Microsoft Connected Cache HTTPS Mandate: Strategic Implications and Implementation Guide

What Changed: Microsoft's HTTPS Mandate for Connected Cache

Effective June 16, 2026, Microsoft will enforce HTTPS content delivery for customers using Microsoft Connected Cache for Enterprise and Education environments. This policy change represents a fundamental shift in how Intune Win32 apps are delivered across organizational networks. The Connected Cache service, designed to localize content delivery and reduce bandwidth consumption, will require HTTPS configuration to maintain its performance optimization benefits.

Without proper HTTPS implementation, client devices will still fetch requested content but will fall back to Microsoft's Content Delivery Network (CDN), eliminating the localized caching advantages that Connected Cache provides. This fallback mechanism ensures content availability but negates the primary business case for deploying Connected Cache in the first place.

The enforcement timeline gives organizations approximately two years to prepare their environments, though early adoption is recommended to validate configurations and address potential compatibility issues with existing infrastructure.

Provider Comparison: Connected Cache Across Cloud Environments

Microsoft Connected Cache operates differently across various cloud deployment models, each presenting unique implementation considerations:

On-Premises Deployments

Organizations maintaining Connected Cache on-premises face the most significant configuration changes, as they control the entire certificate lifecycle. These deployments typically use:

• Windows Server 2022 or 2025 as the host platform
• Public certificate authority (CA)-signed TLS certificates
• Direct integration with organizational PKI infrastructure

The implementation process requires careful coordination between IT security teams (managing certificates) and infrastructure teams (configuring the cache nodes).

Azure-Hosted Deployments

For Connected Cache deployed within Azure, Microsoft manages more of the underlying infrastructure, but customers still need to:

• Configure TLS certificates for their specific cache instances
• Manage certificate renewal processes
• Ensure proper firewall rules allow HTTPS traffic

Azure-hosted deployments benefit from built-in integration with Azure Key Vault for certificate management, though this capability is not yet fully utilized by Connected Cache.

Hybrid and Multi-Cloud Environments

Organizations with hybrid deployments face the most complex scenarios, as they must:

• Standardize certificate management across different platforms
• Ensure consistent security policies across on-premises and cloud resources
• Address potential network segmentation challenges

Linux-based deployments (typically Ubuntu or RHEL) follow the same fundamental workflow but with simplified implementation through bash scripts rather than PowerShell. The core requirements remain identical regardless of the underlying platform.

Business Impact: Strategic Considerations for Organizations

The HTTPS mandate for Connected Cache extends beyond a simple technical compliance requirement. Organizations must consider several strategic implications:

Bandwidth and Cost Implications

Connected Cache reduces bandwidth consumption by approximately 30-70% for Intune content delivery, depending on organization size and network topology. Without HTTPS configuration, organizations will lose these savings, potentially leading to:

• Increased bandwidth costs, especially for distributed deployments
• Higher egress fees from branch locations to central data centers
• Potential need for network infrastructure upgrades

Security and Compliance Considerations

The HTTPS enforcement aligns with broader industry trends toward encrypted content delivery. Organizations should view this as an opportunity to:

• Enhance overall security posture for content delivery
• Meet compliance requirements for encrypted data in transit
• Reduce exposure to potential man-in-the-middle attacks

Operational Impact

Implementing HTTPS support for Connected Cache affects multiple operational areas:

• Certificate management lifecycle must be formalized
• Monitoring capabilities need enhancement to track certificate validity
• Renewal processes must be established before the June 2026 deadline

Organizations with Connected Cache deployments should assess their current certificate management maturity and identify gaps in processes, tools, and expertise.

Implementation Guide: Enabling HTTPS for Connected Cache

The implementation process follows a standardized workflow regardless of the underlying platform. Organizations should approach this as a structured project with clear phases and validation checkpoints.

Phase 1: Environment Preparation

Before beginning the HTTPS configuration, verify the following prerequisites:

• Connected Cache software version 2.0.0.2112 or higher
• Confirm hostname or IP address used by client devices
• Ensure port 443 is available on the cache node
• Verify TLS inspection policies won't interfere with certificate validation

For Windows-based deployments, the process involves PowerShell scripts that interact with a Windows Subsystem for Linux (WSL) container. Linux deployments use bash scripts directly.

Phase 2: Certificate Generation

The critical first step is generating a Certificate Signing Request (CSR) directly on the Connected Cache node. This process cannot be performed externally, as Microsoft Connected Cache must generate and retain the private key.

Key considerations during CSR generation:

• Subject and Subject Alternative Name (SAN) must match exactly how client devices connect
• If clients use FQDN, include that FQDN; if connecting via IP, include that IP
• Mismatches will cause clients to bypass Connected Cache during TLS negotiation

The generateCsr script creates the CSR and stores it in the certificates folder, along with detailed logs for troubleshooting.

Phase 3: Certificate Signing

Once the CSR is generated, it must be signed by an appropriate Certificate Authority:

• Organizations can use internal PKI (ADCS or equivalent)
• External CAs like DigiCert or Let's Encrypt are supported
• Cloud PKI solutions are not compatible due to SCEP requirements

The resulting certificate must be in unencrypted .crt format, as password-protected .pfx files are not currently supported.

Phase 4: Certificate Import

After receiving the signed certificate, import it back to the Connected Cache node using the importCert command. This process:

• Verifies the certificate matches the original CSR and private key
• Updates the Connected Cache configuration
• Restarts the service with the new certificate

Import failures may occur on certain configurations (Windows Server 2022/2025 with gMSA or Windows 11 with local user accounts). These are known issues with fixes pending in upcoming releases.

Phase 5: Validation

Complete end-to-end validation through two distinct phases:

1. Server-side validation: Confirm Connected Cache is listening on port 443 with the correct TLS certificate
2. Client-side validation: Verify client devices can trust and use the certificate for content retrieval

The validation process includes both browser-based and command-line tests to ensure complete functionality.

Phase 6: Ongoing Maintenance

Plan for certificate lifecycle management:

• Monitor certificate validity and approaching expiration dates
• Establish renewal processes starting at least 60 days before expiration
• Consider automating renewal for larger deployments
• Test renewal processes on non-production nodes first

Troubleshooting Common Issues

Organizations may encounter several known issues during implementation:

1. ImportCert failures on Windows Server 2022/2025 with gMSA

   • This is a documented issue with an upcoming fix
   • The import process can still be run safely

2. ImportCert hanging on version 2119_e

   • A buffer bug causes indefinite hanging
   • Rerunning the script or waiting for the update resolves the issue

3. Certificate trust issues

   • Typically caused by SAN/hostname mismatches
   • TLS inspection policies may interfere with certificate validation

Detailed logs are available in the ...\Certificates\logs folder for each step of the process, providing comprehensive troubleshooting information.

Strategic Recommendations for Organizations

Given the two-year implementation window, organizations should adopt a phased approach:

Assessment Phase (Now - 6 months)

• Inventory all Connected Cache deployments
• Evaluate current certificate management capabilities
• Identify potential compatibility issues with existing infrastructure

Pilot Implementation (6-18 months)

• Implement HTTPS on a limited number of cache nodes
• Refine processes based on pilot experience
• Develop documentation and playbooks for broader deployment

Full Deployment (18-24 months)

• Implement HTTPS across all Connected Cache nodes
• Establish ongoing monitoring and renewal processes
• Conduct final validation before the June 2026 deadline

Organizations with complex or distributed environments should consider engaging Microsoft partners or consultants with Connected Cache expertise to ensure smooth implementation.

Conclusion

Microsoft's HTTPS mandate for Connected Cache represents both a compliance requirement and an opportunity to enhance security posture. While the implementation process is well-documented, organizations should approach this as a strategic project rather than a technical configuration task.

The two-year implementation window provides sufficient time for thorough preparation, but early action is recommended to address potential challenges and establish robust certificate management processes. By treating this as an opportunity to strengthen content delivery security rather than merely a compliance checkbox, organizations can ensure their Connected Cache deployments continue to deliver optimal performance while meeting evolving security requirements.

For detailed technical guidance, refer to Microsoft's official documentation:

• HTTPS Support for Microsoft Connected Cache Overview
• Configure HTTPS on Windows
• Configure HTTPS on Linux

This implementation will position organizations to maintain the performance benefits of Connected Cache while meeting Microsoft's security requirements for the modern enterprise content delivery landscape.