Top IT Challenges Businesses Faced in 2025 and How to Overcome Them in 2026

As technology advances, so do the challenges businesses face in keeping their IT environments secure, efficient and resilient. In 2025, organizations grappled with everything from phishing attacks and hijacked MFA tokens to outdated infrastructure and the growing threat of AI-driven cybercrime. These issues didn’t just create headaches—they put data, operations and reputations at risk.

The good news? With proactive planning and the right strategies, you can avoid these pitfalls in 2026. Below, we break down the most common IT challenges businesses faced last year and share practical ways to overcome them—plus how Elevity can help you stay ahead.

• Phishing Attempts Continue to Target Businesses
• Hijacked Multifactor Authentication Tokens Pose a Growing Risk
• Difficulty Determining the Right Frequency for Employee Cybersecurity Education
• Legacy Systems Blocking Digital Transformation
• Lack of Disaster Recovery Plans

Ready to learn more? Let’s dive in.

Phishing Attempts Continue to Target Businesses

Phishing remains one of the most common—and costly—cybersecurity threats. These attacks trick employees into revealing sensitive information or clicking malicious links, often leading to data breaches or financial loss. The challenge is that phishing tactics evolve constantly, making it harder for businesses to stay ahead. Regular employee training, simulated phishing tests and strong email security measures are essential to reduce risk.

Elevity helps businesses fight phishing with a layered approach. We can provide ongoing security awareness training, realistic phishing simulations and advanced email filtering tools to help catch threats before they reach your inbox. Our team also stays on top of emerging phishing trends, so your employees are prepared to spot and stop attacks before they cause harm.

Hijacked Multifactor Authentication Tokens Pose a Growing Risk

Multifactor authentication (MFA) is designed to strengthen security, but attackers are finding ways to exploit it. Token theft—often triggered by malicious email attachments—can give hackers unauthorized access even when MFA is enabled. Signs of compromise include suspicious login activity, unexpected MFA prompts and altered Outlook mailbox rules. Cybercriminals are using AI-driven tactics to bypass detection, so businesses must stay vigilant and educate employees to spot red flags like unusual SharePoint invitations.

Elevity can help protect your organization from MFA hijacking with advanced monitoring, AI-driven threat detection and proactive security measures. We implement best practices like phishing-resistant MFA, continuous login activity reviews and mailbox rule audits. Our team provides guidelines to better ensure that your authentication systems remain secure, so attackers can’t turn your defenses into vulnerabilities.

Difficulty Determining the Right Frequency for Employee Cybersecurity Education

Businesses often ask: What’s the best way—and cadence—to train employees on cybersecurity? It’s a fair question because human error remains the leading cause of data breaches. Even the most advanced security tools can’t protect your organization if employees unknowingly click on a phishing link or use weak passwords.

General Best Practices

• Frequency: Cybersecurity awareness training shouldn’t be a “one and done” event. Industry experts recommend at least quarterly refreshers, with shorter monthly touchpoints for high-risk roles.
• Format: Mix things up—combine interactive modules, phishing simulations and quick video tips to keep engagement high.
• Relevance: Tailor content to real-world threats employees face daily, like phishing emails, social engineering and safe remote work practices.

Regular training builds a culture of security, making employees your first line of defense rather than your weakest link.

Elevity takes the guesswork out of cybersecurity training by creating programs tailored to your industry and risk profile. We provide ongoing reinforcement through phishing simulations and bite-sized learning modules, ensuring employees stay engaged and informed. Plus, our experts are always monitoring emerging threats. They will offer insightful suggestions about how to best update your training, so your team is always prepared to defend against the latest attacks.

Legacy Systems Blocking Digital Transformation

Outdated infrastructure is one of the biggest obstacles to modernization. Many businesses—especially small and mid-sized organizations—delay upgrades due to cost concerns or resistance to change. Unfortunately, legacy systems often slow down operations, limit integration with new technologies and increase security risks. Without timely updates, businesses struggle to stay competitive and agile in a rapidly evolving digital landscape.

Elevity partners with businesses to create phased modernization plans that minimize disruption and control costs. We help identify critical systems to upgrade first, implement scalable cloud solutions and ensure smooth integration with new technologies. With Elevity’s guidance, your digital transformation becomes achievable and sustainable.

Lack of Disaster Recovery Plans

When disaster strikes—whether it’s a cyberattack, hardware failure, or natural event—businesses without a disaster recovery plan risk major operational disruptions, damaged reputations and lost customers. A well-designed plan ensures your systems and data can be restored quickly, minimizing downtime and financial impact. Don’t wait until it’s too late; proactive planning is essential for resilience.

Elevity works with businesses to create customized disaster recovery strategies that fit their unique needs. From secure backups to tested recovery protocols, we make sure your organization is prepared for the unexpected. With our expertise, you can protect your operations and maintain customer trust—even when challenges arise.

Preparing for AI-Driven Cybersecurity Threats

As cybercriminals adopt artificial intelligence (AI) to launch more sophisticated attacks, businesses face a new IT challenge: staying one step ahead. AI-powered threats can bypass traditional defenses, automate phishing campaigns and exploit vulnerabilities faster than ever. To counter this, organizations need advanced planning and tools that can analyze massive amounts of network data in real time. Security Information and Event Management (SIEM) solutions are critical—they quickly identify anomalies that could signal an attack and help teams respond before damage occurs.

Elevity equips businesses with proactive strategies to defend against AI-driven threats. We implement SIEM solutions, monitor suspicious activity and leverage AI-based detection tools to keep your systems secure. With Elevity, you gain the expertise and technology needed to outsmart evolving cybercriminal tactics.

The IT challenges businesses faced in 2025—from phishing attacks to legacy systems and AI-driven threats—underscore one truth: technology isn’t slowing down and neither are cybercriminals.

Preparing for 2026 means taking proactive steps now—strengthening security, modernizing infrastructure and building resilience against evolving risks. With the right strategy and a trusted partner like Elevity, your business can stay secure, agile and ready for what’s next.

Want to empower your team to be your first line of defense? Download our free infographic, Cybersecurity Tips for Employees, and share it with your staff today.