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VPN Split-Tunnel DNS Mismatch (Internal Names Fail)

Troubleshoot split-tunnel VPN sessions where internal names fail while VPN appears connected. This troubleshooting guide is mirrored from the Support Portal knowledge base for quick access in Corporate Tech Fixes.

Severity: HighAdmin Required
Estimated Fix Time

10-20 min

Access Level

Admin Required

Total Steps

9

Author & Verification

Tamem J

IT Solutions Engineer

Last verified: March 3, 2026

Runbooks and troubleshooting guides are reviewed for enterprise-safe usage and avoid security bypass patterns.

Tested on Windows 11 23H2Tested on macOS Sequoia 15

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  • Enterprise Microsoft 365 Administration
  • Endpoint Management (Intune, Jamf, Kandji)
  • Identity & Access (Entra ID, Okta)
#vpn#split-tunnel#dns#internal-names#networking#routing#support-kb#windows#macos

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Step-by-Step Resolution

Expand each section as needed

  1. 1

    Symptoms

    Info

    Recommended validation or troubleshooting step

    - VPN is connected but internal hostnames do not resolve. - Internal resources work by IP but fail by DNS name. - Issue varies after reconnect or network changes.

  2. 2

    Likely Causes

    Info

    Recommended validation or troubleshooting step

    - DNS servers/search suffixes not applied correctly via tunnel. - Local DNS overrides enterprise resolution path. - Split-tunnel route policy and DNS scope mismatch.

  3. 3

    Confirm scope, user impact, and reproduction

    Info

    Recommended validation or troubleshooting step

    Document whether the issue affects one user, multiple users, or multiple devices. Confirm exact error messages, recent changes (password reset, update, network change), and whether the same issue reproduces in web vs desktop workflows where applicable.

  4. 4

    Validate prerequisites and application/session state

    Info

    Recommended validation or troubleshooting step

    Confirm the user is signed in with the correct corporate account, system time is accurate, network/VPN connectivity is stable, and the application is not running in offline or limited mode.

  5. 5

    Run safe diagnostics from the Commands section

    Info

    Recommended validation or troubleshooting step

    Use the command snippets below to collect non-destructive diagnostics. Capture output in the ticket when escalation may be required. Avoid deleting profiles, cached credentials, or managed app data unless the runbook or admin approval explicitly allows it.

  6. 6

    Apply safe remediation steps

    Info

    Recommended validation or troubleshooting step

    - Capture DNS server/search suffix state while VPN is active. - Test internal resources by hostname and IP for comparison. - Reconnect VPN and compare route/DNS outputs. - Escalate for profile-level DNS/split-tunnel policy correction.

  7. 7

    Escalate when access, policy, or security controls are involved

    Warning

    Review carefully before proceeding

    - Multiple users on same VPN profile are affected. - Issue started after VPN profile or client updates. - Requested workaround bypasses managed security controls.

    Admin review or admin rights may be required for this step.

  8. 8

    Split-tunnel DNS diagnostics

    Command

    Includes a copyable command block

    Command
    # Windows
    ipconfig /all
    Resolve-DnsName intranet.company.local
    route print
     
    # macOS
    scutil --dns
    nslookup intranet.company.local
    netstat -rn
  9. 9

    When to Escalate to IT / Security

    Warning

    Review carefully before proceeding

    - Multiple users on same VPN profile are affected. - Issue started after VPN profile or client updates. - Requested workaround bypasses managed security controls.

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