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Quick Assist is unable to match security requirements on the helper site

Mikhail Samodurov 0 Reputation points
2025-12-09T11:13:30.94+00:00

Hello,

There's been an ongoing issue with Quick Assist for at least the last 6 months.

One of our corporate VPN gateways doesn't allow helpers to connect due to "Minimum security requirements on the helper side" (see attachments).

All network exceptions for the Microsoft domains were made, and settings currently match those of the other VPN gateway (where everything works).

We use a hybrid identity scheme, using Microsoft Entra as IdP for both helper and target.

The issue isn't related to a specific helper or target device, as devices are up to date and everything works on another VPN gateway.

I'm aware that Quick Assist isn't an enterprise product, but it was helpful for the initial configuration of devices, and we can't afford Intune, so we can't use Remote Help.

Is there a chance our IP was blacklisted? If so, how can we appeal?

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Windows for business | Windows 365 Enterprise
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  1. Harry Phan 10,535 Reputation points Independent Advisor
    2025-12-09T13:53:45.3133333+00:00

    Hi Mikhail Samodurov

    There’s no public evidence that Quick Assist uses IP blacklisting, but VPN routing or TLS configurations may be triggering Microsoft’s minimum security checks. An appeal process isn’t documented, but I’ll guide you through next steps 🙂

    Here are a few steps you can take:

    Compare TLS inspection, split tunneling, and proxy behavior between the two VPN gateways. Even subtle differences can affect Quick Assist’s handshake.

    Ensure outbound access to all required Microsoft domains and services, including those used by Quick Assist (e.g., *.msftconnecttest.com, *.support.microsoft.com).

    Test Quick Assist outside the VPN to confirm the issue is gateway-specific.

    Use the “Get Help” app or Microsoft Q&A forums to report the issue, as Quick Assist doesn’t have dedicated enterprise support channels.

    If this answer helps clarify the situation, please hit “Accept Answer” 🙂.

    Harry.

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