Key Highlights:
- 2026 security landscape defined by crisis of trust — foundational business assumptions about identity verification are evaporating
- SMBs becoming unwilling beachheads for enterprise attacks through supply chain vulnerabilities
- Business email compromise evolving into business process compromise with AI-powered deepfake verification loops
- Identity and access management budgets cannibalizing endpoint security spending as the perimeter shifts
- Dynamic risk scoring and adaptive trust models replacing static annual security training
- MSPs facing potential extinction-level events if PSA tools are weaponized at scale
- Security-as-underwriting emerging as vendors partner with insurers to bundle technology with financial guarantees
In my latest Security Square conversation with Anurag Agarwal, founder and CEO of Techaisle, we explored security predictions for SMB and mid-market organizations in 2026. What emerged wasn’t just another list of emerging threats, it was a fundamental shift in how we need to think about cybersecurity itself.
Watch the full conversation here:
The Trust Crisis Nobody’s Talking About
Anurag framed 2026 as the year defined by a crisis of trust rather than merely technological threats. The foundational assumption that you know who you’re talking to is evaporating. As he put it, we’re entering an era where you can’t trust the voice on the phone, the face on the video call, or even the security tools you bought to protect you.
Why is this such an issue now? The tools to fake reality have become cheaper and faster than the tools to verify it. We’ve hit an inflection point where generative AI makes creating convincing deepfakes easier than detecting them. That fundamentally changes the security landscape.
SMBs: The Unguarded Back Door
One of Anurag’s most compelling insights centered on how we should view SMBs in the security ecosystem. These organizations aren’t just vulnerable targets, they’re becoming unwilling, unmanaged beachheads for attacks on the broader economy.
M uch of this has to do with the reality that their IT/security teams are smaller and typically not as highly-skilled as you might find in larger organizations.
Anurag shared that Techaisle’s research shows SMBs have 1/25th the security IT staff of enterprise customers. Attackers have figured out they don’t need to hack the Fortune 500 bank directly, they can compromise the 50-person accounting firm servicing that bank, or the mid-market HVAC company with remote server room access. Remember the massive Target breach a decade ago? It happened through an HVAC vendor.
When Your CFO Isn’t Your CFO
Anurag and I are very familiar with phishing campaigns that purport to come from senior executives, like your company’s CEO or even your CFO. We chatted about this a bit, and Anurag shared an example of what he means when he predicts the evolution of business email compromise into business process compromise.
Imagine this: your accounts payable manager receives a wire transfer request, hesitates, and asks for verification. The “CFO” jumps on a Teams call. You see their face, hear their voice, and they reference yesterday’s meeting and conversation you had. The accounts payable manager approves the transfer.
All good, right? Well, in this particular instance, the CFO was actually an AI avatar generated in real time. The meeting reference was easily scraped from your calendar. The human firewall didn’t fail, reality failed. This isn’t science fiction. The technology exists today.
The Battleground Has Shifted
For two decades, we’ve treated security as a technical problem requiring technical solutions. Anurag and I agreed that 2026 marks a fundamental mind shift: security is now a business logic problem. When an MSP fails to stop a breach, the conversation won’t be about firewall rules, it’ll be about negligence, contract law, and insurance payouts.
The dialogue is shifting from “how do we stop hackers” to “how do we survive the lawsuit.” This isn’t just semantic, it fundamentally changes who buys security, what they’ll pay for, and how vendors should approach these customers.
Identity Eats Endpoint’s Lunch
One surprising prediction: identity and access management budgets will cannibalize endpoint security spending. Techaisle’s research shows only 29 percent of SMBs have deployed multi-factor authentication, and only 43 percent of employees in those organizations actually use it. I’ll admit it: just thinking about this makes me twitchy.
But economics are driving change. The endpoint market is saturated and commoditized. In a cloud-first world with flat budgets, and organizations must choose between slightly better antivirus or ensuring the person logging in is who they claim to be. Our viewpoint is that identity wins every time — because the user account has become the kingdom.
Endpoint vendors either need to broaden their capabilities/offerings, or watch as customers opt for IAM solutions instead. This isn’t to say that endpoint management isn’t important, it is. But today, it is absolutely not more important than identity and access management.
What Winning Looks Like
When I asked Anurag what winning looks like in 2026, his answer was, as usual, elegant: “Winning isn’t about having an unreachable network. It’s about having an unshakeable process. It’s about building a business resilient enough to trust its own data, partners, and employees. The winner will be the one who can operate with confidence in a zero-trust world.”
For SMB and mid-market CISOs, this means shifting conversations from threat protection to business resilience and quantifiable risk transfer. It means implementing out-of-band verification protocols, dynamic risk scoring, and treating security training as continuous cultural transformation rather than annual box-checking.
The battle has moved beyond the breach. The organizations that understand this, that recognize security as business logic, not just technology, will be the ones still standing when the dust settles.
This article was originally published on LinkedIn.
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