Remote access is now the front door to most companies, and VPNs sit squarely on that threshold. The problem is not that VPNs are inherently flawed. The problem is that they are often treated as set-and-forget appliances while everything around them changes: identity systems, devices, cloud apps, compliance rules, attacker techniques. I have spent enough nights troubleshooting VPN outages and incident-response calls to know that strong configuration on day one is not enough. Security is a living discipline, especially at the edge where users, devices, and partners converge.
This article looks at how dedicated Cybersecurity Services, often delivered through Managed IT Services or an MSP Services model, can reduce real risk around remote access VPNs. It blends architecture principles with field notes from deployments and postmortems. The goal is to help you decide where to invest next, and what “good” looks like when VPNs support a hybrid workforce.
The persistent tension: accessibility versus assurance
Security teams want trustworthy authentication, segmentation, and logging. Business leaders want employees, contractors, and vendors to connect from anywhere, on anything, without friction. When that tension isn’t managed deliberately, two things happen. First, administrators make silent compromises: split tunneling enabled without thought, blanket access for “All Users,” and local accounts left in place “for emergencies.” Second, users turn to shadow IT when the VPN feels cumbersome, an even bigger risk.
Cybersecurity Services can focus on reconciling this tension through clear policies and automation. In practice, that means rethinking identity, device posture, and traffic scoping, then instrumenting the entire flow so you can detect drift or abuse.
A quick map of the threat surface
Attackers treat VPN gateways like doorbells on a quiet street: they knock on every one, all day, with stolen credentials, password spray, and opportunistic exploits. What they find varies.
Common issues I have encountered during assessments:
- Excessive trust in a single factor. Static passwords remain widely used, and even where MFA exists, legacy protocols or fallback methods quietly bypass it. Flat networks behind the VPN. Once authenticated, users land on a broad VLAN with reach into file servers, app databases, and even hypervisor consoles. Unmonitored changes. Firmware updates, cipher suites, and policy changes go undocumented. Six months later, everyone has forgotten why IKEv1 is still enabled. Weak logging and telemetry. VPN logs are either not shipped to the SIEM or parsed poorly, so brute force attempts and anomalous geographies blend into noise. Third parties with permanent access. Vendors get persistent accounts because onboarding and offboarding are painful.
Each of these issues can be fixed, but they don’t fix themselves. They demand ownership, repeatable processes, and the right blend of tools. That is where MSP Services or specialized Cybersecurity Services teams add structure and scale.
Identity sits at the center
For remote access, authentication and authorization design carry more weight than the brand of VPN concentrator. If identity is loose, everything beyond it is compensating control.
Multi-factor is table stakes, but details matter. Not all factors carry equal resistance to phishing or adversary-in-the-middle tactics. In the wake of several public breaches, I have seen a noticeable shift from SMS codes and email links to app-based push with number matching or FIDO2 security keys. Where a workforce spans contractors and employees, a mix often works best: FIDO2 for staff on managed devices, modern app push for contractors, and hard tokens for edge cases in air-gapped or high-noise environments.
Conditional access should drive policy at the first handshake. For example, enforce “MFA every time” for sign-ins from countries where you have no business presence, while allowing longer token lifetimes for known devices on expected geographies. Tie policies to risk signals: impossible travel, new device fingerprints, or unfamiliar ASN patterns. Identity providers and modern VPNs can exchange this context, but the plumbing requires hands-on engineering; it does not just appear after a checkbox in the admin console.
A piece of advice from a painful incident: disable legacy protocols completely if your environment allows it. Leaving PAP, MS-CHAPv2, or IKEv1 active only for “old clients” is a common hole. When you cannot remove them yet, aggressively restrict which groups can use them, and monitor those events like smoke alarms.
Device posture and trust but verify
When the pandemic forced companies to connect any laptop at hand, posture checks fell by the wayside. A few years later, many environments still treat all authenticated users as equal, regardless of device state. That is a mistake. I would rather block five legitimate attempts from outdated personal devices than approve one compromised machine into the core network.
Modern remote access should interrogate device posture before and during a session. Antivirus status and disk encryption are the baseline. Stronger posture checks include kernel version for known vulnerabilities, EDR agent presence and health, secure boot status, OS patch level, and whether screen lock and inactivity timers are in place. This isn’t perfect. Posture can be spoofed by determined attackers, but it meaningfully raises the bar and filters out common risks.
For BYOD scenarios, set expectations upfront. If you require an EDR agent or a containerized workspace, say so, and provide a supported path. VDI or browser-isolated workspaces reduce data egress and limit blast radius, especially for contractors. Managed IT Services providers can take the sting out of this by packaging enrollment flows, support scripts, and device profiles that cut onboarding time from days to hours.
Strong cryptography and clean protocol choices
I still see VPNs negotiating old cipher suites because they “just work.” That habit lingers, and it creates leverage for attackers. Choose modern, well-reviewed protocols and ciphers. Phase out IKEv1, DES, 3DES, and weak DH groups. Favor IKEv2 with AES-GCM and modern elliptic curve groups. For TLS-based VPNs, push to TLS 1.2 or 1.3 and prune weak ciphers. If a legacy scanner or appliance breaks, do not weaken the gateway. Segment that legacy system and provide an isolated path.
Certificate hygiene matters too. I have found expired CRLs, long-lived server certificates, and shared private keys between test and production gateways. If your Cybersecurity Services partner offers a PKI health check, take it. Automate certificate lifecycle where possible, and rotate keys on a schedule. A half-day of planned maintenance beats a midnight outage when a certificate quietly dies.
Least privilege through segmentation
The flat network behind a VPN is the fastest way to convert a single compromised account into a company-wide breach. The answer is not blanket denial, it is thoughtful segmentation tied to roles and applications. Users authorized for a finance app do not need SMB access to engineering file shares. Third-party vendors should reach only the servers they maintain, from specific subnets, on specific ports, during defined windows.
Microsegmentation technologies can enforce this at the host or workload level, but even basic steps help. Create access collections mapped to job functions, then test them with real users. You will find odd requirements, like a legacy app that still uses SMB for license checks. Document these exceptions and consider refactoring them rather than loosening global policy.
Split tunneling is another frequent debate. Some security teams forbid it to ensure all traffic routes through inspection points. Others enable it to reduce latency for SaaS. Both stances can be right depending on your controls. If you run robust endpoint protection and you have strong SaaS access policies with inline CASB and DLP, selective split tunneling for trusted destinations can improve user experience without material risk. If you lack those controls, full tunneling makes more sense.
Monitoring that catches trouble early
You cannot defend what you do not see. VPN logs tend to be verbose, inconsistent across vendors, and difficult to parse. Invest in normalization and correlation. At a minimum, capture authentication attempts, success and failure reasons, source IPs and geographies, device identifiers, assigned IPs, and session durations. Bind these to user identities in your SIEM so you can query “show me all activities, VPN through SaaS, for this user in the last 7 days.”
Alerting should reflect behavior, not just counts. A single failed attempt is noise. A slow, even password spray from a single ASN across a dozen accounts is a pattern worth action. Geo-velocity checks and new device detections are low friction wins. For privileged accounts, treat any new location or device as high risk.
Incident-response playbooks need to include VPN-specific steps: force token re-registration, revoke refresh tokens, invalidate VPN sessions, rotate service credentials that might have been captured, and review firewall hits from the user’s assigned IP during the relevant window. During one incident with a vendor account, we found the attacker pivoted to an admin webpage only used once a quarter. The only reason we saw it was a rule that shouted when a VPN IP touched sensitive subnets after-hours.
Managed operations beat heroics
A mature remote access program looks predictable. Certificates renew before they expire. Firmware updates roll out in waves. MFA changes are piloted with a small group and announced in plain language. Entitlements are reviewed quarterly. None of that happens reliably when the VPN is one line item on a long to-do list.
Organizations lean on Managed IT Services and MSP Services to bring rhythm to these tasks. The right partner will schedule maintenance windows, test backups and rollback plans, keep golden configurations under version control, and validate that monitoring actually triggers when policies change. More importantly, they will close the loop between security and operations. If the SOC sees an uptick in SMTP attempts over the VPN, network teams should check if email traffic slipped into an allowed list during a policy tweak.
Contract structure matters. Ask for clear SLAs on response to authentication anomalies, documented change control for policy and firmware updates, and monthly reporting that includes both operational metrics and risk metrics. Measure ticket age for user onboarding and offboarding. I would rather accept a slightly higher monthly cost for a provider that can prove timely offboarding than save a bit and carry dormant accounts for weeks.
Vendor and third-party access
Third parties break the neatness of your identity and device posture. They show up with their own identity providers, laptops, and patch schedules. The instinct is to create local accounts on the VPN and pass them through. Resist that. Negotiate federated access where possible, even if it takes time. If you must create local accounts, keep them behind an approval workflow that includes the sponsor, security, and a defined expiration.
Restrict access windows. If a vendor only needs connectivity on Tuesdays for scheduled maintenance, constrain access to those hours. If their source IP range is predictable, lock it. Use bastion hosts or jump boxes for administrative protocols and record sessions. It sounds heavy-handed until you have to answer regulators about a misstep. It also reduces the operational load when you revoke access, because the scope is already narrow.
Cloud, clientless, and the migration path
Many organizations are moving away from traditional VPNs toward cloud-delivered secure access services. Zero trust network access, reverse proxies, and identity-aware web gateways remove some of the headaches of client distribution and patching. They also enable per-application access rather than broad network connectivity. I have seen success when teams pick a single internal web app with broad use, place it behind an identity-aware proxy, and migrate a pilot group. That early win builds appetite to move more apps and tighten the VPN footprint.
The transition rarely happens in one quarter. Legacy thick clients, printer discovery, and odd protocols keep a VPN around for a while. The trick is to reduce its scope intentionally. Track the share of users and apps still dependent on the VPN each month. Aim for downward progress. Keep pressure on application owners to modernize endpoints or adopt published access patterns. Cybersecurity Services teams can help by mapping dependencies and providing interim controls, like protocol gateways or terminal services.
Compliance without checkbox fatigue
Regulations do not secure systems by IT Services themselves, but they can force helpful habits. For VPNs, common themes appear across frameworks: MFA for remote access, logging and retention, periodic access review, encryption in transit, and vendor management. The temptation is to produce policy documents and call it a day. Auditors eventually ask for evidence. Set up your environment to make evidence easy to collect.
Examples that save time: export monthly lists of active VPN accounts mapped to managers for attestation. Store configuration snapshots and firmware versions with timestamps. Keep a runbook for MFA changes and posture policy updates. Tag SIEM dashboards with control IDs so you can show live status during audits. A good MSP or Managed IT Services provider will include these artifacts by default.
An anecdote: the “temporary exception” that lingered
A mid-sized manufacturer asked for help after a suspicious login. We found a contractor account with broad access and no MFA, created as a “temporary exception” nine months earlier. The contractor left, the account stayed, and attackers eventually found it through password reuse. The VPN logs existed, but were not shipped externally, so correlating activity took hours.
We fixed the immediate problem quickly: disabled the account, rotated sensitive passwords, and forced token re-enrollment for all contractors. The lasting fix took a few weeks. We introduced an expiration policy for all non-employee accounts, enforced by the identity provider and the VPN gateway. We required MFA with number matching on every contractor login, regardless of device. We shipped VPN logs to the SIEM and built a report for accounts nearing expiration. That small set of changes reduced the contractor risk surface dramatically, without adding notable friction to the actual work.
Practical baselines worth enforcing
If your environment needs a crisp starting point, the following baseline reduces most of the predictable risk while keeping operations sane.
- Enforce phishing-resistant MFA for all remote access and block legacy auth protocols. Where FIDO2 is not possible, require app push with number matching and disallow SMS and email. Require device posture checks for corporate devices and use isolated workspaces for BYOD or contractors. Block access when EDR is missing or unhealthy. Segment access by role and application, not just network. Avoid flat networks behind the VPN, and constrain third-party access by time, subnet, and protocol. Maintain modern cryptography: IKEv2, TLS 1.2 or 1.3, strong ciphers, and automated certificate lifecycle. Remove weak suites and legacy handshakes. Centralize logging to a SIEM with user correlation, and alert on behavior signals such as impossible travel, new device, and abnormal after-hours access.
This baseline is achievable in weeks for a focused team or an experienced provider. The refinements that follow will depend on your app portfolio, user mix, and regulatory requirements.
When and how to use an MSP or Cybersecurity Services partner
A strong internal team can run a great VPN program. Many teams, however, juggle too many priorities. Bringing in a partner is not surrendering control, it is buying time and discipline. Choose a partner that treats security and operations as one system. During evaluations, ask them to walk through a real incident they handled, including timelines, evidence, and lessons learned. Request sample runbooks for certificate rotation, firmware upgrades, and MFA migrations. Probe how they handle exceptions, because exceptions become the rule under deadline pressure.
Pricing models vary. Fixed-fee managed services work well when scope is stable and the partner owns outcomes. Time and materials can fit short migrations or complex integrations. Hybrid models appear often: a base fee for steady operations plus project charges for major changes. Insist on clear demarcation of responsibilities. For example, the provider may manage VPN gateways and policy, while your team owns identity and endpoint posture. That clarity reduces finger-pointing during incidents.
Look for providers who speak fluently about identity, not just tunnels. The real work is at the control plane: who you let in, from where, on what terms, into what slices of the environment, and with what level of observability.
Planning for failure, because failure happens
Even with best practices, outages occur. Certificates expire. Cloud identity providers hiccup. Firmware updates misbehave on a subset of appliances. Prepared teams feel different during these moments. They have out-of-band management for administrators, a break-glass access procedure with hardware tokens locked in a safe, and a pre-approved communication plan for users. They roll back confidently because they rehearsed it.
If you have not tested a rollback from a failed VPN upgrade in the last six months, schedule one. If your break-glass accounts have not been used in a year, test them. If your incident runbook is a PDF with no owner, assign one and turn it into a living document. These steps are dull, and they keep companies off breach headlines.
The path forward
Remote access is now a permanent fixture, not a contingency. Traditional VPNs still have a place, especially for legacy protocols and administrative access. They merit the same attention we give identity providers and endpoint protection. The risk is manageable when identity is strong, posture is verified, access is segmented, telemetry is rich, and operations are disciplined.
Cybersecurity Services bring that discipline at scale. Managed IT Services and MSP Services can keep the lights on and the doors locked, while your in-house team focuses on higher-level improvements like replacing thick clients, adopting per-app access, or folding contractor workflows into a unified identity fabric.
If I had to choose a single place to start tomorrow, it would be identity hardening with phishing-resistant MFA and the removal of legacy protocols. It is the hinge on which most of the other controls swing. Right behind it, I would implement posture checks and tighten segmentation for third parties. Do those three things well, then iterate. The result is a remote access environment that is not only safer but also more predictable, easier to audit, and kinder to users who just want to get their work done.