Remote Access & VPN Penetration Testing

First we identify exactly what is exposed: the vendor and model of each gateway, the software version, the authentication methods on offer, and any secondary services the appliance exposes. Version detection matters here because the remote-access space has seen so many critical bugs. An out-of-date Fortinet, Ivanti or Citrix box is often exploitable before login even happens.

Next we pressure the login. We test resistance to credential stuffing using breach data tied to your domains, run controlled password-spray checks that respect lockout thresholds, and probe the MFA implementation for bypasses. Weak second factors, tokens that can be replayed, and portals that reveal valid usernames all get flagged. This is where many real breaches actually begin.

Where a gateway runs a version affected by a known flaw, we verify the exposure safely rather than assuming the version banner tells the truth. The last few years brought pre-authentication vulnerabilities in SSL VPN products from several major vendors, some enabling remote code execution on the appliance itself. We confirm whether yours is genuinely affected, with evidence, and without knocking the device over.

Getting a tunnel is not the end of the story. Once connected, we assess what a compromised remote user can actually reach. A flat network where the VPN drops you next to the domain controllers is a very different risk from one where remote users are boxed into a tightly segmented zone. We test split-tunnel configuration, lateral-movement paths and whether the session can be hijacked or extended.

SSL VPN and gateway appliances are patched far less often than the servers behind them, partly because taking the remote-access edge down disrupts everyone. That lag is exactly what attackers exploit. Pre-authentication path traversal, authentication bypass and remote code execution have all appeared in mainstream products, and unpatched boxes remain live targets long after a fix ships.

Plenty of gateways technically have MFA but implement it in a way that can be sidestepped: a legacy protocol that skips the second factor, an enrollment flow an attacker can hijack, or push notifications vulnerable to fatigue attacks. We test whether your MFA actually stops a valid password from being enough.

The most common configuration failure is not at the perimeter, it is inside. When the tunnel grants broad network access instead of least-privilege routing, one phished VPN credential becomes access to file servers, databases and admin interfaces. We map exactly how far a single account reaches.

Sessions that never re-authenticate, tokens that can be replayed from another location, and portals that leak internal details all extend an attacker’s window. We check the full lifecycle of a remote session, not just the moment of login.

Remote-access portals often reveal more than they should before anyone authenticates: internal hostnames, software build numbers, valid usernames through timing or error differences, and version banners that hand an attacker a precise target list. We flag every pre-authentication leak, because reducing that noise makes your edge meaningfully harder to profile and attack.

Every finding includes a clear impact statement, a CVSS score, the exact steps to reproduce it, and a prioritized fix. Where a known CVE applies, we cite it and confirm your specific exposure rather than relying on a version guess. Screenshots and request captures back up each issue.

Beyond the individual fixes, we give you a hardening path for the remote-access edge: patch priorities, MFA improvements, and segmentation changes that shrink the blast radius of a stolen credential. A free retest confirms the fixes held.

The report is written to satisfy external-testing requirements under the frameworks you work to, so the same engagement that hardens your edge also feeds your compliance file.

ISO 27001:2022 control A.8.20 addresses network security and A.8.21 the security of network services, both directly relevant to remote-access design. For anyone handling cardholder data, PCI DSS 4.0 requirement 11.4 mandates regular penetration testing of the environment, and remote access into the cardholder data environment is squarely in scope.

NIS2 pushes essential and important entities to secure remote access as part of network-security and access-control measures, and a documented VPN penetration test is strong evidence of that. Financial entities under DORA can use the results within their ICT risk-management and resilience testing. We map each finding to the framework you name.

Classic SSL VPN and IPsec setups, whether user-initiated or always-on, remain the backbone for most companies. We test the concentrator, the client authentication, and the routing that decides what a connected device can reach. Always-on designs deserve particular scrutiny because a compromised endpoint is effectively permanently on your network.

Cloud-delivered remote access and vendor-hosted gateways shift some risk to the provider, but not the authentication, the authorization, or the integration with your identity system. We test those layers and the trust you place in the service, since a misconfigured cloud gateway exposes the same internal systems a physical appliance would.

Many organizations are moving from network-level VPN to zero-trust access that brokers each application individually. Done well it shrinks the blast radius considerably. Done partially, it leaves a VPN running alongside it as a soft backdoor. We test both the new broker and any legacy path that undermines it, because attackers target the weakest route in, not the one on your architecture diagram.