitutes bad behavior/application misuse, and the risks the web applications pose to the business. An application security professional needs to balance security, applications, and business skills, because the WAF policies they write and manage touch all three disciplines. The tuning process involves a lot of trial and error, figuring out which changes have unintended consequences like adding attack surface or breaking application functionality, and which are useful for protecting applications from emerging attacks. You need dual tuning efforts, one for positive rules which must be updated when new application functionality is introduced, and another for negative rules which protect applications against emerging attacks. By the time a WAF is deployed customers should be comfortable creating whitelists for applications, having gained a decent handle on application functionality and leveraging the automated WAF learning capabilities. It’s fairly easy to observe these policies in monitor-only mode, but there is still a bit of nail-biting as new capabilities are rolled out. You’ll be waiting for users to exercise a function before you know if things really work, after which reviewing positive rules gets considerably easier. Tuning and keeping negative security policies current still relies heavily on WAF vendor and third-party assistance. Most enterprises don’t have research groups studying emerging attack vectors every day. These knowledge gaps, regarding how attackers work and cutting-edge attack techniques, create challenges when writing specific blacklist policies. So you are will depend on your vendor for as long as you use WAF, which is why we stress finding a vendor who acts as a partner and building support into your contract. As difficult as WAF management is, there is hope on the horizon, as firms embrace continuous deployment and DevOps, and accept daily updates and reconfiguration. These security teams have no choice but to build & test WAF policies as part of their delivery processes. WAF policies must be generated in tandem with new application features, which requires security and development teams to work shoulder-to-shoulder, integrating security as part of release management. New application code goes through several layers of functional testing and WAF rules get tested as code goes into a production environment, but before exposure to the general public. This integrated release process is called Blue-Green deployment testing. In this model both current (Blue) and new (Green) application code are run, on their own servers, in parallel in a fully functional production environment, ensuring applications run as intended in their ‘real’ environment. The new code is gated at the perimeter firewall or routers, limiting access to in-house testers. This way in-house security and application teams can verify that both the application and WAF rules function effectively and efficiently. If either fails the Green deployment is rolled back and Blue continues on. If Green works it becomes the new public production copy, and Blue is retired. It’s early days for DevOps, but this approach enables daily WAF rule tuning, with immediate feedback on iterative changes. And more importantly there are no surprises when updated code goes into production behind the WAF. WAF management is an ongoing process – especially in light of the dynamic attack space blacklists addresses, false-positive alerts which require tuning your ruleset, and application changes driving your whitelist. Your WAF management process needs to continually learn and catalog user and application behaviors, collecting metrics as part of the process. Which metrics are meaningful, and which activities you need to monitor closely, differs between customers. The only consistency is that you cannot measure success without logs and performance metrics. Reviewing what has happened over time, and integrating that knowledge into your policies, is key to success. Machine Learning At this point we need to bring “machine learning” into the discussion. This topic generates confusion, so let’s first discuss what it means to us. In its simplest form, machine learning is looking at application usage metrics to predict bad behavior. These algorithms examine data including stateful user sessions, user behavior, application attack heuristics, function misuse, and high error rates. Additional data sources include geolocation, IP address, and known attacker device fingerprints (IoC). The goal is to detect subtler forms of application misuse, and catch attacks quickly and accurately. Think of it as a form of 0-day detection. You want to spot behavior you know is bad, even if you haven’t seen that kind of badness before. Machine learning is a useful technique. Detecting attacks as they occur is the ideal we strive for, and automation is critical because you cannot manually review all application activity to figure out what’s an attack. So you’ll need some level of automation, to both scale scarce resources and fit better into new continuous deployment models. But it is still early days for this technology – this class of protection has a ways to go for maturity and effectiveness. We see varied success: some types of attacks are spotted, but false positive rates can be high. And we are not fans of the term “machine learning” for this functionality, because it’s too generic. We’ve seen some vendors