{"id":309,"date":"2017-12-29T14:22:59","date_gmt":"2017-12-29T14:22:59","guid":{"rendered":"https:\/\/bootstrap-it.com\/blog\/?p=309"},"modified":"2018-01-25T03:03:05","modified_gmt":"2018-01-25T03:03:05","slug":"penetration-testing-choosing-the-right-linux-tool-stack-to-fix-your-broken-it-security","status":"publish","type":"post","link":"https:\/\/bootstrap-it.com\/blog\/?p=309","title":{"rendered":"Penetration testing: choosing the right (Linux) tool stack to fix your broken IT security"},"content":{"rendered":"<div id=\"s-share-buttons\" class=\"horizontal-w-c-circular s-share-w-c\"><a href=\"http:\/\/www.facebook.com\/sharer.php?u=https:\/\/bootstrap-it.com\/blog\/?p=309\" target=\"_blank\" title=\"Share to Facebook\" class=\"s3-facebook hint--top\"><\/a><a href=\"http:\/\/twitter.com\/intent\/tweet?text=Penetration testing: choosing the right (Linux) tool stack to fix your broken IT security&url=https:\/\/bootstrap-it.com\/blog\/?p=309\" target=\"_blank\"  title=\"Share to Twitter\" class=\"s3-twitter hint--top\"><\/a><a href=\"http:\/\/reddit.com\/submit?url=https:\/\/bootstrap-it.com\/blog\/?p=309&title=Penetration testing: choosing the right (Linux) tool stack to fix your broken IT security\" target=\"_blank\" title=\"Share to Reddit\" class=\"s3-reddit hint--top\"><\/a><a href=\"http:\/\/www.linkedin.com\/shareArticle?mini=true&url=https:\/\/bootstrap-it.com\/blog\/?p=309\" target=\"_blank\" title=\"Share to LinkedIn\" class=\"s3-linkedin hint--top\"><\/a><a href=\"mailto:?Subject=Penetration%20testing:%20choosing%20the%20right%20(Linux)%20tool%20stack%20to%20fix%20your%20broken%20IT%20security&Body=Here%20is%20the%20link%20to%20the%20article:%20https:\/\/bootstrap-it.com\/blog\/?p=309\" title=\"Email this article\" class=\"s3-email hint--top\"><\/a><\/div><div class=\"section-inner sectionLayout--insetColumn\">\n<p id=\"e62b\" class=\"graf graf--p graf-after--h3\">Got IT infrastructure? Do you know how secure it is? The answer will probably hurt, but this is the kind of bad news you\u2019re better off getting sooner rather than later.<\/p>\n<p id=\"9d38\" class=\"graf graf--p graf-after--p\">The only reasonably sure way to find out what\u2019s going on with your servers is to apply a solid round of penetration testing. Your ultimate goal is to uncover any dangerous vulnerabilities so you can lock them down.<\/p>\n<p id=\"c1eb\" class=\"graf graf--p graf-after--p\">By \u201cdangerous vulnerability\u201d I mean obvious things like unprotected open ports and unpatched software. But I also mean the existence of freely available intelligence about your organization that\u2019s probably just floating around the internet, waiting to be collected and turned against you.<\/p>\n<p id=\"cbfe\" class=\"graf graf--p graf-after--p\">Pen testing is made up of three very different parts, each with its own unique tools and protocols.<\/p>\n<ul class=\"postList\">\n<li id=\"e4be\" class=\"graf graf--li graf-after--p\"><strong class=\"markup--strong markup--li-strong\">Passive information gathering<\/strong>, where testers scour the public internet looking for subtle hints or carelessly revealed private data that can be used against the organization.<\/li>\n<li id=\"6628\" class=\"graf graf--li graf-after--li\"><strong class=\"markup--strong markup--li-strong\">Active information gathering<\/strong>, where the organization\u2019s networks and servers are scanned for potential vulnerabilities.<\/li>\n<li id=\"a3d1\" class=\"graf graf--li graf-after--li\"><strong class=\"markup--strong markup--li-strong\">Identifying exploits<\/strong>\u00a0that could possibly be run against the organization\u2019s infrastructure.<\/li>\n<\/ul>\n<p id=\"93c7\" class=\"graf graf--p graf-after--li\">Let\u2019s look at those one at a time.<\/p>\n<h4 id=\"acdc\" class=\"graf graf--h4 graf-after--p\">Passive Information Gathering (OSINT)<\/h4>\n<p id=\"a809\" class=\"graf graf--p graf-after--h4\">Say your company has around 50 employees and a handful of outside contractors, each of whom is most likely active on both professional and personal social networks. And say you\u2019ve got the usual range of corporate and product websites and social media accounts (like LinkedIn).<\/p>\n<p id=\"eb7e\" class=\"graf graf--p graf-after--p\">Now pause for a moment and try to imagine that you\u2019re a hacker who\u2019s searching for exploitable information about your company which he can use to launch an attack. Assuming he\u2019ll stick exclusively to the public internet and not break any laws, how much do you think he\u2019ll find?<\/p>\n<p id=\"79bc\" class=\"graf graf--p graf-after--p\">Not too much? After all, no one is stupid enough to post passwords and account information to the internet, right?<\/p>\n<p id=\"cf30\" class=\"graf graf--p graf-after--p\">Perhaps. But you won\u2019t believe how easy it can be to use what\u00a0<strong class=\"markup--strong markup--p-strong\">is<\/strong>\u00a0there to figure out all the passwords and administration information that hackers will need to get what they\u2019re after. Don\u2019t believe me? Do some passive information gathering yourself.<\/p>\n<p id=\"acdd\" class=\"graf graf--p graf-after--p\">Among the fantastic\/frightening information gathering tools available to help you (which also include Maltego and Shodan) there\u2019s a great Linux-based open source package named Recon-ng\u200a\u2014\u200aabout which I created a\u00a0<a href=\"http:\/\/pluralsight.pxf.io\/c\/1191769\/424552\/7490?subId1=solving&amp;u=https%3A%2F%2Fapp.pluralsight.com%2Fprofile%2Fauthor%2Fdavid-clinton\">video course on Pluralsight<\/a>.<\/p>\n<p id=\"a684\" class=\"graf graf--p graf-after--p\">You start by providing Recon-ng with some information about your company and choosing the particular scans that interest you. All the hard work will then be done by tools they call\u00a0<em class=\"markup--em markup--p-em\">modules<\/em>. Each of the 90+ available modules is a script that reads data from the Recon-ng database and launches a scanning operation against some remote data resource.<\/p>\n<p id=\"4ec0\" class=\"graf graf--p graf-after--p\">Based on your choices, Recon-ng will intelligently comb through vast volumes of DNS, social media, and search engine results, plus information-rich position postings for new developers and hints to internal email addresses relating to your target. When it\u2019s done, the software will prepare a report that\u2019s guaranteed to scare the daylights out of you.<\/p>\n<\/div>\n<div class=\"section-inner sectionLayout--outsetColumn\">\n<figure id=\"8a52\" class=\"graf graf--figure graf--layoutOutsetCenter graf-after--p\" data-scroll=\"native\">\n<div class=\"aspectRatioPlaceholder is-locked\">\n<div class=\"aspectRatioPlaceholder-fill\"><\/div>\n<div class=\"progressiveMedia js-progressiveMedia graf-image is-canvasLoaded is-imageLoaded\" data-image-id=\"1*ib_cEOpbA0PrpyhFU_hOnA.png\" data-width=\"1280\" data-height=\"720\" data-action=\"zoom\" data-action-value=\"1*ib_cEOpbA0PrpyhFU_hOnA.png\" data-scroll=\"native\"><canvas class=\"progressiveMedia-canvas js-progressiveMedia-canvas\" width=\"75\" height=\"40\"><\/canvas><img decoding=\"async\" class=\"progressiveMedia-image js-progressiveMedia-image\" src=\"https:\/\/cdn-images-1.medium.com\/max\/1100\/1*ib_cEOpbA0PrpyhFU_hOnA.png\" data-src=\"https:\/\/cdn-images-1.medium.com\/max\/1100\/1*ib_cEOpbA0PrpyhFU_hOnA.png\" \/><\/div>\n<\/div><figcaption class=\"imageCaption\">A text-based report based on a few Recon-NG\u00a0scans<\/figcaption><\/figure>\n<\/div>\n<div class=\"section-inner sectionLayout--insetColumn\">\n<p id=\"c1e3\" class=\"graf graf--p graf-after--figure\">With this information, all a hacker would have to do is sift through the data and set the launch date for your attack. With this information, all\u00a0<strong class=\"markup--strong markup--p-strong\">you<\/strong>\u00a0will have to do is tighten up your defences and speak with your team about being a\u00a0<strong class=\"markup--strong markup--p-strong\">lot<\/strong>\u00a0more careful when communicating online.<\/p>\n<p id=\"f6d4\" class=\"graf graf--p graf-after--p\">That OSINT acronym I used above? It stands for Open Source Intelligence. Stuff anyone can get.<\/p>\n<h4 id=\"36fa\" class=\"graf graf--h4 graf-after--p\">Active information gathering (vulnerability assessment)<\/h4>\n<p id=\"ffc2\" class=\"graf graf--p graf-after--h4\">Besides all the things you thoughtlessly leave lying around across the internet, there\u2019s probably a lot more that a hacker can learn about your infrastructure from the infrastructure itself. If your servers are on a network, it\u2019s because, to some degree, you want them exposed to network users. But that might also expose things you\u2019d rather keep quiet, including the fact that you might be running software that\u2019s buggy and open for exploits.<\/p>\n<p id=\"5e37\" class=\"graf graf--p graf-after--p\">The good news is that government and industry players\u200a\u2014\u200alike the US government\u2019s NIST and their<a class=\"markup--anchor markup--p-anchor\" href=\"https:\/\/nvd.nist.gov\/\" target=\"_blank\" rel=\"noopener\" data-href=\"https:\/\/nvd.nist.gov\/\">\u00a0National Vulnerability Database<\/a>\u200a\u2014\u200ahave been actively tracking software vulnerabilities for decades now and they make their information freely available. The bad news is that their databases contain hundreds of thousands of those vulnerabilities and it makes for really dull reading.<\/p>\n<p id=\"7ccc\" class=\"graf graf--p graf-after--p\">You\u2019d like to be able to quickly and regularly scan your network and the devices attached to it to make sure there\u2019s nothing that needs patching, but it\u2019s just not humanly possible to do it manually. So forget humans. You\u2019re going to need software.<\/p>\n<p id=\"d40b\" class=\"graf graf--p graf-after--p\">Vulnerability scanners are software tools that automatically scan your network and servers for unpatched software, open ports, misconfigured services, and potential exploit vectors (like SQL injection or cross-site scripting). Generally, the software will handle the vulnerability data and search for any matches with what you\u2019ve got running. It\u2019s your job to define the target, set the scan types you want run, read the reports that come out the other end, and\u200a\u2014\u200amost important of all\u200a\u2014\u200afix whatever\u2019s broken.<\/p>\n<p id=\"ed62\" class=\"graf graf--p graf-after--p\">Commercial scanning packages with free tiers include Nessus, Nexpose, and Burp Suite. OpenVAS is a mature, fully open source tool that can handle just about anything you throw at it. And, most conveniently, it just so happens that my Pluralsight collection also includes a<a href=\"http:\/\/pluralsight.pxf.io\/c\/1191769\/424552\/7490?subId1=solving&amp;u=https%3A%2F%2Fapp.pluralsight.com%2Fprofile%2Fauthor%2Fdavid-clinton\">\u00a0video guide to using OpenVAS<\/a>.<\/p>\n<\/div>\n<div class=\"section-inner sectionLayout--outsetColumn\">\n<figure id=\"05b5\" class=\"graf graf--figure graf--layoutOutsetCenter graf-after--p\" data-scroll=\"native\">\n<div class=\"aspectRatioPlaceholder is-locked\">\n<div class=\"progressiveMedia js-progressiveMedia graf-image is-canvasLoaded is-imageLoaded\" data-image-id=\"1*yx5U_ewbTlDhTg8cafUpKw.png\" data-width=\"1280\" data-height=\"720\" data-action=\"zoom\" data-action-value=\"1*yx5U_ewbTlDhTg8cafUpKw.png\" data-scroll=\"native\"><canvas class=\"progressiveMedia-canvas js-progressiveMedia-canvas\" width=\"75\" height=\"40\"><\/canvas><img decoding=\"async\" class=\"progressiveMedia-image js-progressiveMedia-image\" src=\"https:\/\/cdn-images-1.medium.com\/max\/1100\/1*yx5U_ewbTlDhTg8cafUpKw.png\" data-src=\"https:\/\/cdn-images-1.medium.com\/max\/1100\/1*yx5U_ewbTlDhTg8cafUpKw.png\" \/><\/div>\n<\/div><figcaption class=\"imageCaption\">The results page of an OpenVAS scan\u200a\u2014\u200ausing their Greenbone browser interface<\/figcaption><\/figure>\n<\/div>\n<div class=\"section-inner sectionLayout--insetColumn\">\n<p id=\"293b\" class=\"graf graf--p graf-after--figure\">An outstanding platform for running all kinds of scans and testing is the Kali Linux distribution. Kali, which itself is highly secure by default, comes with dozens of networking and security software packages pre-configured. OpenVAS, while easily installed to Kali, was left out of the default profile due to its size.<\/p>\n<\/div>\n<div class=\"section-inner sectionLayout--outsetColumn\">\n<figure id=\"821f\" class=\"graf graf--figure graf--layoutOutsetCenter graf-after--p\" data-scroll=\"native\">\n<div class=\"aspectRatioPlaceholder is-locked\">\n<div class=\"progressiveMedia js-progressiveMedia graf-image is-canvasLoaded is-imageLoaded\" data-image-id=\"1*-1tXkgo5vsqGiieo31YBhg.png\" data-width=\"1024\" data-height=\"815\" data-is-featured=\"true\" data-action=\"zoom\" data-action-value=\"1*-1tXkgo5vsqGiieo31YBhg.png\" data-scroll=\"native\"><canvas class=\"progressiveMedia-canvas js-progressiveMedia-canvas\" width=\"75\" height=\"59\"><\/canvas><img decoding=\"async\" class=\"progressiveMedia-image js-progressiveMedia-image\" src=\"https:\/\/cdn-images-1.medium.com\/max\/1100\/1*-1tXkgo5vsqGiieo31YBhg.png\" data-src=\"https:\/\/cdn-images-1.medium.com\/max\/1100\/1*-1tXkgo5vsqGiieo31YBhg.png\" \/><\/div>\n<\/div><figcaption class=\"imageCaption\">Some pen-testing-friendly software packages available in Kali Linux right out of the\u00a0box<\/figcaption><\/figure>\n<\/div>\n<div class=\"section-inner sectionLayout--insetColumn\">\n<p id=\"c040\" class=\"graf graf--p graf-after--figure\">It\u2019s common to run Kali within a virtual environment like\u00a0<a class=\"markup--anchor markup--p-anchor\" href=\"https:\/\/hackernoon.com\/virtualbox-are-you-getting-your-moneys-worth-4d7f98f3d7d2\" target=\"_blank\" rel=\"noopener\" data-href=\"https:\/\/hackernoon.com\/virtualbox-are-you-getting-your-moneys-worth-4d7f98f3d7d2\">VirtualBox<\/a>\u00a0rather than having it take up a whole physical machine. That way you can safely isolate your testing from your regular compute activities\u2026not to mention save yourself significant time and money.<\/p>\n<h4 id=\"4c80\" class=\"graf graf--h4 graf-after--p\">Exploit (penetration) testing<\/h4>\n<p id=\"52fa\" class=\"graf graf--p graf-after--h4\">Here (<strong class=\"markup--strong markup--p-strong\"><em class=\"markup--em markup--p-em\">after<\/em><\/strong>\u00a0obtaining explicit authorization from the organization\u2019s management) is where your pen testers try to actually penetrate your defences to see how far in they can get. Testers will make use of tools like the Metasploit Framework (often also run from Kali Linux), which executes live exploits against target infrastructure. My bad luck: I don\u2019t have a course on Metasploit, but\u00a0<a href=\"http:\/\/pluralsight.pxf.io\/c\/1191769\/424552\/7490?u=pluralsight.com\">other Pluralsight authors<\/a>\u00a0sure do.<\/p>\n<p id=\"e786\" class=\"graf graf--p graf-after--p\">The immediate goal is to leverage any of the network or operating system exploits discovered during the earlier stages of the scanning process. But the ultimate idea, of course, is to shut down the security flaws your pen tester uncovers. All the testing in the world won\u2019t do you an ounce of good if you don\u2019t use it to improve.<\/p>\n<p id=\"6fb8\" class=\"graf graf--p graf-after--p\">Besides the purely technical hacking tools you\u2019ll use, the exploitation phase of pen testing can also incorporate some good old social engineering. That\u2019s where (when authorized) you can use emails, phone calls, and personal contact to try to fool employees into giving up sensitive information.<\/p>\n<p id=\"708c\" class=\"graf graf--p graf-after--p\">It\u2019s a lot of work and requires a great deal of training and preparation to do it well. But if you\u2019re responsible for your company\u2019s IT resources, you can\u2019t leave pen testing for later.<\/p>\n<p id=\"d914\" class=\"graf graf--p graf-after--p\">So what\u2019s your next step? If you\u2019re a do-it-yourself type then by all means, carefully work through some online resources or courseware and dive right in. Otherwise, find a professional you can trust and see what they recommend.<\/p>\n<p id=\"9986\" class=\"graf graf--p graf-after--p\">Good luck!<\/p>\n<p id=\"64ba\" class=\"graf graf--p graf-after--p graf--trailing\"><em class=\"markup--em markup--p-em\">Don\u2019t think I\u2019m just some kind of one-dimensional geek. Besides my\u00a0<\/em><a class=\"markup--anchor markup--p-anchor\" href=\"http:\/\/pluralsight.pxf.io\/c\/1191769\/424552\/7490?subId1=solving&amp;u=https%3A%2F%2Fapp.pluralsight.com%2Fprofile%2Fauthor%2Fdavid-clinton\" target=\"_blank\" rel=\"noopener\" data-href=\"http:\/\/www.shareasale.com\/r.cfm?u=1518299&amp;b=611266&amp;m=53701&amp;afftrack=&amp;urllink=https%3A%2F%2Fapp%2Epluralsight%2Ecom%2Fprofile%2Fauthor%2Fdavid%2Dclinton\"><em class=\"markup--em markup--p-em\">Pluralsight courses<\/em><\/a><em class=\"markup--em markup--p-em\">, I also write\u00a0<\/em><a class=\"markup--anchor markup--p-anchor\" href=\"https:\/\/bootstrap-it.com\/index.php\/books\/\" target=\"_blank\" rel=\"noopener\" data-href=\"https:\/\/bootstrap-it.com\/index.php\/books\/\"><em class=\"markup--em markup--p-em\">books on Linux and AWS<\/em><\/a><em class=\"markup--em markup--p-em\">. Ok. So I suppose I am some kind of one-dimensional geek. This article originally appeared on\u00a0<a href=\"https:\/\/medium.com\/@dbclin\">my Medium account<\/a>.<\/em><\/p>\n<\/div>\n","protected":false},"excerpt":{"rendered":"<p>Got IT infrastructure? Do you know how secure it is? The answer will probably hurt, but this is the kind of bad news you\u2019re better off getting sooner rather than later. The only reasonably sure way to find out what\u2019s&hellip; <a href=\"https:\/\/bootstrap-it.com\/blog\/?p=309\" class=\"more-link\">Continue Reading <span class=\"meta-nav\">&rarr;<\/span><\/a><\/p>\n","protected":false},"author":1,"featured_media":310,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[1],"tags":[],"class_list":["post-309","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-uncategorized"],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v20.2.1 - https:\/\/yoast.com\/wordpress\/plugins\/seo\/ -->\n<title>Penetration testing: choosing the right (Linux) tool stack to fix your broken IT security - Bootstrap IT<\/title>\n<meta name=\"robots\" content=\"index, follow, max-snippet:-1, max-image-preview:large, max-video-preview:-1\" \/>\n<link rel=\"canonical\" href=\"https:\/\/bootstrap-it.com\/blog\/?p=309\" \/>\n<meta property=\"og:locale\" content=\"en_US\" \/>\n<meta property=\"og:type\" content=\"article\" \/>\n<meta property=\"og:title\" content=\"Penetration testing: choosing the right (Linux) tool stack to fix your broken IT security - Bootstrap IT\" \/>\n<meta property=\"og:description\" content=\"Got IT infrastructure? 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Do you know how secure it is? The answer will probably hurt, but this is the kind of bad news you\u2019re better off getting sooner rather than later. 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