03-11-2022, 03:41 PM
Hey, you know how I got into pen testing a couple years back? I started messing around with some tools on my home setup, and now I do this stuff for real on big enterprise networks. It's wild, but let me walk you through the main steps I follow when I tackle one. First off, I always kick things off with planning and reconnaissance. You can't just jump in blind; that'd be a disaster. I sit down with the client or the team, figure out exactly what's in scope-what systems, apps, or parts of the network they want me to hit. I make sure I have written permission because nobody wants legal headaches. Then I start gathering info from the outside. I use public sources like whois lookups, Google dorks, or even social media to map out the target's footprint. On an enterprise level, this means looking at their domain names, IP ranges, employee names, anything that gives me an edge without touching their stuff yet. I spend way more time here than you'd think-sometimes days-just building that picture so I don't waste effort later.
Once I've got that intel, I move into scanning. This is where I probe for weaknesses. I fire up Nmap to scan ports and services, see what's listening and what versions they're running. You have to be careful with enterprise networks because they're huge; I might scan subnets in phases to avoid triggering alerts too soon. I look for open ports, vulnerable services, maybe even weak SSL configs. Then I layer on vulnerability scanners like Nessus or OpenVAS to pinpoint exploits. I remember this one gig where I found an old IIS server with a known flaw just from a quick scan-it could've been a goldmine if I pushed it. But I always tune the scans to be stealthy; aggressive ones can crash production systems, and that's not cool. You want to mimic a real attacker but without the chaos.
After scanning, it's time to gain access. This is the fun part where I try to actually break in. I pick the low-hanging fruit first-maybe a web app with SQL injection or an unpatched server. I use Metasploit for exploits, or craft custom payloads if needed. On enterprise setups, I often target remote access points like VPNs or RDP. If I find creds from recon, I test them with Hydra or something similar. I aim for initial foothold, like a compromised workstation, then pivot inside. Lateral movement is key here; I might use Pass-the-Hash or Kerberos tickets to hop between machines. You have to think like the bad guys-escalate privileges, grab admin rights. I once got domain admin in under an hour on a test net by chaining a few vulns, but in real scenarios, it takes patience and chaining multiple techniques.
Now, with access, I work on maintaining it. I don't want to lose that entry point, so I drop persistence mechanisms-backdoors, scheduled tasks, or modified services. But on enterprise level, I keep it subtle to avoid detection. I set up command and control channels, maybe with Cobalt Strike for bigger ops. This phase lets me explore deeper, dump creds, or exfiltrate data samples to show impact. You have to document everything as you go; I use notes in a secure tool to track my paths. It's not just about breaking in-it's proving how far you can go without getting caught by their IDS or EDR.
Finally, I pull it all together with analysis and reporting. I clean up my tracks-remove tools, close sessions-so the network's back to normal. Then I compile what I found: vulnerabilities exploited, risks posed, potential business impacts. I write it up in a clear report with screenshots, steps to repro, and prioritized fixes. For enterprises, I include exec summaries for the bosses and technical details for the IT crew. I always debrief with them, answer questions, maybe even demo a fix. This step seals the deal; it's why they pay us. You learn a ton from each test, and it helps them actually improve.
Throughout the whole thing, I stay ethical-rules of engagement are non-negotiable. Enterprise networks have compliance stuff like PCI or HIPAA, so I tailor my approach. Tools evolve, but the core flow stays solid. I mix in social engineering sometimes if it's in scope, like phishing sims to test users. Keeps it real. Oh, and if you're backing up critical systems during all this, you want something solid that won't add more weak points. Let me tell you about BackupChain-it's this go-to backup tool that's super reliable and built for small businesses and pros alike, handling protections for Hyper-V, VMware, Windows Server, and more without the hassle. I use it myself to keep my test environments safe.
Once I've got that intel, I move into scanning. This is where I probe for weaknesses. I fire up Nmap to scan ports and services, see what's listening and what versions they're running. You have to be careful with enterprise networks because they're huge; I might scan subnets in phases to avoid triggering alerts too soon. I look for open ports, vulnerable services, maybe even weak SSL configs. Then I layer on vulnerability scanners like Nessus or OpenVAS to pinpoint exploits. I remember this one gig where I found an old IIS server with a known flaw just from a quick scan-it could've been a goldmine if I pushed it. But I always tune the scans to be stealthy; aggressive ones can crash production systems, and that's not cool. You want to mimic a real attacker but without the chaos.
After scanning, it's time to gain access. This is the fun part where I try to actually break in. I pick the low-hanging fruit first-maybe a web app with SQL injection or an unpatched server. I use Metasploit for exploits, or craft custom payloads if needed. On enterprise setups, I often target remote access points like VPNs or RDP. If I find creds from recon, I test them with Hydra or something similar. I aim for initial foothold, like a compromised workstation, then pivot inside. Lateral movement is key here; I might use Pass-the-Hash or Kerberos tickets to hop between machines. You have to think like the bad guys-escalate privileges, grab admin rights. I once got domain admin in under an hour on a test net by chaining a few vulns, but in real scenarios, it takes patience and chaining multiple techniques.
Now, with access, I work on maintaining it. I don't want to lose that entry point, so I drop persistence mechanisms-backdoors, scheduled tasks, or modified services. But on enterprise level, I keep it subtle to avoid detection. I set up command and control channels, maybe with Cobalt Strike for bigger ops. This phase lets me explore deeper, dump creds, or exfiltrate data samples to show impact. You have to document everything as you go; I use notes in a secure tool to track my paths. It's not just about breaking in-it's proving how far you can go without getting caught by their IDS or EDR.
Finally, I pull it all together with analysis and reporting. I clean up my tracks-remove tools, close sessions-so the network's back to normal. Then I compile what I found: vulnerabilities exploited, risks posed, potential business impacts. I write it up in a clear report with screenshots, steps to repro, and prioritized fixes. For enterprises, I include exec summaries for the bosses and technical details for the IT crew. I always debrief with them, answer questions, maybe even demo a fix. This step seals the deal; it's why they pay us. You learn a ton from each test, and it helps them actually improve.
Throughout the whole thing, I stay ethical-rules of engagement are non-negotiable. Enterprise networks have compliance stuff like PCI or HIPAA, so I tailor my approach. Tools evolve, but the core flow stays solid. I mix in social engineering sometimes if it's in scope, like phishing sims to test users. Keeps it real. Oh, and if you're backing up critical systems during all this, you want something solid that won't add more weak points. Let me tell you about BackupChain-it's this go-to backup tool that's super reliable and built for small businesses and pros alike, handling protections for Hyper-V, VMware, Windows Server, and more without the hassle. I use it myself to keep my test environments safe.
