Digital health enters a recalibration phase as ROI pressure reshapes the sector

Digital health is no longer in a build-and-scale mode. Holland & Knight's Healthcare Trend Report, published in mid-2026, characterizes the sector as entering a recalibration phase, one where capital discipline and demonstrable return on investment are replacing earlier growth-first logic. For health system CIOs, operations leaders, and procurement teams, that shift has direct consequences for which vendors survive evaluation and which contracts hold up to scrutiny.

The report, authored by Holland & Knight attorneys including Shannon Britton Hartsfield, covers transactional, regulatory, and litigation developments across the digital health space. The core message for enterprise operators is that the criteria for selecting and contracting with digital health partners are tightening on multiple fronts simultaneously.

AI workflows move from pilot to procurement decision

AI-enabled clinical workflows are a central theme in the report, reflecting a broader market reality: health systems that spent 2024 and 2025 running pilots are now making permanent procurement decisions. The evaluation questions have shifted from capability to performance. Does the tool reduce administrative burden in measurable time units? Does it integrate with existing EHR infrastructure without creating new compliance exposure? Can the vendor document clinical outcome improvements at scale?

Holland & Knight's analysis suggests that these questions are showing up not just in vendor RFPs but in how deals are structured. Performance-linked contract terms, milestone-based payment schedules, and tighter data governance clauses are becoming standard rather than exceptions in digital health agreements.

Chronic disease management draws deal and regulatory attention

The report singles out chronic disease management as another high-focus area, which aligns with where health systems see the largest long-term cost exposure. Remote monitoring platforms, AI-assisted care protocols, and population health tools targeting conditions like diabetes, heart disease, and hypertension are drawing both deal flow and regulatory attention. That dual spotlight matters operationally: a vendor that looks strong commercially may carry meaningful regulatory or reimbursement risk that only surfaces after contract signing.

For procurement teams, Holland & Knight's framing is a practical signal to run parallel tracks when evaluating these vendors. Legal review of compliance posture should happen at the same time as clinical and financial due diligence, not after a preferred vendor is already selected.

Three risk dimensions converge on digital health contracts

One of the more operationally pointed observations in the report is that transactional, regulatory, and litigation trends are all moving at once. Health systems that approach digital health contracting through a single lens, focusing only on price or only on compliance, are likely to miss exposure in one of the other two dimensions. Regulatory guidance on AI in clinical settings is still developing, which means contracts executed today may need amendment windows built in. Litigation patterns around data privacy and AI-generated clinical recommendations are also shifting, adding liability considerations that were not standard in digital health agreements just two years ago.

The practical implication for enterprise teams is structural: digital health vendor reviews in 2026 require input from legal, IT, clinical leadership, and finance before a deal moves to signature, not as a formality but as a risk-management necessity.

What this means for your team

• Rebuild your vendor scorecard. Add explicit ROI documentation requirements to any digital health RFP, including baseline metrics, measurement methodology, and a defined review period. Vendors who cannot answer these questions at the proposal stage carry higher post-implementation risk.
• Run a three-track due diligence process for any chronic disease management or AI workflow platform: clinical outcomes evidence, current regulatory posture, and litigation or enforcement history. Sequence them in parallel, not sequentially.
• Build contract flexibility into AI clinical workflow agreements now. Include amendment triggers tied to regulatory guidance changes, and define data governance obligations with specificity, particularly around model outputs used in clinical decision support.
• Align procurement timelines with your legal team's bandwidth. The convergence of transactional, regulatory, and litigation complexity in digital health means compressed review cycles create real exposure. Factor that into project schedules.