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Foundations of Mac OS X Leopard Security

jsuda writes "At least a half-dozen times in the book 'Foundations of Mac OS X Leopard Security' the authors state that there is a misconception that the Macintosh computer is immune from security problems. That allegation may explain why there are very few books published (and nearly none in recent years) about security for the Mac. This book is meant to change all that. The authors acknowledge that the Mac OS X software has had little of the security problem experience of Windows (and other operating systems, to a lesser extent) but they spend 455 pages detailing exactly where and how the Macintosh platform is (or may be) vulnerable." Read below for the rest of Jsuda's review. Foundations of Mac OS X Leopard Security author Charles S. Edge, Jr., William Barker, and Zack Smith pages 455 publisher Apress rating 9 reviewer jsuda ISBN 978-1-59059-989-1 summary Best book on Mac Security Many of the security issues raised in the book are theoretical or deal with added elements of the Mac software install that contain non-Apple components — Apache Web server and Perl and PHP scripting packages, for example. Many of the items of concern deal with generic problem areas of computer usage in general, both software and hardware, which affect the Mac as well as any other computers and networks. While the perspective of the book is on the Mac, much of the security review will apply to any type of computer or network.

Messieurs Edge, Barker, and Smith are seasoned Mac and security professionals who point out in a very systematic and comprehensive way the potential problems of running the Mac both in single use and networked environments. The focus is primarily on Mac OS X Leopard and the other software which comes with any new Mac computer, although there is some discussion of earlier OS X versions and earlier generations of Apple applications like Airport.

The book has five main parts covering general security matters, essential security fundamentals, networking, sharing, and workplace security issues. There are four very short appendices of modest value.

The initial first three chapters deal with general security and security fundamentals is basic stuff discussing how technical computer security issues are entwined with practical realities of using computers in a business or home, and that compromises between security and practicality generally must be made. There is discussion of types of security attacks, how the Windows booting programs, Parallels and Boot Camp, implicate Windows security issues on the Mac, and how the UNIX underpinnings of the Mac OS X allow for more sophisticated techniques and tools in securing the Mac computer and networks. Chapter 1 is a useful "quick start" guide of items which can be addressed readily by nearly any level of user to safeguard the Mac from many security concerns. Apple has provided a lot of built-in security features and services which can be adjusted by individual users to his or her own needs, like FileVault, Secure Trash, Keychain, permissions, and others. Higher-level users and maybe experienced security professionals not used to the Mac may be bored with the first part of the book.

Part two deals with protecting the Mac from malware and exploitable services in the OS and major applications like the Safari browser and Mail applications. It explains how malware can affect the Mac through script viruses, social engineering techniques, and other exploits. The book lists a number of available software tools which can help solve some of the potential problems. The section on reviewing and configuring monitoring processes and logs is especially interesting.

Securing networks, using and configuring firewalls, and wireless networking make up the bulk of part three. The content in chapters 7 through 9 is quite technical covering types of networks; routers, hubs and switches;proxy, DMZ, and other servers and hardware setups, advanced firewall configuration using both GUI and command line interfaces; filtering; traffic throttling; and more. The sections describing testing of firewalls and hacking wireless networks using tools like Kismac and iStumbler are especially useful.

Chapter 11, in part four, dealing with website security when utilizing the built-in Apple web services, includes a checklist of at least a dozen items to be dealt with in locking down a site. Security for remote conductivity is addressed also, with particular emphasis given to VPN, secure shell, and the use of network administration tools like Timbuktu and DAVE. Attention is given to both the standard Mac OS X installation as well as to OS X Server. The most complex discussions involve using Open Directory in a security plan. My favorite sections were in chapters 14 on network scanning, monitoring, and intrusion prevention tools. The book describes how to understand your own machine/network security status by learning how to attack other networks. And how to use techniques like white/black box testing, fingerprinting, enumeration, port and TCP/UDP scans, ping sweeps, and more.

The book describes how intrusion detection is accomplished. Guidance is provided on software tools like Tripwire, snort, Checkmate, and others. The last chapter concerns forensics and how to handle attempted or successful intrusions to both understand security weaknesses and to preserve evidence for civil or criminal proceedings, CSI-like.

Nearly all of the presentations cover two levels of interactivity using either GUI-based tools or the command line. Except for a handful of sections, the presentations are useful even for higher-end users, including those dealing with medium to large networks.

The writing is workmanlike and without style or wit, but carefully organized and expressed. There are plenty of (grayscale) screenshots of relevant software application configurations, and sidebar Notes and Tips on many topics. Anyone who has a serious interest in Mac OS X security will benefit from this book as its main virtue is its systematic and comprehensive approach to the issues. It is designed to inform users of all levels how and why to think about OS X security. Geeks who want or need to know Mac OS X security will get a nicely organized book sufficiently filled with useful content. This is not a book intended to raise all security issues or to provide all the answers. It does answer many problems, and will point nearly all users in the right direction for their specific needs.

You can purchase Foundations of Mac OS X Leopard Security from amazon.com. Slashdot welcomes readers' book reviews -- to see your own review here, read the book review guidelines, then visit the submission page.

16 of 213 comments (clear)

  1. A good start to the discussion by jeiler · · Score: 5, Insightful

    OSX is intrinsically far more secure than Windows, but all systems have their vulnerabilities. For Mac pros to acknowledge that "far more secure" does not equal "completely secure" is a good step in the right direction. Thanks for the review, jsuda.

    --

    If you haven't been down-modded lately, you aren't trying.

    Sacred cows make the best hamburger.

    1. Re:A good start to the discussion by negRo_slim · · Score: 5, Insightful

      OSX is intrinsically more secure than Windows There fixed that for you. Let us not forget Windows also faces much more exposure due to it's market share. But then again anything that's not locked in a room with no network access is going to be vulnerable to one degree or another.
      --
      On the Oregon Cost born and raised, On the beach is where I spent most of my days
    2. Re:A good start to the discussion by Anonymous Coward · · Score: 5, Interesting

      OS X has a solid architecture, but all the evidence indicates that Apple has not taken security seriously as a process issue to the same extent that Microsoft has.

      Some of the recent bugs with Safari remind me of the stuff MS was doing 10 years ago, where junior programers hacked together E-Z features without any consideration for the security implications.

      The other issue is that QuickTime is a huge smelly bug-filled legacy turd, but thankfully Apple has announced that they are rewriting a replacement.

    3. Re:A good start to the discussion by neil-ngc · · Score: 4, Interesting

      It's hard to write much about security holes when there isn't much of a history of attacks. Can we say "OSX is intrinsically more secure?" Maybe, certainly a lot of its default configuration tend to be more secure than Windows' defaults.

      But what's made, and perpetuated, the notion that Macs are immune to viruses and other attacks is that there just aren't very many of them out there. Even with Mac's quickly growing market share, it's still far more lucrative to target mass market windows machines.

    4. Re:A good start to the discussion by The+Ultimate+Fartkno · · Score: 4, Funny

      but all systems have their vulnerabilities. *shocked gasp!*

      villager: Look, Slashdot, look! A heretic!

      *rumblerumblerumble*

      unix mob: BIND HIM TO A SERVER RACK WITH CAT-5 AND BURN HIM!

      dissenter #1: We can't!

      unix mob: Why not?

      dissenter #2: Halon fire suppression system in the room!

      *natternatternatter*

      unix mob: Make him use Windows...

      jeiler: Do your worst!

      unix mob: ...VISTA!

      jeiler: NOOOOOOOOOOOOOOOO!!

    5. Re:A good start to the discussion by jeiler · · Score: 4, Insightful

      OSX is intrinsically more secure than Windows There fixed that for you. Let us not forget Windows also faces much more exposure due to it's market share.

      I'm aware that Window's market share makes them the "low-hanging fruit," but even without considering market share, OSX has fewer security holes than Windows.

      Most of the difference seems (to me, YMMV) to be remnants of OSX's background in BSD, and the security practices in the BSD world--it seems that Apple has added far more functionality to BSD, but at a cost of lowered security.

      But then again anything that's not locked in a room with no network access is going to be vulnerable to one degree or another.

      Don't forget to unplug it, too! :D

      --

      If you haven't been down-modded lately, you aren't trying.

      Sacred cows make the best hamburger.

    6. Re:A good start to the discussion by jeiler · · Score: 5, Insightful

      How can you say that with any certaintity when you don't have the worlds underground hammering at your door every day for years on years?

      By comparing the structure and functionality. If we had to wait until a system has been attacked to see how vulnerable it was, we'd all be in REAL trouble.

      One basic factor is default user account privileges: Microsoft has all new users default to Admin privileges (a practice that may have stopped with Vista), while Apple (like Linux) has new users default as limited accounts that must be escalated to have Admin. Microsoft's way is more handy (in that even an inexperienced computer owner can set up an account that can do anything), but insecure (because only an inexperienced computer owner would WANT all users to have accounts that can do anything).

      There are plenty of vulnerabilities on both sides, but from everything I've seen in 20+ years of working with both Microsoft and Apple products, Apple is in the lead for security. Of course, that may change without notice, if Microsoft tightens up their practices, or Apple adds more vulnerabilities.

      --

      If you haven't been down-modded lately, you aren't trying.

      Sacred cows make the best hamburger.

    7. Re:A good start to the discussion by prockcore · · Score: 4, Interesting

      What, intrinsically, makes OSX immune to spyware?

      OSX cannot stop you from running software that is inherently evil.

      The fact that there isn't spyware on OSX proves that small marketshare is indeed a huge factor in lack of exploits in OSX... because there is absolutely no technical reason for spyware not to work on OSX.

    8. Re:A good start to the discussion by geekoid · · Score: 4, Insightful

      You poise a logical fallacy.

      "Let us not forget Windows also faces much more exposure due to it's market share. "

      I order for that to be a factor worth considering, the OSes must be designed with the same architecture, management, coder skill, etc. . . .

      The MAc has not been in a locked room with no network, there are many groups of people trying to find remote flaws all the time, with almost no success. And the success they did had relied on 3rd party hardware and drivers.

      While I understand it's not perfect, it is far better then Windows by design, and it is reflected in the many tests groups outside of Apple do every day.

      Insightful my ass.

      --
      The Kruger Dunning explains most post on /. http://en.wikipedia.org/wiki/Dunning%E2%80%93Kruger_effect
  2. Look at how they are attacked. by khasim · · Score: 4, Interesting

    But what's made, and perpetuated, the notion that Macs are immune to viruses and other attacks is that there just aren't very many of them out there.
    No. With the Internet, attacks can be automated.

    Put an unpatched WinXP on the Internet and watch how quickly it is cracked by an automated process randomly scanning IP blocks.

    Even with Mac's quickly growing market share, it's still far more lucrative to target mass market windows machines.
    So you'd turn down $5 million for a chance at a portion of $90 million?

    No. If they were easy to crack, they would be cracked. Automatically. By a zombie scanning IP blocks.

    Can we say "OSX is intrinsically more secure?" Maybe, certainly a lot of its default configuration tend to be more secure than Windows' defaults.
    The real issue is that Macs are very secure ON THEIR OWN. Not in relation to anything else.

    Today, most boxes are cracked via worms, browser exploits and email attachments.

    Removing entire avenues of attack is possible with a Mac. Remove an avenue of attack and you've increased your security.

    Then, as long as the DIS-INFECTION rate is HIGHER than the INFECTION rate, those systems will be "secure". At least, they will not be cracked by worms, browser exploits or email attachments.

    1. Re:Look at how they are attacked. by Sparks23 · · Score: 5, Insightful

      Well...

      Mac OS X has some advantages in security. But I can't really say those advantages are due to Apple being somehow inherently 'better' coders than Microsoft or having made some kind of perfect system.

      In my opinion, Mac OS X is less vulnerable than Windows in many areas is due to Apple being willing to go 'okay, this particular technology is dead, move along.' Microsoft relies on backwards compatibility for large market share; break backwards compatibility, and people do not upgrade. (Case in point: Vista.)

      Apple has a smaller market share (and speaking as a Mac user and developer, we tend to sort of go, 'yes please, whatever you say' when they want to change things). We might bitch about it periodically (whither thou, 64-bit Carbon?), but this gives them the freedom to throw out legacy code and simplifies the code maintenance.

      Or, in short: Apple's coders are not inherently better, but they end up with less old cruft to support and try to be aware of.

      As a case in point, I'll note that the worst offender in terms of security on Mac OS X has, historically, been Quicktime. Quicktime is perhaps the oldest, most legacy-laden bit of crud in Apple's library. (The Quicktime APIs are darn near prehistoric, especially compared to things like CoreImage et al.) One would assume this means that Quicktime, more than almost anything else, has chunks of code that predate most of the programmers working on it, and which no one remembers or thinks about.

      And in my experience, that's often where those kind of bugs come from... you change something, add a new bit of code that passing something into a function somewhere, completely unaware that four levels deeper there's some function which assumes the buffer is only 4k long. The old programmers knew there was an implicit limit down in this ancient routine, but no one now knows of that limit, and so -- unaware of this lurking nightmare 5 levels deeper in the stack -- they pass in a 6k buffer. Boom, security issue.

      Windows has this problem in almost every corner of the OS. Worse, they cannot readily get around it... you can't just rewrite things from scratch, or you break legacy support! But as a result, there often are quite a few lurking behaviors that newer coders aren't aware of somewhere deeper in the system, things that never got documented, and which will eventually reach out to bite them.

      Sure, there's situations which are just plain dumb (the carpet-bombing attack, for instance, is inexcusable behavior on IE's part), but most of those seem to be the minority.

      So, yeah, Mac OS X has some advantage, as they have less legacy stuff to deal with. But even with that sort of advantage, no operating system -- not even Linux! -- is completely free of all flaws. We as users need to accept as a given that almost nothing is completely secure (at least, not and still be usable). This is especially true when many viruses and trojans rely on social engineering.

      Even if Mac OS X prompts the user before allowing a program to elevate privileges, does that matter if users just click without looking? After all, lots of programs prompt for such things in order to install some shared framework they use at the installation or first-run stage. I know a lot of Mac users who just click on that warning blindly. And the warning doesn't matter if the user doesn't really pay attention.

      So, yeah. Mac OS X may have less tangled, jungle-like legacy code for scary security holes to lurk in, but that does not mean it is invulnerable. Certainly not immune even to automated bugs, and especially not immune from social engineering.

      Because the biggest security hole -- on ANY operating system -- is often user behavior.

      There's my $0.02, anyway. :)

      --
      --Rachel
  3. Wrong reason by MBCook · · Score: 5, Insightful

    That allegation may explain why there are very few books published (and nearly none in recent years) about security for the Mac.

    I don't think that's it at all. It's there is very little market for OS X security books at this point. Most people don't care. Let me explain.

    On the home end of things, Macs are great and relatively secure. They do fine. That said, how many people buy books on Windows Security for those home computers? I'm going to say very few. Most people don't care or don't know they should do something to increase security.

    The other front is businesses. Most businesses don't use Macs, by a large margin. Macs have a smaller enterprise market share than overall market share. If you are asked to secure a server or desktop, chances are it will be Windows or Linux.

    These kind of books are, for the most part, targeted at administrators, businesses, etc. Since that market (administrators of Macs) is so small (compared to administrators of Windows boxes) there are very few books written.

    This is compounded by the most important boxes to secure: web facing boxes (like servers). OS X Server's market share is very tiny compared Windows and Linux.

    The books aren't there because the demand for them isn't very big, not because Mac users are think they are invulnerable from arrogance.

    --
    Comment forecast: Bits of genius surrounded by a sea of mediocrity.
  4. The Fullest Measure by SuperKendall · · Score: 4, Insightful

    Take 'em all down, Fanboi! Good dog!

    And with that message, your contentless response to a well-written message puts on display the fullest measure of your intelligence.

    --
    "There is more worth loving than we have strength to love." - Brian Jay Stanley
  5. Re:You're wrong. by xaxa · · Score: 4, Interesting

    And I'm saying that an environment of 5 million machines WOULD be exploited if it COULD be exploited. We have proof of that: just look at the unpatched Linux servers (running crappy forum software which has been exploited) controlling botnets etc (chosen because they have good network connections and aren't often turned off).
  6. The attitude of Mac users is what worries me by theolein · · Score: 5, Interesting

    I own four macs and am a sysadmin to a company running about 45 macs. I really like Mac OSX as an OS, as it is generally very robust and flexible, and, in my experience, the OS contains many features that make it both more productive and secure than Windows.

    That, however, is a generalisation. Windows has made strides to improve its security record and Vista is much better in this respect than XP was (even if one does get the feeling that a lot of Vista functionality was "bolted on" after the fact). I would be wary of making wild claims about Vista being less secure than OSX, but I think, in general, Apple's use of ACLs in 10.5, coupled with other security features do give it a slight edge.

    That said, the exploit this week about the Applescript ARDAgent vulnerability, and above all, the general reaction of Mac users to this vulnerability, and again as expressed in this slashdot comments section, coupled with my experiences with my users at work shows me a few things:

    Mac users in general, tend to hold on to myths and marketing claims put out by Apple's PR more that users of other platforms do. I honestly think that the Mac vs. PC ads do Mac users a disservice because so many belive the claims without even asking any questions about them. An example: PC is frustrated because Mac now has Office 2008 which can do all that Office 2007 can. This is simply false. Office 2008 lacks VBA for one thing, lacks conditional formatting in Excel for another, and is so slow, it is barely usable on a new Mac Pro tower. Our older Office version, Office v.X runs faster in Rosetta emulation.

    Another example. Coincidentally, I discovered this week that Apple Mail will run a Mac application thta has been attached to an email directly out of Mail. It will warn you, twice, about this, but Windows warns you about new apps as well that hasn't stopped millions of clueless end users ignoring the warnings and just clicking away. I did a few tests on users at work and they *all* opened the app. An app, combined with the applescript ARDAgent exploit would be an excellent way for an attacker to install a trojan for phishing or zombie purposes.

    The atttude of Mac users that the platform is magically secure than Windows (it is more secure than XP, but not much more than Vista if at all) in the same way that Mac users were still crowing about Win98 BSODs the same way Windows users were crowing about OS9 crashing all over the place, years after neither one was used very much any more, is indicative of the problems that we, the Mac using community will face when malware exploits start to gather pace on the Mac.

    I honestly believe that the Mac has been mostly protected by its small marketshare up until now. Most exploits come out of China and Russia, and most malware authors there do not have Macs. That will eventually change.

    I say that Mac users should be less confident in the platform and more aware of security. I suspect that in 5 years, Anti-Virus software will also be a mainstay on OSX.

  7. Full of shit by RzUpAnmsCwrds · · Score: 4, Insightful

    DISCLAIMER: I work at Microsoft.

    Pretty much everyone who posts about this is full of shit.

    Vista has had 34 vulnerabilities over the last 1.5 years. That's less than Mac OS X over the same period.

    If you want to argue that Mac OS X is "more secure", you need to do it on grounds other than vulnerabilities. At best, Mac OS X and Vista are similar in the number and severity of vulnerabilities.

    So the new big thing on Slashdot, since the vulnerability statistics don't back up the "more secure" argument, is to argue that Mac OS is "intrinsically" more secure than Windows.

    I have no idea what people are talking about there. Vista has ACLs, just like Mac OS X. Vista has sudo (UAC in Vista), just like Mac OS X. Vista disables network-facing services by default, just like Mac OS X. Vista has a firewall, just like Mac OS X.

    So, you can wave your hands and say that Mac OS X is secure because it's "UNIX". But I'm not impressed. There's nothing "intrinsically" secure about UNIX compared to any other modern OS.

    What I can say is that Apple doesn't take security bugs seriously. Microsoft acknowledges when there is a reported vulnerability and reports when a fix is delivered. Apple pretends that vulnerabilities don't exist. Apple sometimes stealth-patches vulnerabilities away. And Apple frequently tries to downplay the severity of vulnerabilities.

    Take, for example, the root privilege escalation vulnerability reported several days ago in Mac OS X. That kind of bug is extremely serious, yet we had 20 people on Slashdot commenting about how it's not a big deal. Apple hasn't even acknowledged that there's a problem.