It's a common dilemma: You host multiple Web-accessible applications, for both internal customers and external users. A few of your developers are keeping up on the last programming trends and security models, while some of your highest-seniority employees are stuck in programming models outdated a decade ago. You've got a hodgepodge of access and authentication methods, along with a lot of client-server interaction, and a little bit of Web services and SOA, as well as Citrix or Terminal Services thrown in. There are even a few people still dialing in on phone lines to access dumb terminal-based applications.
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Truth be told, if someone asked what you thought of the situation, you'd reply it's a deck of cards just waiting to be pushed over by the right inquisitive hacker. You've got to get control of your applications and authentication models, so where do you start and what do you do? There are six broad areas that you'll need to address: education, strategy, standardization, policies, remediation, and retirement.
The first step is to educate everyone about the problem. Many of your coworkers and members of management may not be aware of your dilemma. Sure, you've groaned about it here and there, but it hasn't become a top-level concern. It isn't even on the list of things your boss is worried about. It's time to elevate the issue. Develop a cohesive, thoughtful paper on the current situation, the problem, and steps toward a solution, then present it to your supervisor. Do it out of the blue, and you'll even score points with the boss.
The second step is to educate people about the various authentication components. Essentially, you want to explain identity, authentication, authorization, and access control (and accounting/auditing), or simply AAA, as parts of a systematic process, each of which can be accomplished using various methods.
And you want to push for more maturity on each of those concepts. If single users end up with multiple identities, you need an identity management system (or maybe federated identities, if multiple companies are involved). You want to move authentication from passwords to something more sophisticated, such as two-factor authentication. You want to move access control from Discretionary Access Controls (DAC) to client-server impersonation and eventually Role-Based Access Control (RBAC).
Finally, the data you protect must be categorized according to sensitivity and protected accordingly. The idea is to get staff and management thinking about the process, or processes, in a strategic manner -- to move away from individual silo thinking.
Once the boss realizes there's a real problem, it's time to create an overall guiding strategy. Say something like, "Decrease overall computer costs and security risk by designing strong data controls." (Wow, that almost hurt to think of, drawing back on my Dilbert-like days in management, where you have to say almost nothing to accomplish something.)
The idea is to make the problem a strategy. Your boss and your boss' boss can't act until you've developed a strategy and, more than likely, tied that strategy to existing business objectives. From the strategy, build tactical methods to accomplish it.