Preventing Data Leakage to AI: A Strategic Framework for the Global Enterprise
In an organization with thousands of users, "Shadow AI" isn't just an IT nuisance - it’s a fundamental shift in the risk surface. We’ve all seen it: a well-intentioned employee pastes proprietary code into a public LLM to "clean it up," or a team lead uploads a customer list to a "free" AI formatter. These aren't malicious acts; they are productivity shortcuts that create massive security gaps. To enable innovation without compromising safety, we need a Zero Trust–aligned framework that acts as a guardrail rather than a gate. This requires a layered model centered on Identity, Device Health, and Data Intelligence. The 7-Layer Defense Architecture In a complex tenant, we don't rely on a single gatekeeper. We implement a stack where each layer provides a fail-safe for the one before it. Layer Enterprise Objective Primary Technology 1. Identity Anchor Verified Access & Device Health Microsoft Entra ID + Intune 2. Global Radar Continuous Shadow AI Discovery Purview AI Hub + Defender for Cloud Apps 3. Session Guard Real-time Intervention & Input Filtering Conditional Access App Control (MCAS) 4. Data Core Auto-Labeling & Persistent DLP Microsoft Purview Information Protection 5. Agent Governance Lifecycle & Identity for AI Agents Agent 365 + Entra Agent ID 6. The Human Layer Secure Prompting & AI Skilling Approved Prompt Templates & Training 7. Continuous Ops Monitoring & Regulatory Auditability Microsoft Sentinel + Insider Risk Mgmt 1. Universal Discovery via the Purview AI Hub Visibility is the prerequisite for governance. In a complex environment, you need a "single pane of glass" to monitor AI usage across the tenant. The Insight: Use the Purview AI Hub to identify "high-risk" prompts and see exactly which sensitive data types (PII, IP, Code) are being shared. The Radar: Integration with Defender for Endpoint ensures we capture AI usage even when users are off-network or traveling, leaving no blind spots in the global telemetry. 2. Identity-Driven Access & Tenant Boundaries Access must be tied to the health of the device. If the device isn't managed, the AI shouldn't be reachable. Conditional Access: Enforce policies requiring a "Managed and Compliant" device for any AI service. The "Account Leak" Fix: Deploy Tenant Restrictions v2 (TRv2). This is the only way to effectively stop employees from using corporate assets to sign into personal Microsoft accounts, keeping data strictly within your managed boundary. 3. Real-Time Session Governance & Inbound Protection The biggest leak in the enterprise isn't a hack; it's the copy-paste. However, we must also guard against Prompt Injection. Granular Controls: Use Session Policies to allow an AI tool while blocking specific risky actions - like uploading a document with a "Highly Confidential" label. Inbound Sanitization: Implement filters to detect malicious external data that might attempt to "hijack" a session via Indirect Prompt Injection. Continuous Access Evaluation (CAE): This ensures that if a user’s risk level changes, their access to AI is revoked in near real-time. 4. Hardening the Data (Auto-Classification & DLP) If security is embedded in the data, the location of the data becomes secondary. Intelligent Labeling: Move beyond manual tagging. Use Auto-labeling at the service level to scan and encrypt sensitive data (e.g., credit card numbers or internal project names) before it can be processed by an LLM. Clipboard Guard: Use Endpoint DLP to stop the "Clipboard Leak." This prevents users from moving sensitive text from a protected document into a web-based AI interface. 5. The "Agentic" Era: Agent 365 As we move from chatbots to autonomous agents, governance must manage an ecosystem of AI agents. Agent 365: A centralized control plane to manage the registry and lifecycle of every AI agent (sanctioned or "shadow") active in your tenant. Entra Agent ID: Treat agents like enterprise identities. Assign unique IDs to manage permissions so an agent’s access doesn't outlive its business purpose. 6. The Human Layer: Skilling & Secure Prompting Technical guardrails are the safety net, but user intent is the driver. Context Minimization: Train users to provide AI with only the data it needs. Redacting proprietary names or PII before prompting should be a baseline habit. The "Safe Harbor": Move users away from risky public tools by providing a superior experience in Microsoft 365 Copilot. Security shouldn't be a "No," it should be a "Yes, use this instead." 7. Continuous Ops & Regulatory Compliance Security is not a "set and forget" project. For the global enterprise, this layer provides the Audit Trail required for the EU AI Act and GDPR. Shadow AI Migration: Track the % of users moving from "Shadow" to sanctioned tools. Sentinel Correlation: Correlate AI prompts and DLP alerts in Microsoft Sentinel to allow the SOC to automate responses to misuse. Compliance Reporting: Generate automated reports on data residency and AI interaction logs to satisfy global regulatory requirements. Technical & Licensing Baseline This framework focuses on identity-, data-, and app/session-level controls (e.g., Defender for Cloud Apps/CAAC). It does not include network-level controls such as Cloud Proxy or ZTNA, which can complement these measures. Most capabilities require Microsoft 365 E5 and Entra ID P2. Features like Purview AI Hub, Agent 365, and Entra Agent ID may be in preview or offered as add-ons - verify availability and licensing with your Microsoft account team. Conclusion Securing AI at scale is not about building a wall; it is about engineering a dynamic foundation. In a global enterprise, "No" is a temporary delay, not a sustainable policy. By anchoring our strategy in Identity, Auto-Classification, and Agentic Governance, we transform AI from a fragmented "shadow risk" into a governed, competitive advantage. This framework ensures that as our digital ecosystem evolves, the organization's "crown jewels" remain protected - not by restricting innovation, but by making security the adaptive, automated engine that powers it.Step by Step: 2-Tier PKI Lab
Purpose of this blog Public Key Infrastructure (PKI) is the backbone of secure digital identity management, enabling encryption, digital signatures, and certificate-based authentication. However, neither setting up a PKI nor management of certificates is something most IT pros do on a regular basis and given the complexity and vastness of the subject it only makes sense to revisit the topic from time to time. What I have found works best for me is to just set up a lab and get my hands dirty with the topic that I want to revisit. One such topic that I keep coming back to is PKI - be it for creating certificate templates, enrolling clients, or flat out creating a new PKI itself. But every time I start deploying a lab or start planning a PKI setup, I end up spending too much time sifting through the documentations and trying to figure out why my issuing certificate authority won't come online! To make my life easier I decided to create a cheatsheet to deploy a simple but secure 2-tier PKI lab based on industry best practices that I thought would be beneficial for others like me, so I decided to polish it and make it into a blog. This blog walks through deploying a two-tier PKI hierarchy using Active Directory Certificate Services (AD CS) on Windows Server: an offline Root Certification Authority (Root CA) and an online Issuing Certification Authority (Issuing CA). We’ll cover step-by-step deployment and best practices for securing the root CA, conducting key ceremonies, and maintaining Certificate Revocation Lists (CRLs). Overview: Two-Tier PKI Architecture and Components In a two-tier PKI, the Root CA sits at the top of the trust hierarchy and issues a certificate only to the subordinate Issuing CA. The Root CA is kept offline (disconnected from networks) to protect its private key and is typically a standalone CA (not domain-joined). The Issuing CA (sometimes called a subordinate or intermediate CA) is kept online to issue certificates to end-entities (users, computers, services) and is usually an enterprise CA integrated with Active Directory for automation and certificate template support. Key components: Offline Root CA: A standalone CA, often on a workgroup server, powered on only when necessary (initial setup, subordinate CA certificate signing, or periodic CRL publishing). By staying offline, it is insulated from network threats. Its self-signed certificate serves as the trust anchor for the entire PKI. The Root CA’s private key must be rigorously protected (ideally by a Hardware Security Module) because if the root is compromised, all certificates in the hierarchy are compromised. Online Issuing CA: An enterprise subordinate CA (domain-joined) that handles day-to-day certificate issuance for the organization. It trusts the Root CA (via the root’s certificate) and is the one actually responding to certificate requests. Being online, it must also be secured, but its key is kept online for operations. Typically, the Issuing CA publishes certificates and CRLs to Active Directory and/or HTTP locations for clients to download. The following diagram shows the simplified view of this implementations: The table below summarizes the roles and differences: Aspect Offline Root CA Online Issuing CA Role Standalone Root CA (workgroup) Enterprise Subordinate CA (domain member) Network Connectivity Kept offline (powered off or disconnected when not issuing) Online (running continuously to serve requests) Usage Signs only one certificate (the subordinate CA’s cert) and CRLs Issues end-entity certificates (users, computers, services) Active Directory Not a member of AD domain; doesn’t use templates or auto-enrollment Integrated with AD DS; uses certificate templates for streamlined issuance Security Extremely high: physically secured, limited access, often protected by HSM Very High: server hardened, but accessible on network; HSM recommended for private key CRL Publication Manual. Admin must periodically connect, generate, and distribute CRL. Delta CRLs usually disabled. Automatic. Publishes CRLs to configured CDP locations (AD DS, HTTP) at scheduled intervals. Validity Period Longer (e.g. 5-10+ years for the CA certificate) to reduce frequency of renewal. Shorter (e.g. 2 years) to align with organizational policy; renewed under the root when needed. In this lab setup, we will create a Contoso Root CA (offline) and a Contoso Issuing CA (online) as an example. This mirrors real-world best practices which is to "deploy a standalone offline root CA and an online enterprise subordinate CA”. Deploying the Offline Root CA Setting up the offline Root CA involves preparing a dedicated server, installing AD CS, configuring it as a root CA, and then securing it. We’ll also configure certificate CDP/AIA (CRL Distribution Point and Authority Information Access) locations so that issued certificates will point clients to the correct locations to fetch the CA’s certificate and revocation list. Step 1: Prepare the Root CA Server (Offline) Provision an isolated server: Install a Windows Server OS (e.g., Windows Server 2022) on the machine designated to be the Root CA. Preferably on a portable enterprise grade physical server that can be stored in a safe. Do not join this server to any domain – it should function in a Workgroup to remain independent of your AD forest. System configuration: Give the server a descriptive name (e.g., ROOTCA) and assign a static IP (even though it will be offline, a static IP helps when connecting it temporarily for management). Install the latest updates and security patches while it’s still able to go online. Lock down network access: Once setup is complete, disable or unplug network connections. If the server must remain powered on for any reason, ensure all unnecessary services/ports are disabled to minimize exposure. In practice, you will keep this server shut down or physically disconnected except when performing CA maintenance. Step 2: Install the AD CS Role on the Root CA Add the Certification Authority role: On the Root CA server, open Server Manager and add the Active Directory Certificate Services role. During the wizard, select the Certification Authority role service (no need for web enrollment or others on the root). Proceed through the wizard and complete the installation. You can also install the CA role and management tools via PowerShell: Install-WindowsFeature AD-Certificate -IncludeManagementToolsThis Role Services: Choose Certification Authority. Setup Type: Select Standalone CA (since this root CA is not domain-joined). CA Type: Select Root CA. Private Key: Choose “Create a new private key.” Cryptography: If using an HSM, select the HSM’s Cryptographic Service Provider (CSP) here; otherwise use default. Choose a strong key length (e.g., 2048 or 4096 bits) and a secure hash algorithm (SHA-256 or higher). CA Name: Provide a common name for the CA (e.g., “Contoso Root CA”). This name will appear in issued certificates as the Issuer. Avoid using a machine DNS name here for security – pick a name without revealing the server’s actual hostname. Validity Period: Set a long validity (e.g., 10 years) for the root CA’s self-signed certificate. A decade is common for enterprise roots, reducing how often you must touch the offline CA for renewal. Database: Specify locations for the CA database and logs (the defaults are fine for a lab). Review settings and complete the configuration. This process will generate the root CA’s key pair and self-signed certificate, establishing the Root CA.Post-install configuration: After the binary installation, click Configure Active Directory Certificate Services (a notification in Server Manager). In the configuration wizard: You can also perform this configuration via PowerShell in one line: Install-AdcsCertificationAuthority ` -CAType StandaloneRootCA ` -CryptoProviderName "YourHSMProvider" ` -HashAlgorithmName SHA256 -KeyLength 2048 ` -CACommonName "Contoso Root CA" ` -ValidityPeriod Years -ValidityPeriodUnits 10 This would set up a standalone Root CA named "Contoso Root CA" with a 2048-bit key on an HSM provider, valid for 10 years. Step 3: Integrate an HSM (Optional but Recommended) If your lab has a Hardware Security Module, use it to secure the Root CA’s keys. Using an HSM provides a dedicated, tamper-resistant storage for CA private keys and can further protect against key compromise. To integrate: Install the HSM vendor’s software and drivers on the Root CA server. Initialize the HSM and create a security world or partition as per the vendor instructions. Before or during the CA configuration (Step 2 above), ensure the HSM is ready to generate/store the key. When running the AD CS configuration, select the HSM’s CSP/KSP for the cryptographic provider so that the CA’s private key is generated on the HSM. Secure any HSM admin tokens or smartcards. For a root CA, you might employ M of N key splits – requiring multiple key custodians to collaborate to activate the HSM or key – as part of the key ceremony (discussed later). (If an HSM is not available, the root key will be stored on the server’s disk. At minimum, protect it with a strong admin passphrase when prompted, and consider enabling the option to require administrator interaction (e.g., a password) whenever the key is accessed.) Step 4: Configure CA Extensions (CDP/AIA) It’s critical to configure how the Root CA publishes its certificate and revocation list, since the root is offline and cannot use Active Directory auto-publishing. Open the Certification Authority management console (certsrv.msc), right-click the CA name > Properties, and go to the Extensions tab. We will set the CRL Distribution Points (CDP) and Authority Information Access (AIA) URLs: CRL Distribution Point (CDP): This is where certificates will tell clients to fetch the CRL for the Root CA. By default, a standalone CA might have a file:// path or no HTTP URL. Click Add and specify an HTTP URL that will be accessible to all network clients, such as: http://<IssuingCA_Server>/CertEnroll/<CaName><CRLNameSuffix><DeltaCRLAllowed>.crl For example, if your issuing CA’s server name is ISSUINGCA.contoso.local, the URL might be http://issuingca.contoso.local/CertEnroll/Contoso%20Root%20CA.crl This assumes the Issuing CA (or another web server) will host the Root CA’s CRL in the CertEnroll directory. Check the boxes for “Include in the CDP extension of issued certificates” and “Include in all CRLs. Clients use this to find Delta CRLs” (you can uncheck the delta CRL publication on the root, as we won’t use delta CRLs on an offline root). Since the root CA won’t often revoke its single issued cert (the subordinate CA), delta CRLs aren’t necessary. Note: If your Active Directory is in use and you want to publish the Root CA’s CRL to AD, you can also add an ldap:///CN=... path and check “Publish in Active Directory”. However, publishing to AD from an offline CA must be done manually using the following command when the root is temporarily connected. certutil -dspublish Many setups skip LDAP for offline roots and rely on HTTP distribution. Authority Information Access (AIA): This is where the Root CA’s certificate will be published for clients to download (to build certificate chains). Add an HTTP URL similarly, for example: http://<IssuingCA_Server>/CertEnroll/<ServerDNSName>_<CaName><CertificateName>.crt This would point to a copy of the Root CA’s certificate that will be hosted on the issuing CA web server. Check “Include in the AIA extension of issued certificates”. This way, any certificate signed by the Root CA (like your subordinate CA’s cert) contains a URL where clients can fetch the Root CA’s cert if they don’t already have it. After adding these, remove any default entries that are not applicable (e.g., LDAP if the root isn’t going to publish to AD, or file paths that won’t be used by clients). These settings ensure that certificates issued by the Root CA (in practice, just the subordinate CA’s certificate) will carry the correct URLs for chain building and revocation checking. Step 5: Back Up the Root CA and Issue the Subordinate Certificate With the Root CA configured, we need to issue a certificate for the Issuing CA (subordinate). We’ll perform that in the next section from the Issuing CA’s side via a request file. Before taking the root offline, ensure you: Back up the CA’s private key and certificate: In the Certification Authority console, or via the CA Backup wizard, export the Root CA’s key pair and CA certificate. Protect this backup (store it offline in a secure location, e.g., on encrypted removable media in a safe). This backup is crucial for disaster recovery or if the Root CA needs to be migrated or restored. Save the Root CA Certificate: You will need the Root CA’s public certificate (*.crt) to distribute to other systems. Have it exported (Base-64 or DER format) for use on the Issuing CA and for clients. Initial CRL publication: Manually publish the first CRL so that it can be distributed. Open an elevated Command Prompt on the Root CA and run: certutil -crl This generates a new CRL file (in the CA’s configured CRL folder, typically %windir%\system32\CertSrv\CertEnroll). Take that CRL file and copy it to the designated distribution point (for example, to the CertEnroll directory on the Issuing CA’s web server, as per the HTTP URL configured). If using Active Directory for CRL distribution, you would also publish it to AD now (e.g., certutil -dspublish -f RootCA.crl on a domain-connected machine). In most lab setups, copying to an HTTP share is sufficient. With these tasks done, the Root CA is ready. At this point, disconnect or power off the Root CA and store it securely – it should remain offline except when it’s absolutely needed (like publishing a new CRL or renewing the subordinate CA’s certificate in the far future). Keeping the root CA offline maximizes its security by minimizing exposure to compromise. Best Practices for Securing the Root CA: The Root CA is the trust anchor, so apply stringent security practices: Physical security: Store the Root CA machine in a locked, secure location. If it’s a virtual machine, consider storing it on a disconnected hypervisor or a USB drive locked in a safe. Only authorized PKI team members should have access. An offline CA should be treated like crown jewels – offline CAs should be stored in secure locations. Minimal exposure: Keep the Root CA powered off and disconnected when not in use. It should not be left running or connected to any network. Routine operations (like issuing end-entity certs) should never involve the root. Admin access control: Limit administrative access on the Root CA server. Use dedicated accounts for PKI administration. Enable auditing on the CA for any changes or issuance events. No additional roles or software: Do not use the Root CA server for any other function (no web browsing, no email, etc.). Fewer installed components means fewer potential vulnerabilities. Protect the private key: Use an HSM if possible; if not, ensure the key is at least protected by a strong password and consider splitting knowledge of that password among multiple people (so no single person can activate the CA). Many organizations opt for an offline root key ceremony (see below) to generate and handle the root key with multiple witnesses and strict procedures. Keep system time and settings consistent: If the Root CA is powered off for long periods, ensure its clock is accurate whenever it is started (to avoid issuing a CRL or certificate with a wrong date). Don’t change the server name or CA name after installation (doing so invalidates issued certs). Periodic health checks: Even though offline, plan to turn on the Root CA at a secure interval (e.g., semi-annually or annually) to perform tasks like CRL publishing and system updates. Make sure to apply OS security updates during these maintenance windows, as offline does not mean immune to vulnerabilities (especially if it ever connects to a network for CRL publication or uses removable media). Deploying the Online Issuing CA Next, set up the Issuing CA server which will actually issue certificates to end entities in the lab. This server will be domain-joined (if using AD integration) and will obtain its CA certificate from the Root CA we just configured. Step 1: Prepare the Issuing CA Server Provision the server: Install Windows Server on a new machine (or VM) that will be the Issuing CA. Join this server to the Active Directory domain (e.g., Contoso.local). Being an enterprise CA, it needs domain membership to publish templates and integrate with AD security groups. Rename the server to something descriptive like ISSUINGCA for clarity. Assign a static IP and ensure it can communicate on the network. IIS for web enrollment (optional): If you plan to use the Web Enrollment or Certificate Enrollment Web Services, ensure IIS is installed. (The AD CS installation wizard can add it if you include those role services.) For this guide, we will include the Web Enrollment role so that the CertEnroll directory is set up for hosting certificate and CRL files. Step 2: Install AD CS Role on Issuing CA On the Issuing CA server, add the Active Directory Certificate Services role via Server Manager or PowerShell. This time, select both Certification Authority and Certification Authority Web Enrollment role services (Web Enrollment will set up the HTTP endpoints for certificate requests if needed). For example, using PowerShell: Install-WindowsFeature AD-Certificate, ADCS-Web-Enrollment -IncludeManagementTools After installation, launch the AD CS configuration wizard: Role Services: Choose Certification Authority (and Web Enrollment if prompted). Setup Type: Select Enterprise CA (since this CA will integrate with AD DS). CA Type: Select Subordinate CA (this indicates it will get its cert from an existing root CA). Private Key: Choose “Create a new private key” (we’ll generate a new key pair for this CA). Cryptography: If using an HSM here as well, select the HSM’s CSP/KSP for the issuing CA’s key. Otherwise, choose a strong key length (2048+ bits, SHA256 or better for hash). CA Name: Provide a name (e.g., “Contoso Issuing CA”). This name will appear as the Issuer on certificates it issues. Certificate Request: The wizard will ask how you want to get the subordinate CA’s certificate. Choose “Save a certificate request to file”. Specify a path, e.g., C:\CertRequest\issuingCA.req. The wizard will generate a request file that we need to take to the Root CA for signing. (Since our Root CA is offline, this file transfer might be via secure USB or a network share when the root is temporarily online.) CA Database: Choose locations or accept defaults for the certificate DB and logs. Finish the configuration wizard, which will complete pending because the CA doesn’t have a certificate yet. The AD CS service on this server won’t start until we import the issued cert from the root. Step 3: Integrate HSM on Issuing CA (Optional) If available, repeat the HSM setup on the Issuing CA: install HSM drivers, initialize it, and generate/secure the key for the subordinate CA on the HSM. Ensure you chose the HSM provider during the above configuration so that the issuing CA’s private key is stored in the HSM. Even though this CA is online, an HSM still greatly enhances security by protecting the private key from extraction. The issuing CA’s HSM may not require multiple custodians to activate (as it needs to run continuously), but should still be physically secured. Step 4: Obtain the Issuing CA’s Certificate from the Root CA Now we have a pending request (issuingCA.req) for the subordinate CA. To get its certificate: Transport the request to the Root CA: Copy the request file to the offline Root CA (via secure means – e.g., formatted new USB stick). Start up the Root CA (in a secure, offline setting) and open the Certification Authority console. Submit the request on Root CA: Right-click the Root CA in the CA console -> All Tasks -> Submit new request, and select the .req file. The request will appear in the Pending Requests on the root. Issue the subordinate CA certificate: Find the pending request (it will list the Issuing CA’s name). Right-click and choose All Tasks > Issue. The subordinate CA’s certificate is now issued by the Root CA. Export the issued certificate: Still on the Root CA, go to Issued Certificates, find the newly issued subordinate CA cert (you can identify it by the Request ID or by the name). Right-click it and choose Open or All Tasks > Export to get the certificate in a file form. If using the console’s built-in “Export” it might only allow binary; alternatively use the certutil command: certutil -dup <RequestID> .\ContosoIssuingCA.cer or simply open and copy to file. Save the certificate as issuingCA.cer. Also make sure you have a copy of the Root CA’s certificate (if not already done). Publish Root CA cert and CRL as needed: Before leaving the Root CA, you may also want to ensure the Root’s own certificate and latest CRL are available to the issuing CA and clients. If not already done in Step 5 of root deployment, export the Root CA cert (DER format) and copy the CRL file. You might use certutil -crl again if some time has passed since initial CRL. Now take the issuingCA.cer file (and root cert/CRL files) and move them back to the Issuing CA server. Step 5: Install the Issuing CA’s Certificate and Complete Configuration On the Issuing CA server (which is still waiting for its CA cert): Install the subordinate CA certificate: In Server Manager or the Certification Authority console on the Issuing CA, there should be an option to “Install CA Certificate” (if the AD CS configuration wizard is still open, it will prompt for the file; or otherwise, in the CA console right-click the CA name > All Tasks > Install CA Certificate). Provide the issuingCA.cer file obtained from the root. This will install the CA’s own certificate and start the CA service. The Issuing CA is now operational as a subordinate CA. Alternatively, use PowerShell: certutil -installcert C:\CertRequest\issuingCA.cer This installs the cert and associates it with the pending key. Trust the Root CA certificate: Because the Issuing CA is domain-joined, when you install the subordinate cert, it might automatically place the Root CA’s certificate in the Trusted Root Certification Authorities store on that server (and possibly publish it to AD). If not, you should manually install the Root CA’s certificate into the Trusted Root CA store on the Issuing CA machine (using the Certificates MMC or certutil -addstore -f Root rootCA.cer). This step prevents any “chain not trusted” warnings on the Issuing CA and ensures it trusts its parent. In an enterprise environment, you would also distribute the root certificate to all client machines (e.g., via Group Policy) so that they trust the whole chain. Import Root CRL: Copy the Root CA’s CRL (*.crl file) to the Issuing CA’s CRL distribution point location (e.g., C:\Windows\System32\CertSrv\CertEnroll\ if that’s the directory served by the web server). This matches the HTTP URL we configured on the root. Place the CRL file there and ensure it is accessible (the Issuing CA’s IIS might need to serve static .crl files; often, if Web Enrollment is installed, the CertEnroll folder is under C:\Inetpub\wwwroot\CertEnroll). At this point, the subordinate CA and any client hitting the HTTP URL can retrieve the root’s CRL. The subordinate CA is now fully established. It holds a certificate issued by the Root CA (forming a complete chain of trust), and it’s ready to issue end-entity certificates. Step 6: Configure Issuing CA Settings and Start Services Start the Certificate Services: If the CA service (CertSvc) isn’t started automatically, start or restart it. On PowerShell: Restart-Service certsvc The CA should show as running in the CA console with the name “Contoso Issuing CA” (or your chosen name). Configure Certificate Templates: Because this is an Enterprise CA, it can utilize certificate templates stored in Active Directory to simplify issuing common cert types (user auth, computer auth, web server SSL, etc.). By default, some templates (e.g., User, Computer) are available but not issued. In the Certification Authority console under Certificate Templates, you can choose which templates to issue (e.g., right-click > New > Certificate Template to Issue, then select templates like “User” or “Computer”). This lab guide doesn’t require specific templates but know that only Enterprise CAs can use templates. Templates define the policies and settings (cryptography, enrollment permissions, etc.) for issued certificates. Ensure you enable only the templates needed and configure their permissions appropriately (e.g., allow the appropriate groups to enroll). Set CRL publishing schedule: The Issuing CA will automatically publish its own CRL (for certificates it issues) at intervals. You can adjust the CRL and Delta CRL publication interval in the CA’s Properties > CRL Period. A common practice is a small base CRL period (e.g., 1 week or 2 weeks) for issuing CAs, because they may revoke user certs more frequently; and enable Delta CRLs (published daily) for timely revocation information. Make sure the CDP/AIA for the Issuing CA itself are properly configured too (the wizard usually sets LDAP and HTTP locations, but verify in the Extensions tab). In a lab, the default settings are fine. Web Enrollment (if installed): You can verify the web enrollment by browsing to http://<IssuingCA>/certsrv. This web UI allows browser-based certificate requests. It’s a legacy interface mostly, but for testing it can be used if your clients aren’t domain-joined or if you want a manual request method. In modern use, the Certificate Enrollment Web Service/Policy roles or auto-enrollment via Group Policy are preferred for remote and automated enrollment. At this stage, your PKI is operational: the Issuing CA trusts the offline Root CA and can issue certificates. The Root CA can be kept offline with confidence that the subordinate will handle all regular work. Validation and Testing of the PKI It’s important to verify that the PKI is configured correctly: Check CA status: On the Issuing CA, open the Certification Authority console and ensure no errors. Verify that the Issuing CA’s certificate shows OK (no red X). On the Root CA (offline most of the time), you can use the Pkiview.msc snap-in (Microsoft PKI Health Tool) on a domain-connected machine to check the health of the PKI. This tool will show if the CDPs/AIA are reachable and if certificates are properly published. Trust chain on clients: On a domain-joined client PC, the Root CA certificate should be present in the Trusted Root Certification Authorities store (if the Issuing CA was installed as Enterprise CA, it likely published the root cert to AD automatically; you can also distribute it via Group Policy or manually). The Issuing CA’s certificate should appear in the Intermediate Certification Authorities store. This establishes the chain of trust. If not, import the root cert into the domain’s Group Policy for Trusted Roots. A quick test: on a client, run certutil -config "ISSUINGCA\\Contoso Issuing CA" -ping to see if it can contact the CA (or use the Certification Authority MMC targeting the issuing CA). Enroll a test certificate: Try to enroll for a certificate from the Issuing CA. For instance, from a domain-joined client, use the Certificates MMC (in Current User or Computer context) and initiate a certificate request for a User or Computer certificate (depending on templates issued). If auto-enrollment is configured via Group Policy for a template, you can simply log on a client and see if it automatically receives a certificate. Alternatively, use the web enrollment page or certreq command to submit a request. The request should be approved and a certificate issued by "Contoso Issuing CA". After enrollment, inspect the issued certificate: it should chain up to "Contoso Root CA" without errors. Ensure that the certificate’s CDP points to the URL we set (and try to browse that URL to see the CRL file), and that the AIA points to the root cert location. Revocation test (optional): To test CRL behavior, you could revoke a test certificate on the Issuing CA (using the CA console) and publish a new CRL. On the client, after updating the CRL, the revoked certificate should show as revoked. For the Root CA, since it shouldn’t issue end-entity certs, you wouldn’t normally revoke anything except potentially the subordinate CA’s certificate (which would be a drastic action in case of compromise). By issuing a test certificate and validating the chain and revocation, you confirm that your two-tier PKI lab is functioning correctly. Maintaining the PKI: CRLs, Key Ceremonies, and Security Procedures Deploying the PKI is only the beginning. Proper maintenance and operational procedures are crucial to ensure the PKI remains secure and reliable over time. Periodic CRL Updates for the Offline Root: The Root CA’s CRL has a defined validity period (set during configuration, often 6 or 12 months for offline roots). Before the CRL expires, the Root CA must be brought online (in a secure environment) to issue a new CRL. It’s recommended to schedule CRL updates periodically (e.g., semi-annually) to prevent the CRL from expiring. An expired CRL can cause certificate chain validation to fail, potentially disrupting services. Typically, organizations set the offline root CRL validity so that publishing 1-2 times a year is sufficient. When the time comes: Start the Root CA (ensuring the system clock is correct). Run certutil -crl to issue a fresh CRL. Distribute the new CRL: copy it to the HTTP CDP location (overwrite the old file) and, if applicable, use certutil -dspublish -f RootCA.crl to update it in Active Directory. Verify that the new CRL’s next update date is extended appropriately (e.g., another 6 months out). Clients and the Issuing CA will automatically pick up the new CRL when checking for revocation. (The Issuing CA, if configured, might cache the root CRL and need a restart or certutil -setreg ca\CRLFlags +CRLF_REVCHECK_IGNORE_OFFLINE tweak if the root CRL expires unexpectedly. Keeping the schedule prevents such issues.) Issuing CA CRL and OCSP: The Issuing CA’s CRLs are published automatically as it is online. Ensure the IIS or file share hosting the CRL is accessible. Optionally, consider setting up an Online Responder (OCSP) for real-time status checking, especially if CRLs are large or you need faster revocation information. OCSP is another AD CS role service that can be configured on the issuing CA or another server to answer certificate status queries. This might be beyond a simple lab, but it’s worth mentioning for completeness. Key Ceremonies and Documentation: For production environments (and good practice even in labs), formalize the process of handling CA keys in a Key Ceremony. A key ceremony is a carefully controlled process for activities like generating the Root CA’s key pair, installing the CA, and signing subordinate certificates. It often involves multiple people to ensure no single person has unilateral control (principle of dual control) and to witness the process. Best practices for a Root CA key ceremony include: Advance Planning: Create a step-by-step script of the ceremony tasks. Include who will do what, what materials are needed (HSMs, installation media, backup devices, etc.), and the order of operations. Multiple trusted individuals present: Roles might include a Ceremony Administrator (leads the process), a Security Officer (responsible for HSM or key material handling), an Auditor (to observe and record), etc. This prevents any one person from manipulating the process and increases trust. Secure environment: Conduct the ceremony in a secure location (e.g., a locked room) free of recording devices or unauthorized personnel. Ensure the Root CA machine is isolated (no network), and ideally that BIOS/USB access controls are in place to prevent any malware. Generate keys with proper controls: If using an HSM, initialize and generate the key with the required number of key custodians each providing part of the activation material (e.g., smartcards or passphrases). Immediately back up the HSM partition or key to secure media (requiring the same custodians to restore). Sign subordinate CA certificate: As part of the ceremony, once the root key is ready, sign the subordinate’s request. This might also be a witnessed step. Document every action: Write down each command run, each key generated, serial numbers of devices used, and have all participants sign an acknowledgment of the outcomes. Also record the fingerprints of the generated Root CA certificate and any subordinate certificate to ensure they are exactly as expected. Secure storage: After the ceremony, store the Root CA machine (if it’s a laptop or VM) and HSM tokens in a tamper-evident bag or safe. The idea is to make it evident if someone tries to access the root outside of an authorized ceremony. While a full key ceremony might be overkill for a small lab, understanding these practices is important. Even in a lab, you can simulate some aspects (for learning), like documenting the procedure of taking the root online to sign the request and then locking it away. These practices greatly increase the trust in a production PKI by ensuring transparency and accountability for critical operations. Backup and Recovery Plans: Both CAs’ data should be regularly backed up: For the Root CA: since it’s rarely online, backup after any change. Typically, you’d back up the CA’s private key and certificate once (right after setup or any renewal). Store this securely offline (separate from the server itself). Also back up the CA database if it ever issues more than one cert (for root it might not issue many). For the Issuing CA: schedule automated backups of the CA database and private key. You can use the built-in certutil -backup or Windows Server Backup (which is aware of the AD CS database). Keep backups secure and test restoration procedures. Having a documented recovery procedure for the CA is crucial for continuity. Also consider backup of templates and any scripts. Maintain spare hardware or VMs in case you need to restore the CA on new hardware (especially for the root, having a procedure to restore on a new machine if the original is destroyed). Security maintenance: Apply OS updates to the CAs carefully. For the offline root, patch it offline if possible (offline servicing or connecting it briefly to a management network). For the issuing CA, treat it as a critical infrastructure server: limit its exposure (firewall it so only required services are reachable), monitor its event logs (enable auditing for Certificate Services events, which can log each issuance and revocation), and employ anti-malware tools with caution (whitelisting the CA processes to avoid interference). Also, periodically review the CA’s configuration and certificate templates to ensure they meet current security standards (for example, deprecate any weak cryptography or adjust validity periods if needed). By following these maintenance steps and best practices, your two-tier PKI will remain secure and trustworthy over time. Remember that PKI is not “set and forget” – it requires operational diligence, but the payoff is a robust trust infrastructure for your organization’s security. Additional AD CS Features and References Active Directory Certificate Services provides more capabilities than covered in this basic lab. Depending on your needs, you might explore: Certificate Templates: We touched on templates; they are a powerful feature on Enterprise CAs to enforce standardized certificate settings. Administrators can create custom templates for various use cases (SSL, S/MIME email, code signing) and control enrollment permissions. Understanding template versions and permissions is key for enterprise deployments. (Refer to Microsoft’s documentation on Certificate template concepts in Windows Server for details on how templates work and can be customized.) Web Services for Enrollment: In scenarios with remote or non-domain clients, AD CS offers the Certificate Enrollment Web Service (CES) and Certificate Enrollment Policy Web Service (CEP) role services. These allow clients to fetch enrollment policy information and request certificates over HTTP or HTTPS, even when not connected directly to the domain. They work with the certificate templates to enable similar auto-enrollment experiences over the web. See Microsoft’s guides on the Certificate Enrollment Web Service overview and Certificate Enrollment Policy Web Service overview for when to use these. Network Device Enrollment Service (NDES): This AD CS role service implements the Simple Certificate Enrollment Protocol (SCEP) to allow devices like routers, switches, and mobile devices to obtain certificates from the CA without domain credentials. NDES acts as a proxy (Registration Authority) between devices and the CA, using one-time passwords for authentication. If you need to issue certificates to network equipment or MDM-managed mobile devices, NDES is the solution. Microsoft Docs provide a Network Device Enrollment Service(NDES) overview and even details on using a policy module with NDES for advanced scenarios (like customizing how requests are processed or integrating with custom policies). Online Responders (OCSP): As mentioned, an Online Responder can be configured to answer revocation status queries more efficiently than CRLs, especially useful if your CRLs grow large or you have high-volume certificate validation (VPNs, etc.). AD CS’s Online Responder role service can be installed on a member server and configured with the OCSP Response Signing certificate from your Issuing CA. Monitoring and Auditing: Windows Servers have options to audit CA events. Enabling auditing can log events such as certificate issuance, revocation, or changes to the CA configuration. These logs are important in enterprise PKI to track who did what (for compliance and security forensics). Also, tools like the PKI Health Tool (pkiview.msc) and PowerShell cmdlets (like Get-CertificationAuthority, Get-CertificationAuthorityCertificate) can help monitor the health and configuration of your CAs. Conclusion By following this guide, you have set up a secure two-tier PKI environment consisting of an offline Root CA and an online Issuing CA. This design, which uses an offline root, is considered a security best practice for enterprise PKI deployments because it reduces the risk of your root key being compromised. With the offline Root CA acting as a hardened trust anchor and the enterprise Issuing CA handling day-to-day certificate issuance, your lab PKI can issue certificates for various purposes (HTTPS, code signing, user authentication, etc.) in a way that models real-world deployments. As you expand this lab or move to production, always remember that PKI security is as much about process as technology. Applying strict controls to protect CA keys, keeping software up to date, and monitoring your PKI’s health are all part of the journey. For further reading and official guidance, refer to these Microsoft documentation resources: 📖 AD CS PKI Design Considerations: PKI design considerations using Active Directory Certificate Services in Windows Server helps in planning a PKI deployment (number of CAs, hierarchy depth, naming, key lengths, validity periods, etc.). This is useful to read when adapting this lab design to a production environment. It also covers configuring CDP/AIA and why offline roots usually don’t need delta CRLs. 📖 AD CS Step-by-Step Guides: Microsoft’s Test Lab Guide Test Lab Guide: Deploying an AD CS Two-Tier PKI Hierarchy walk through a similar scenario.
Sharepoint deleting data and sites
Hello, We have noticed an issue that started about a year ago in which data is being deleted in Sharepoint. When looking at this data in the Recycle bin, it will show it was modified/deleted by specific Users but these user deny ever doing such a thing. It is at the point in which we believe the Sharepoint system itself is actually deleting data possibly due to a bug. It would be odd for the employees tagged in the Modified By field to have deleted it. Our data is backed up so recovering any deleted items isn't the issue. The issue is that we are trying to get Microsoft to investigate. We have submitted tickets through the MS 365 portal but they state they only work on break/fix issues. Any recommendations? I can see searching the internet this issue has come up for many others in the past.
Move files from Account A to Account B 165 GB data
I’ve been using Microsoft Office 365 Family for several years, sharing it with my family members. We have 6 accounts, each with 1 TB of storage. One of my accounts has now reached 985 GB, so I need to transfer files from Account A (my account) to Account B (my wife’s account). These files mainly consist of photos and videos — over 200,000 files in total. I tried transferring a 6 GB wedding shoot (.ISO format), but it took more than an hour. Re-downloading and uploading all the data isn’t feasible as my internet connectivity is limited to 100 mbps only. I’m looking for the best and most efficient way to move these files directly between OneDrive accounts.Excel Tools for Network & Windows
Excel Tools for Network & Windows Some time ago I already shared an earlier version of this project. Since then, I have added several new features. These tools are based on functionalities that already exist in Windows and its associated software. I have consolidated them into a single Excel-based interface, allowing all tools to be executed directly from Excel. The files are free for private use. For business or enterprise environments, a more comprehensive toolbox can be developed, enabling direct support, repair, management, monitoring, and control of users and systems. Everything can be customized according to specific requirements — the scope depends solely on the desired functionality, time investment, and budget. I appreciate any positive feedback, suggestions, or constructive tips. If this project is not of interest to you, please feel free to ignore it. Thank you, and I wish everyone happy holidays.How does local OneDrive determine if a local file needs to be updated?
When using multiple computers to edit a OneDrive file, a computer often fails to recognize its local copy needs to be updated, even though the file on all computers is set to "Always keep on this device." This means changes are lost with no conflict error generated. Is the OneDrive algorithm for deciding when to update a local version of a file documented anywhere? Usually when a change is made to a file, it starts uploading to the cloud within seconds. Within several seconds after the changed file is uploaded, other computers will recognize their local copy is outdated and will begin downloading the changed version. That is the expected behavior. But often, that doesn't happen. The outdated version is used to make new changes. Those new changes are uploaded successfully. No conflict warning is generated. The earlier changes are lost forever. I have not found any documentation on how local Windows OneDrive decides if its local version of a file needs to be updated. Is it looking at file size? Timestamps? If timestamps, is there a margin of time sync differences? Does the OneDrive metadata include the source device of the last upload? Not knowing any of this I cannot troubleshoot the problem much beyond establishing that the problem is not with uploading changes. OneDrive local is reliably uploading changes. MD5 hash codes in the cloud match the hash of the changed file on the source computer. I don't have time to jump through hoops with someone at frontline Microsoft support who doesn't know any more about the algorithm than I know in order to get the issue escalated to someone with the information needed to pinpoint the issuse.
Name Manager using for create name which is contain atleast two name.
Hello. I creating somthing in excel with tables. These tables has thier own name, and can be dynamic or not. Any way. I using list in cell to select each data from a tables column. For that I created names with the content of a column. Unfortunatly i had to make a kind of name which is contain atleast 2 columns. These can grow dynamicly. So I think a plus helper tabel is not the right sollution for that. I think about 3 kind of solution. 1. =UNIQUE( VSTACK( INDEX(Tabla1[#Data];0;MATCH("Type_name";Tabla1[#Headers];0)); INDEX(Tabla2[#Data];0;MATCH("Column_name";Tabla2[#Headers];0)) ) output #name? 2. =UNIQUE(VSTACK(Lista_A; Lista_B)) lista_A as a name output #name? 3. created a helper table with the existing names. Created another name and use the table in it. output was the elements contained by the helper tabel, and the lista_A and lista_B tables each dedicated column. So How can i create list for a cell or cells from two column which are dynamicly growing, without a user needs to touch the core modell? Best Balázs
Finding time duration between a start date & time with end date & time
Hi all! I'm looking for any formula or power query to calculate a total time duration within a day, given the start date, start time, end date, end time. Most of the dates will equal the same but there are some with the end date being the next day. I'd like to be able to exclude any overlaps as well. Currently, I have a large embedded IF formula: =IF(AND($G4=$O4,$H4<$H5,$P4>=$H5,$P4<$P5,$H4<$H3),$P4-$H4,IF(AND($G4=$O4,$G4>$G3,$H4<$H3,$P4<$P3,$H4<$P3,$P4<$P5),$P4-$H4,IF(AND($G4=$O4,$H4>$H3,$H4>=$P3,$P4>$P3),$P4-$H4,IF(AND($G4=$O4,$H4=$P4),0,IF(AND($G4=$O4,$H4<$P3,$P4<=$P3),0,IF(AND($G4<$O4,$H4<$P3,$P4>$H4),($P4+1)-$P3,IF(AND($G4=$O4,$O4<$G5,$O4<$O5,$H4<$P3,$P4>$P3),$P4-$P3,IF(AND($G4=$O4,$G4>$G3,$H4>$H3,$P4>$P3,$H4>$P3),$P4-$H4,IF(AND($G4=$O4,$G4<$O5,$P4>$P3,$P4>$H5,$H4>$H3,$H4<$H5),0,IF(AND($G4=$O4,$O4=$G5,$H4<$P3,$P4>$H5,$P4>$P3,$P4>$P5,$P2>$P3),$P4-$P2,IF(AND($G4=$O4,$H4<$P3,$P4>$P3,$P4>$P5),$P4-$P3,IF(AND($G4=$O4,$H4<$P3,$P4>$P3,$H4<$H5,$P4<$P5),$P4-$P3,IF(AND($G4=$O4,$H4<$H5,$H4<$P3,$P4>$P3,$P4>$P5),$P4-$P3,IF(AND($G4=$O4,$O4=$G5,$H4<$P3,$P4>$H5,$P4>$P3),$P4-$P2,IF(AND(ISBLANK($O4),ISBLANK($P4)),0,IF(AND($G4<$O4,$H4<$P3,$P4<$H4),($P4+1)-$P3)))))))))))))))) This seems to work for the most part but there are a few that I just can't get. I also pulled up my query and started to enter in the time durations manually and it couldnt come up with anything automatic for me. There must be an easier way for me to do this other than trying to create an IF formula for each answer that turns up incorrect. I have a screen shot below.Microsoft 365 admin center support
I am extremely disappointed with the customer support experience associated with Microsoft 365 Business. As a business customer, I expected a reliable support system. Unfortunately, the reality has been the opposite, and I feel compelled to caution others to carefully consider their options before committing their hard-earned money to a Microsoft 365 business subscription. After purchasing Microsoft Business licenses and transitioning my services from GoDaddy to Microsoft, I lost access to my global admin credentials. This should be a straightforward issue for support to resolve, yet it has turned into a prolonged and frustrating ordeal. For the past two weeks, I have been trying to obtain assistance without success. I contacted Microsoft support over ten days ago and received a ticket, with the assurance that someone would contact me within 24 hours. No one has reached out to me—not in 24 hours, and not in the ten days since. I attempted to escalate the issue, but even then, no meaningful support was provided. This level of customer service is unacceptable for any business solution, especially one that organizations rely on for critical operations. It is unreasonable to expect customers to run their businesses effectively without access to timely and competent support. At this point, I am requesting a refund for the service that has not been delivered, and I strongly urge Microsoft to address the shortcomings in its support system. The support I received from GoDaddy in the past was significantly better. I hope no other business has to experience this level of frustration, and I sincerely urge Microsoft to acknowledge and fix these issues.
Best Practice guide for stretched HA farm?
Hi, Im planning a SharePoint Subscription farm over 2 data centers. Should be pretty simple. Farm will consist of: dc 1: 1 spfe, 1 spapp, 1 sql dc 2: 1 spfe, 1 spapp, 1 sql Sql servers will be AlwaysOn. Im not sure how to set up the sp servers. Is there a preferred way to set it up, with how to? Our domains have 10gb connections so should be more than sufficient for stretched and HA. Can CA site be hosted from multiple servers? How are IPs/DNS/certs handled? What else do I need to get my head around? Thanks. Swan
