How to Set Up Secure Remote Access for Chicago Law Firms

Need to Setup Remote Access for Your Chicago Law Firm? Here’s Our Recommendations 

A managing partner in Chicago recently discovered that three attorneys had been using a personal file-sharing app to send case documents while working from home. No encryption. No audit trail. No way to know who had accessed what, or when. The firm had a VPN – they just didn’t require anyone to use it. That gap is not unusual, and it’s exactly the kind of exposure that leads to a breach, a bar complaint, or both.

Remote work is now standard practice for legal professionals. Attorneys work from home, court waiting rooms, client sites, and airports. That reality creates a real security obligation under ABA Model Rules 1.1 and 1.6, which require law firms to take competent, reasonable measures to protect confidential client information. Setting up secure remote access is not optional, but doing it right requires more than installing a VPN and hoping for the best.

This guide explains what secure remote access actually requires for a Chicago law firm, where the common gaps are, and what a properly structured setup looks like. As a leading provider of IT services for law firms, CTI Technology specializes in helping legal teams access information in a secure manner, regardless of location. 

Why a VPN Alone Is No Longer Sufficient

VPNs have been the standard tool for remote access since the late 1990s, and they still serve a useful purpose. A VPN creates an encrypted tunnel between a remote device and the firm’s internal network, which is a meaningful layer of protection compared to unencrypted connections over public Wi-Fi. However, VPNs were designed for a different threat environment, and relying on one without additional controls creates serious risk.

According to Verizon’s 2025 Data Breach Investigations Report, zero-day exploits targeting edge devices and VPNs grew nearly eightfold in a single year, with 56% of organizations experiencing at least one VPN-related cyberattack. The core problem is architectural: once a user connects through a VPN, they typically gain broad access to the internal network. If that user’s credentials have been stolen, which is how most law firm breaches begin, an attacker inherits that same broad access.

The other problem is behavioral. VPNs are often slow and disruptive to workflows, which means attorneys find workarounds. Personal Dropbox accounts. Personal Gmail. Texting documents to themselves. Each workaround is a security gap that no amount of VPN policy can close if the tool itself creates friction.

A properly structured remote access setup addresses both the technical gap and the usability problem.

The Foundational Layer: Multi-Factor Authentication on Everything

Before any conversation about VPNs, Zero Trust, or endpoint management, the most important security control for a law firm is multi-factor authentication applied consistently across every system that handles client data. Email. Document management systems like iManage and NetDocuments. Practice management platforms. Microsoft 365. Cloud storage. All of it.

MFA is the single most effective control against credential theft, which remains the leading cause of law firm breaches. An attacker who obtains a username and password through phishing still cannot log in if MFA is enforced. The implementation details matter, though. SMS-based MFA is better than nothing but is vulnerable to SIM-swapping attacks. Authenticator apps like Microsoft Authenticator or Duo provide a stronger layer. FIDO2 hardware keys provide the strongest protection for high-privilege accounts like firm administrators and partners with access to trust accounts.

When CTI Technology onboards a new law firm client in the Chicago area, reviewing MFA coverage across cloud services is one of the first assessments completed during the structured kick-off call. Gaps are common. Firms often have MFA enabled for email but not for their document management system, or configured for some users but not for contractors and outside counsel who have access to the same matters. We specialize in cybersecurity solutions, particularly for law firms, so we know the gaps to look for with each and every firm we take on. 

Zero Trust vs. Traditional VPN: What the Difference Means in Practice

Zero Trust Network Access represents a different approach to remote access. Rather than granting a user access to the network and trusting them to stay within appropriate boundaries, ZTNA grants access only to the specific applications or resources a user is authorized to use, and verifies identity and device health continuously during the session.

For a law firm, this distinction is significant. A litigation associate should have access to active case files and the practice management system. They do not need access to the firm’s accounting system or another practice group’s client files. A VPN typically does not enforce that granularity. ZTNA does.

The practical advantages extend beyond security. ZTNA tends to be faster and less disruptive than VPN connections, which increases attorney adoption. It also produces detailed access logs that are useful for demonstrating competent security practices to clients, insurers, and bar associations. Many firms handling sophisticated clients are now being asked to document their security posture before engagement letters are signed – having granular access controls and audit trails supports that conversation.

The shift does not have to happen all at once. A common and practical approach for Chicago law firms in the 25 to 100 attorney range is to implement ZTNA for cloud applications and client portals while maintaining a hardened VPN with MFA and network segmentation for legacy systems and on-premise servers during the transition period.

Endpoint Security: The Device Is Part of the Perimeter

Secure remote access isn’t just about how a user connects. It’s about what device they are connecting from. An attorney working from a personal laptop that has not been updated in six months, has no endpoint detection software, and is shared with family members is a security risk regardless of how strong the firm’s network controls are.

A complete remote access framework for a law firm requires:

1. Endpoint detection and response (EDR) software on every device that accesses firm resources, capable of detecting ransomware and lateral movement in real time
2. Full-disk encryption enabled on all devices, including personal devices used for firm work
3. Mobile device management (MDM) to enforce security policies on smartphones and tablets, with the ability to remotely wipe devices that are lost or stolen
4. Automatic patch management so that operating systems and applications are kept current without depending on individual attorneys to run updates
5. A documented acceptable use policy that defines which devices are permitted to access firm resources and under what conditions

For firms that allow personal devices (BYOD), MDM solutions like Microsoft Intune can separate work data from personal data on the same device, which reduces both security risk and attorney privacy concerns.

What a Complete Secure Remote Access Setup Looks Like for a Chicago Law Firm

Pulling these components together, a properly configured remote access environment for a mid-sized Chicago law firm typically includes:

• MFA enforced across all systems handling client data, with authenticator apps as the standard and hardware keys for privileged accounts
• A VPN with strong encryption and split tunneling disabled, or a ZTNA solution granting least-privilege access to specific applications
• EDR software deployed on all firm-managed endpoints, with real-time monitoring and response capability
• MDM enforcing encryption, screen locks, and remote wipe on all devices, including mobile devices used by attorneys
• Network segmentation that isolates sensitive systems such as trust accounting from general user access
• Access logging and monitoring through Microsoft Conditional Access or equivalent, generating audit trails for every remote session
• A documented remote access policy reviewed annually and updated when the firm’s technology or staffing changes

This is not a one-time setup. Secure remote access requires ongoing management: reviewing access permissions when attorneys join or leave the firm, monitoring for suspicious login patterns, patching VPN appliances and remote access tools as vulnerabilities are discovered, and testing controls against real-world scenarios.

The Onboarding Audit Reveals the Gaps

When CTI Technology begins working with a new law firm client in the Chicago area, the structured kick-off assessment consistently surfaces remote access gaps that the firm didn’t know existed. Attorneys with administrative privileges they no longer need. Cloud service accounts that lack MFA. Former employees whose credentials were never deactivated after departure. Backup systems that have never been tested for recovery.

These are not edge cases. They are standard findings in legal environments where the operational focus is on billable work rather than IT hygiene. The firms that discover these gaps in an onboarding audit are the ones that address them proactively. The firms that discover them after a breach face a much harder path.

For Chicago law firms evaluating their remote access security posture, CTI Technology offers a complimentary assessment that covers network infrastructure, cloud access controls, endpoint protection, and backup and disaster recovery. 

Aaron Kane

CEO of CTI Technology

Aaron Kane is the CEO of CTI Technology, a Chicago-based IT services provider helping businesses navigate technology with confidence. With expertise in IT strategy, infrastructure, cloud solutions, and voice technologies, Aaron focuses on helping organizations improve efficiency, strengthen operations, and make smarter technology decisions. Under his leadership, CTI Technology has continued to grow while maintaining a strong focus on service and long-term client relationships.

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