Redefining HIPAA Compliance with AI-Powered Assurance

By George Totev, Chief Information Security Officer at Trustero

Our company is traveling to the HIMSS ‘25 conference in Las Vegas next week and it got me thinking about how a GRC AI Assistant can be applied to healthcare organizations, specifically achieving and maintaining HIPAA compliance. If you already have a HIPAA compliance program I would love to hear from you.

Ensuring compliance with regulations like HIPAA could be quite challenging. The complexity for Providers could be quite daunting; for Business Associates it is yet another framework and a set of requirements to maintain. The self-attestation nature brings an additional twist to HIPAA compliance.?

Let’s examine how a GRC AI Assistant like Trustero could help in this case, with a focus on two specific areas:

• Continuous control monitoring and assurance; and
• Collaboration with other stakeholders, including the Legal Department

AI-Driven Compliance Assurance: The Next Generation of GRC

For everyone who has been in compliance for a while there are two very stressful moments:

• Audit readiness. We all know that the more thorough audit preparation is, the less painful the audit will be. A good practice is to verify all the controls, review the corresponding policies, procedures and standards, sample and review the evidence. The old adage “More sweat in training; less blood in battle” applies here. However, very often the sweat turns into “blood and tears” - chasing people around the organization for the correct and thorough evidence; something somewhere changed and the control is not working anymore; a new use case changed the risk profile of an existing vendor and we have just found out about it, etc.
• The audit itself. Especially with more complicated audits the evidence may be there but not exactly correct, from the correct system, have the correct date/period, etc. The auditors will have follow up questions, need for additional clarifications, etc.

We all know one of the better solutions to those problems - continuous controls monitoring and assurance. Being notified in (almost) real time when the policy-control-control evidence change is broken, potentially with some recommendations on how to fix it, will not only significantly reduce the stress but also increase the assurance in our risk management system. People who manage compliance frameworks (e.g. FedRAMP) which include continuous monitoring, will attest to the benefits of such a system.

Unfortunately, they will also attest to the enormous efforts necessary to maintain such a system. That is why a lot of us endure the stress of point in time “audit periods” instead of enjoying the bliss of continuous monitoring.

A GRC AI Assistant, like Trustero, sits on top of your existing GRC solution, has access to the necessary data, and could tip the balance in favor of the bliss state. It allows you not only to continuously check the policy-control-evidence chain but also does a contextual check of the evidence itself. For example, uploading the result of a DR test is not sufficient the agent will actually check if the test met the RTO/RPO requirements. Such automation enables organizations to:

• Streamline audit readiness – Automate evidence collection and validation to reduce time spent on reviewing documentation.
• Proactively identify compliance gaps – Leverage AI to detect misalignments before they become audit issues.
• Ensure control effectiveness – Continuously monitor controls to validate their real-world implementation.

Trustero seamlessly integrates with existing security and compliance ecosystems, including GRC platforms and document management systems like Google Drive and SharePoint, making it easy to ingest, analyze, and act on compliance data.

Let’s dive a little deeper and see how a GRC AI Assistant could help with onboarding and maintaining HIPAA attestation.

HIPAA Attestation: A Smarter, More Efficient Approach

For organizations seeking HIPAA attestation, the path can vary. Some opt for frameworks like HITRUST, while others integrate HIPAA-specific controls into SOC 2. Regardless of the approach, first we have to identify the gaps and create an implementation plan.

Traditionally, that will include a few experts and a few months of sifting through policies, procedures, standards, controls, etc., number of meetings not only with GRC but also other teams across the organization.?

With AI GRC Assistant we can use a questionnaire that is based on the HIPAA regulatory requirements and match it against our existing environment. The GRC AI Assistant already has access to the existing GRC system, document repositories with various supporting documents, control evidence, architectural diagrams, certificates, etc. All of that is used as the context to answer the HIPAA? questionnaire - not much different than answering a vendor questionnaire. We do not eliminate the expert - someone needs to verify the answers and recommendations - but we significantly shorten the analysis: from months to days.

Based on the gap assessment and the plan we implement the controls. Now, it is time to make sure that they:

• Align with the policies (design effectiveness)
• They are properly implemented
• Correct evidence is gathered and it supports the control (operational effectiveness)

GRC AI Assistant like Trustero can perform those checks as part of the implementation (monitoring progress) and continuously thereafter (continuous monitoring and assurance). Consider this three level check for a common HIPAA requirement—data backup and disaster recovery:

• Verifies compliance documentation – AI automatically checks for backup test records and retention policies.
• Validates adherence to RTO and RPO objectives – Ensures that recovery time objectives (RTO) and recovery point objectives (RPO) are met.
• Detects potential compliance gaps – Identifies missing documentation or inconsistencies in control implementation.

This level of automation dramatically reduces the manual burden on compliance teams while increasing confidence in audit readiness.

AI-Powered Compliance Insights for Legal and Risk Teams

Now that we have implemented HITRUST, SOC2+, or something else, ensured that our controls are working and proper evidence is collected, potentially achieved successful audit, inevitably Legal will come to us with the familiar “Are we really ready to attest compliance?”. It is usually followed by a number of very pointed, detailed questions. We have been through those considerations, auditors most likely checked them but we still need days (or maybe weeks) to confirm the data and formulate the answer. Unsurprisingly, Internal Audit also has similar questions.

Traditionally, the person who runs the HIPAA program will probably repeat some of the steps already performed during preparation and audit to engage with the correct stakeholders, collect, confirm and curate the information so that they can provide the answers. It is very likely that it will be an iterative process - answers will generate more questions and clarifications.

AI GRC Assistant, like Trustero, already has access to all that information. We can use the same questionnaire tool to interrogate the system and receive the answers in a matter of minutes, not weeks. In fact, we will even receive explanations and reasoning behind every answer so that we can quickly evaluate it. Such AI-driven compliance Q&A capability enables teams to:

• Ask compliance-related questions in natural language – No need to manually comb through scores of various documents.
• Receive instant, data-backed answers – AI pulls relevant evidence and generates actionable insights.
• Proactively mitigate risk – Identify potential exposure before it leads to a compliance failure.

By replacing manual research with real-time AI-driven insights, AI GRC Assistants like Trustero empower organizations to take a proactive approach to compliance. Q&A AI agent becomes an invaluable tool for effective risk management. It can help not only with evaluation of the current posture but also with assessing various “What If?” scenarios that we often create as part of the gap assessment process.

Moving Beyond Check-the-Box Compliance

HIPAA compliance should not be a burdensome, reactive exercise—it should be an ongoing, intelligent process that strengthens security and risk management. AI GRC Assistant like Trustero enables organizations to:

• Turn compliance into a business advantage – Demonstrate security maturity to customers, partners, and regulators.
• Automate compliance operations – Reduce inefficiencies and free up resources for higher-value security initiatives.
• Ensure real-time control validation – Move beyond point-in-time audits with continuous compliance monitoring.

What do you think?

If you already have a HIPAA Compliance program I would love to hear from you. What is the biggest challenge you face? I have been on the BA side but only heard of the Provider side - what are your specific concerns? Do you use any generic or specialized AI tools to support your compliance program? What challenges do you see with AI in compliance and security?

And if you are coming to HIMSS ‘25 in Las Vegas - please stop by our booth.

See Trustero in action—visit trustero.com to learn more.