Secure your AI, Microsoft 365 and data with confidence.
DigTall Sec delivers focused, expert-led engagements that uncover real risk, prioritize what matters and give your team a clear plan to fix it.
Certified by Microsoft in security
Your engagement is led by a consultant who holds three current Microsoft security certifications, covering architecture, information protection and security operations.
Microsoft Certified: Cybersecurity Architect Expert
SC-100 · Earned Oct 29, 2026
Microsoft Certified: Information Security Administrator Associate
SC-401 · Earned Oct 16, 2026
Microsoft Certified: Security Operations Analyst Associate
SC-200 · Earned Sep 11, 2026
Microsoft and certification names are trademarks of Microsoft Corporation. DigTall Sec is an independent consultancy.
Services
Eight practice areas, each delivered as a fixed-scope engagement with defined deliverables and a clear end date.
AI Security and Readiness
Adopt Microsoft Copilot and other AI tools without exposing sensitive data or creating new attack paths.
- Oversharing and permissions review across SharePoint and OneDrive
- Shadow AI discovery and AI usage policy
- Guardrails, monitoring and governance for AI rollout
AI Application Security
Secure the AI applications, agents and integrations your teams are building.
- Prompt injection and data leakage review
- Agent, plugin and connector permission design
- Secure architecture and threat modeling for LLM apps
Penetration Testing
Controlled, authorized attacks that show how a real adversary would get in and what they could reach.
- External, internal and web application testing
- Microsoft 365, Entra ID and cloud testing
- Evidence-based report with a retest
AI Red Teaming
Adversarial testing of AI assistants, copilots and LLM-based applications.
- Jailbreak and prompt injection testing
- Data exposure and excessive agency checks
- Findings mapped to OWASP guidance for LLM applications
Intune Optimization
Tune device management so every endpoint is compliant, secure and easy to support.
- Compliance, configuration and update policy review
- App deployment and Autopilot improvements
- Security baseline alignment
Enterprise Security Assessment
A structured review of your environment with findings ranked by risk and effort.
- Configuration and posture analysis
- Prioritized findings and quick wins
- Remediation roadmap for your team
Microsoft Purview: Information Protection
Know your data, label it and protect it wherever it goes.
- Classification and sensitivity label design
- Label policies and auto-labeling pilot
- Adoption guidance for end users
Microsoft Purview: DLP
Prevent sensitive data from leaving through email, files and endpoints.
- DLP policy design and tuning
- Pilot in audit mode with real findings
- Alert triage and response process
Identity and Access
Strengthen the layer attackers target first.
- Entra ID and Conditional Access review
- MFA strategy for workforce, partners and customers
- Privileged access and Zero Trust roadmap
Identity is the new perimeter
Most incidents start with a compromised identity or a misconfiguration. We look at how users, devices and data connect in your Microsoft 365 environment and close the gaps attackers actually use.
- Review of sign-in, MFA and Conditional Access posture
- Visibility into guest access and external sharing
- Clear priorities instead of a long list of alerts
How attackers get in today
Four realistic situations we see again and again, and what we do about each one.
A stolen sign-in
A user approves a fake login page. The attacker gets a valid session, reads email and sets up hidden forwarding rules.
- Phishing-resistant MFA and Conditional Access
- Detection of risky sign-ins and mailbox rules
- Tested with a controlled phishing exercise
AI that shows too much
An assistant answers a simple question with content from an HR or finance site that was shared too broadly.
- Permission and oversharing cleanup
- Sensitivity labels and DLP for AI
- Copilot readiness check before rollout
Prompt injection
A document or web page hides instructions that make your AI assistant reveal data or take an action nobody approved.
- Input and output controls
- Least-privilege tools and human approval
- AI red teaming of your assistants
The forgotten exposure
An old server, test app or guest account is reachable from the internet and nobody owns it.
- External attack surface review
- Penetration test with proof of impact
- Ownership, cleanup and retest
AI is moving fast. Security has to keep up.
Copilot, chat assistants, agents and custom AI apps connect to your most sensitive data. We help you adopt them safely, with clear controls and evidence that they work.
Data exposure and oversharing
AI assistants surface whatever users can technically access. We find overshared sites, files and mailboxes before AI makes them easy to discover.
- Permission and sharing analysis
- Sensitivity label coverage
- Prioritized cleanup plan
Shadow AI discovery
Understand which AI tools employees already use and what data goes into them.
- Usage visibility and risk ranking
- Approved and blocked tool lists
- Practical acceptable use policy
AI governance and policy
Rules your teams can follow, mapped to the standards your customers and auditors expect.
- Roles, ownership and approval flow
- Alignment with NIST AI RMF and ISO/IEC 42001
- Risk register for AI use cases
Prompt injection and LLM risks
Attacks that manipulate AI through crafted input, documents or web content.
- Direct and indirect prompt injection review
- Output handling and data leakage checks
- Coverage of the OWASP Top 10 for LLM applications
Agents, plugins and connectors
The more an agent can do, the more it can be abused. We apply least privilege to AI actions.
- Tool and connector permission review
- Human approval for sensitive actions
- Identity and secret handling for agents
Monitoring and response
Know when AI is misused and be ready to respond.
- Audit, DLP and alerting for AI interactions
- Detection use cases and playbooks
- Incident response for AI-related events
What you get
- An AI risk assessment tailored to your environment and use cases
- A prioritized remediation roadmap with quick wins
- Technical guidance for Microsoft 365 Copilot readiness
- Draft AI usage policy and governance model
- Executive summary and technical report for your team
Who it is for
- Teams preparing a Microsoft Copilot rollout
- Security leaders asked to approve AI projects
- Companies building internal AI assistants and agents
- Regulated organizations that need AI controls on paper
Find the weak points before attackers do.
Our penetration tests are authorized, scoped and carefully controlled. You get proof of what is exploitable, why it matters and exactly how to fix it.
External network
Test what an attacker sees from the internet.
- Exposed services and misconfigurations
- Vulnerability validation, not just scanning
- Attack path from perimeter to data
Internal network and Active Directory
Assume an attacker is already inside.
- Privilege escalation and lateral movement
- Active Directory attack paths
- Credential and identity weaknesses
Web applications and APIs
Test the apps your customers and employees depend on.
- Authentication and access control flaws
- Injection and business logic issues
- Aligned with OWASP guidance
Microsoft 365, Entra ID and cloud
Test the identity and cloud layer where most modern attacks land.
- Conditional Access and MFA bypass paths
- Over-privileged apps and service principals
- Azure resource and tenant misconfigurations
Phishing and social engineering
Measure how people and controls respond to realistic lures.
- Controlled phishing simulations
- Email protection and reporting checks
- Awareness findings without blame
Retest and validation
Confirm that fixes actually closed the gap.
- Retest of every reported finding
- Updated status in the final report
- Evidence for auditors and customers
How a penetration test works
Scope and rules
We define targets, timing and rules of engagement, and sign written authorization before any testing.
Discover
Reconnaissance and enumeration to map the real attack surface.
Exploit
Safe, controlled exploitation of validated weaknesses to prove impact.
Report
Clear findings with severity, evidence, business impact and fix guidance.
Retest
We verify remediation and update the report.
What you receive
- Executive summary for leadership
- Technical report with evidence and reproduction steps
- Findings ranked by risk and ease of fix
- Remediation guidance your team can follow
- Walkthrough session and retest
How we keep testing safe
- Written authorization and agreed rules of engagement
- Testing windows that fit your operations
- Immediate contact for critical findings
- Confidential handling of all data and evidence
How we work
Advisory consulting with knowledge transfer. Your team keeps ownership of execution, we make sure it is the right plan.
Scope
A short call to understand goals, environment and success criteria. You get a clear proposal with fixed scope.
Assess
We analyze configuration, policies and data exposure together with your administrators.
Recommend
You receive prioritized findings and a practical plan, ranked by risk and effort.
Enable
We walk your team through the changes so they can run them confidently on their own.
Engagement formats
Choose the format that fits your timeline. Scope and duration are agreed upfront.
Workshop
Hands-on sessions with your team to learn, design and decide.
- Live demos in your tenant or a demo environment
- Design decisions documented
- Slides and recording notes for your team
Assessment
A deep review that ends with findings and a roadmap.
- Structured data collection
- Findings report with priorities
- Executive summary and technical detail
Optimization
Focused tuning of an existing deployment.
- Review of current configuration
- Specific changes recommended step by step
- Knowledge transfer to your admins
Data you can trust
Classify what matters, protect it where it lives and keep compliance simple. Our Purview engagements finish with a pilot your users can already work with.
- Labels people understand and actually use
- DLP that blocks real risk without blocking work
- Governance model your team can maintain
Endpoints under control
From Windows to mobile, we help you manage devices consistently, reduce support effort and raise your security baseline.
- Compliance and conditional access working together
- Cleaner deployment with Autopilot and app packaging
- Fewer exceptions, fewer surprises
About DigTall Sec
DigTall Sec is a boutique consultancy focused on security, identity, endpoints and Microsoft 365. We work with enterprise teams across the Americas and beyond, remotely and in English, with a practical and vendor-aware approach.
Specialized
We do a few things deeply: Microsoft 365 security, identity, endpoints and data protection.
Practical
Every engagement ends with decisions and next steps, not a document that sits on a shelf.
Transparent
Fixed scope, clear deliverables and honest advice, including when a change is not worth the effort.
Frequently asked questions
Quick answers before we talk.
What is AI security?
It is the practice of protecting data, identities and applications when people and systems use AI. It covers data exposure through assistants like Copilot, attacks such as prompt injection, risky agents and plugins, governance and monitoring.
Do you test our own AI applications and agents?
Yes. We review architecture and permissions and run adversarial tests against assistants and LLM-based applications to find prompt injection, data leakage and excessive agency issues.
How is a penetration test different from a vulnerability scan?
A scan lists possible weaknesses automatically. A penetration test is performed by a specialist who validates what can actually be exploited, chains issues together and shows the real business impact.
Will penetration testing disrupt our production systems?
We agree on scope, testing windows and safe methods upfront, avoid destructive actions and keep a direct line open so you can pause testing at any time.
Do you implement the changes for us?
Our work is advisory. We design, review and guide, and your team executes and validates the changes with our support.
Can you work remotely and in our time zone?
Yes. Engagements are delivered remotely in English, and sessions are scheduled to fit your working hours.
How long does an engagement take?
Workshops take one to three days, assessments one to three weeks and optimizations two to four days. We confirm the exact scope and dates in the proposal.
What do we need to provide?
A point of contact, read access to the relevant configuration and a few hours from your administrators. We share a checklist before kickoff.
Is our data safe during the engagement?
We work with the minimum access required, follow your security requirements and can sign an NDA before we start.
How exposed is your company?
Tick every statement that is true today. It takes two minutes and nothing is sent anywhere.
Let's talk about your environment
Tell us what you are trying to protect and we will recommend the right engagement. We reply within one business day.
- Free intro call, no commitment
- Clear proposal with fixed scope
- Email: contact@digtallsec.com