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Adopting DevSecOps and integrating security into software is an obvious answer. Sooner or later, this method will conquer the software development field.

Agile development has a serious Appsec problem. Most Agile development teams suck at building secure software. But one of the reasons for this is that Appsec has a serious Agile problem. Most security experts don’t understand Agile development and haven’t come to terms with the way the way that Agile teams design and build software; with the way that Agile teams think and work; and especially with the speed at which Agile teams deliver software and make decisions. The CSSLP and Agile = Epic Fail You can see this problem in (ISC)2’s Certified Secure Software Lifecycle Professional (CSSLP), which is supposed to help bridge between security and software development. The Official Guide to the CSSLP is 572 pages long. Of this, only 2 pages are spent on Agile development: ½ page each on Scrum and XP, and a couple of pictures. Otherwise, ISC2 pretends that software development is done in big formal Waterfall steps (requirements, design, coding, testing, deployment) with lots of documents to review and clear hand-offs at each of these steps where somebody from Security can step in and insert a big formal review/test before the next step can start. Most developers don’t work this way anymore, if they ever did. Appsec’s Agile Challenges It’s not clear how and when security should engage with Agile teams that are following Lean, lightweight Agile methods. How can Security keep up with projects with such short-term planning horizons, plans and priorities that change for every 1- or 2-week sprint? What about teams following Kanban and Just in Time planning and “automagical” prioritization, and Continuous Deployment in Devops, pushing each change out to customers as soon as it is developed? Where does Security fit in Scrum, or a Scrum of Scrums? What meetings do security engineers need to attend, and what roles are they supposed to play in these meetings? How much input can they / should they have on decisions? Is Security a Chicken or a Pig? How can Security know when they need to do a security review, if requirements are all captured in 1-sentence User Stories which are “too short on purpose”? How do you get security activities and requirements included in the backlog? How can Security catch and correct design and implementation decisions before it is too late if they aren't in the same room as the development team, when developers are learning and deciding on the fly what work needs to be done and how it needs to be done? When do you schedule security reviews and tests if the design and the code are always changing? When the team is continuously experimenting and trying out new ideas, new programming models, new languages and frameworks and libraries and toolchains? How do you do threat modeling on a design that is never finished? And how can you assess the design of a system for security risks if “the design is the code” and “the code is the documentation” without having to go through all of the code by hand after it has already been written? Security and compliance requires a security review for every major software release. But what if there is never a “major release”, what if the development team is releasing small changes to production 20 or 50 or 500 or 5000 times a year? It Has Already Been Decided Appsec isn’t prepared for the rapid pace that Agile teams deliver working software, often from the start of a project. Or for the fierce autonomy and independence of self-managing Whole Teams in which developers are free to decide who will do the work and how it will get done. Or for the speed at which these decisions are made. This is a different way of thinking and working from top-down, plan-driven projects. Responsibility and accountability for decisions are pushed down to the team and from there to individuals. Lots of people making lots of small decisions, quickly and often – and changing or unmaking these decisions just as quickly and just as often. The ground is always shifting, as people continuously seek out and respond to feedback and new ideas and information, adjusting and backtracking and making course corrections. Constantly changing and tuning how they work through frequent retrospection. A culture and working approach where people are encouraged to fire first and then aim, to make mistakes and embrace failure, to fail early, fail fast and fail often, as long as they keep learning. The software – and the process that the team follows to design and build and test it – is never done, never stable and therefore “never secure”. Agile Appsec: Case Studies Microsoft has taken on the problem of how to do secure Agile development with its SDL-Agile process framework. Unfortunately, it only works for Microsoft: the SDL-Agile is expensive, heavyweight, and draws extensively on the scale and capabilities of Microsoft’s massive internal organization. Two “From the Trenches” case studies at this year’s OWASP Appsec USA conference in NYC showed how other organizations are taking on the same challenges. The first case study by Chris Eng and Ryan Boyle at Veracode, a software security as a service provider (couldn't find the link at OWASP) proves how difficult it can be for Appsec to keep up with Agile development teams, even in an organization that does Appsec for a living and has deep security engineering capabilities. Veracode’s internal Appsec engineering program has continued to learn and adapt as their development organization grew to more than 100 application developers working in a dozen Scrum teams. In the early pre-Agile days, their program relied on static analysis checking (essentially eating their own dog food as they used the same platform technology that the development team was building for customers), staged manual pen testing and ad hoc consultation from the security engineering team. As the development organization grew and adopted Scrum, Security had to find new ways to work closer with development without slowing the developers down or stretching their security engineering resources too thin. Security engineers got involved in Sprint planning meetings to discover risks, identify which stories needed security reviews, and do some threat modeling. But they found that planning meetings were not the best place for technical security reviews – the security engineers had already missed a lot of design and implementation decisions that developers had already made, which forced the teams to back track or add work after the Sprint had already started, making them miss their commitments. Now security engineers work earlier with the Product Owner to look for risks and to proactively review the team’s backlog and identify candidate stories that Security will need to review and sign-off on or help the team with. In the second case study, Yair Rovek explained how at LivePerson, 200+ developers in more than 20 Scrum teams build secure software using a common set of technologies, tools and practices. Security engineering works with a central architecture team to build security into the technology platform that all of the development teams share, including custom-built developer-friendly wrappers around ESAPI and other security libraries. Security reviews and other controls are added at different points in the development cycle: Release planning (identify risks, high-level design, compliance issues), Sprint planning, coding, testing, release. LivePerson uses static analysis tools with custom rules to check that architecture conventions are followed and to alert when a developer integrates new Open Source code so that this code can be reviewed for vulnerabilities. They schedule pen tests for every major release of their software and open up their service to customer pen testing – as a result their systems are almost continuously pen tested throughout the year. The Future is going to be Faster – and Appsec will have to be too In his presentation “Application Security at DevOps Speed and Portfolio Scale” at the same OWASP Appsec conference, Jeff Williams asserted that “Our traditional techniques for doing Appsec are failing, they’re crumbling at the edges”. Appsec has to speed up, become more flexible and Agile in itself. Because the future is going to keep getting faster. Software development projects are getting smaller and simpler and more organizations are adopting Agile methods because smaller, Agile projects are less likely to fail and they get to market much faster. Devops, Continuous Delivery and Continuous Deployment, Kanban, the Lean Startup approach of building a Minimum Viable Product quickly and getting it out for feedback, and other ideas about how to deliver more working software faster and cheaper are becoming mainstream. In order for Appsec to “push left” into the SDLC, Appsec has to change its role from assurance/auditing and compliance to proactively enabling self-service secure development. We have to stop pretending that big security reviews and stage gates at major project milestones still work (if they ever did). They need to be replaced by lightweight, in-phase, iterative and incremental preventative controls – simple cheap things that make sense to developers and that they can do as part of designing and building software. There’s still a role for pen testing and other security reviews. But not as a once-a-year annual release certification/assurance step to “prove that the system is secure” or some other fantasy. Pen tests and other reviews are just another source of feedback to the team, information that they can use to learn and adapt and improve. Security reviews need to be cheaper and scaled down, so that they fit into time boxes and so that they can be done earlier and more often. Security has to be fit into unit testing and Continuous Integration and Continuous Delivery and the other tight, continuous feedback loops that Agile teams rely on, using tools that don’t need to be understood and run by security experts and that fit with how developers think and work. There are a handful of organizations that are pushing Appsec further into the rapidly blurring lines between development and operations: Etsy, Netflix, and Twitter are already doing Appsec at “DevOps Speed” today, inventing new tools and ideas. The rest of Appsec has to catch up, or be left behind. BTW: If you are involved in security for your organization’s software, the SANS Institute would appreciate your insight. Please participate in the SANS Application Security Survey. The survey closes December 20.

To uncover insights into underlying patterns, organizations need to employ more sophisticated data analytics techniques and tools.

Agile - What’s a Manager to Do? As a manager, when I first started learning about Agile development, I was confused by the fuzzy way that Agile teams and projects are managed (or manage themselves), and frustrated and disappointed by the negative attitude towards managers and management in general. Attempts to reconcile project management and Agile haven't answered these concerns. The PMI-ACP does a good job of making sure that you understand Agile principles and methods (mostly Scrum and XP with some Kanban and Lean), but is surprisingly vague about what an Agile project manager is or does. Even a book like the Software Project Manager’s Bridge to Agility, intended to help bridge PMI's project management practices and Agile, fails to come up with a meaningful job for managers or project managers in an Agile world. In Scrum (which is what most people mean when they say Agile today), there is no place for project managers at all: responsibilities for management are spread across the Product Owner, the Scrum Master and the development team. We have found that the role of the project manager is counterproductive in complex, creative work. The project manager’s thinking, as represented by the project plan, constrains the creativity and intelligence of everyone else on the project to that of the plan, rather than engaging everyone’s intelligence to best solve the problems. In Scrum, we have removed the project manager. The Product Owner, or customer, provides just-in-time planning by telling the development team what is needed, as often as every month. The development team manages itself, turning as much of what the product owner wants into usable product as possible. The result is high productivity, creativity, and engaged customers. We have replaced the project manager with the Scrum Master, who manages the process and helps the project and organization transition to agile practices. Ken Schwaber, Agility and PMI, 2011 Project Managers have the choice of becoming a Scrum Master (if they can accept a servant leader role and learn to be an effective Agile coach – and if the team will accept them) or a Product Owner (if they have deep enough domain knowledge and other skills), or find another job somewhere else. Project Manager as Product Owner The Product Owner is command-and-control position responsible for the “what” part of a development project. It's a big job. The Product Owner owns the definition of what needs to be built, decides what gets done and in what order, approves changes to scope and makes scope / schedule / cost trade-offs, and decides when work is done. The Product Owner manages and represents the business stakeholders, and makes sure that business needs are met. The Product Owner replaces the project manager as the person most responsible for the success of the project (“the one throat to choke”). But they don’t control the team’s work, the technical details of who does the work or how. That’s decided by the team. Some project managers may have the domain knowledge and business experience, the analytical skills and the connections in the customer organization to meet the requirements of this role. But it’s also likely to be played by an absentee business manager or sponsor, backed up by a customer proxy, a business analyst or someone else on the team without real responsibility or authority in the organization, creating potentially serious project risks and management problems. Some organizations have tried to solve this by sharing the role across two people: a project manager and a business analyst, working together to handle all of the Product Owner’s responsibilities. Project Manager as Scrum Master It seems like the most natural path for a project manager is to become the team’s Scrum Master, although there is a lot of disagreement over whether a project manager can be effective – and accepted – as a Scrum Master, whether they will accept the changes in responsibilities and authority, and be willing to change how they work with the team and the rest of the organization. The Scrum Master is a “process owner” and coach, not a project manager. They help the team – and the Product Owner – understand how to work in an Agile process framework, what their roles and responsibilities are, set up and guide the meetings and reviews, and coach team members through change and conflict. The Scrum Master works a servant leader, a (nice) process cop, a secretary and a gofer. Somebody who supports the team and the Product Owner, “carries food and water” for them, tries to protect them from the world outside of the project and helps them solve problems. But the Scrum Master has no direct authority over the project or the team and does not make decisions for them, because Agile teams are supposed to be self-directing, self-organizing and self-managing. Of course that’s not how things start off. Any group of people must work their way through Tuckman’s 4 stages of team development: Forming-Storming-Norming-Performing. It’s only when they reach the last stage that a group can effectively manage themselves. In the mean time, somebody (the Scrum Master / Coach) has to help the team make decisions that they aren’t ready to make on their own. It can take a long time for a team to reach this point, for people to learn to trust each other – and the organization – enough. And it may not last long, before something outside of the team’s control sets them back: a key person leaving or joining the team, a change in leadership, a shock to the project like a major change in direction or cuts to the budget. Then they need to be led back to a high performing state again. Coaching the team and helping them out can be a full-time job in the beginning. After the team has got together and learned the process? Not so much. Which is why the Scrum Master is sometimes played part-time by a developer or sometimes even rotated between people on the development team. But even when the team is performing at a high level, there’s more to managing an Agile project than setting up meetings, buying pizza and trying to stay out of the way. I've come to understand that Agile doesn't make a manager’s job go away. If anything, it expands it. Managing Upfront First, there’s all of the work that has to be done upfront at the start of a project – before Iteration Zero. Identifying stakeholders. Securing the charter. Negotiating the project budget and contract terms. Understanding and navigating the organization’s bureaucracy. Figuring out governance and compliance requirements and constraints, what the PMO needs. Working with HR, line managers and functional managers to put the team together, finding and hiring good people, getting space for them to work in and the tools that they need to work with. Lining up partners and suppliers and contractors. Contracting and licensing and other legal stuff. >/p> The Product Owner might do some of this work - but they can't do it all. Managing Up and Out Then there’s the work that needs to be managed outside of the team. Agile development is insular, insulated and inward-looking. The team is protected from the world outside so they can focus on building features together. But the world outside is too important to ignore. Every development project involves more than designing and building software – often much more than the work of development itself. Every project, even a small project, has dependencies and hand-offs that need to be coordinated with other teams in other places, with other projects, with specialists outside of the team, with customers and partners and suppliers. There is forward planning that needs to be done, setting and tracking drop-dead dates, defining and maintaining interfaces and integration points and landing zones. Agile teams move and respond to change quickly. These changes can have impacts outside of the team, on the customer, other teams and other projects, other parts of the organization, suppliers and partners. You can try using a Scrum of Scrums to coordinate with other Agile teams up to a point, but somebody still has to keep track of dependencies and changes and delays and orchestrate the hand-offs. Depending on the contracting model and your compliance or governance environment, formal change control may not go away either, at least not for material changes. Even if the Product Owner and the team are happy, somebody still has to take care of the paperwork to stay onside of regulatory traceability requirements and to stay within contract terms. There are a lot of people who need to know what’s going on in a project outside of the development team – especially in big projects in big organizations. Communicating outwards, to people outside of the team and outside of the company. Communicating upwards to management and sponsors, keeping them informed and keeping them onside. Task boards and burn downs and big visible charts on the wall might work fine for the team, but upper management and the PMO and other stakeholders need a lot more, they need to understand development status in the overall context of the project or program or business change initiative. And there’s cost management and procurement. Forecasting and tracking and managing costs, especially costs outside of development labor costs. Contracts and licensing need to be taken care of. Stuff needs to be bought. Bills need to be paid. Managing Risks Scrum done right (with XP engineering practices carefully sewed in) can be effective in containing many common software development risks: scope, schedule, requirements specification, technical risks. But there are other risks that still need to be managed, risks that come from outside of the team: program risks, political risks, partner risks and other logistical risks, integration risks, data quality risks, operational risks, security risks, financial risks, legal risks, strategic risks. Scrum purposefully has many gaps, holes, and bare spots where you are required to use best practices – such as risk management. Ken Schwaber While the team and the Product Owner and Scrum Master are focused on prioritizing and delivering features and resolving technical issues, somebody has to look further out for risks, bring them up to the team, and manage the risks that aren't under the team’s control. Managing the End Game And just like at the start of a project, when the project nears the end game, somebody needs to take care of final approvals and contractual acceptance, coordinate integration with other systems and with customers and partners, data setup and cleansing and conversion, documentation and training. Setting up the operations infrastructure, the facilities and hardware and connectivity, the people and processes and tools needed to run the system. Setting up a support capability. Packaging and deployment, roll out planning and roll back planning, the hand-off to the customer or to ops, community building and marketing and whatever else is required for a successful launch. Never mind helping make whatever changes are required to business workflows and business processes that may be required with the new system. Project Management doesn't go away in Agile There are lots of management problems that need to be taken care of in any project. Agile spreads some management responsibilities around and down to the team, but doesn’t make management problems go away. Projects can’t scale, teams can’t succeed, unless somebody – a project manager or the PMO or someone else with the authority and skills required – takes care of them.

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