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yanxxu's avatar
yanxxu
Icon for Microsoft rankMicrosoft
Feb 03, 2026

Cannot enroll azure vm(windows 24H2) in Microsoft company portal

I created a windows VM in Azure. To access company resources on this machine, I attempted to enroll the device through the Company Portal. However, the enrollment failed while setting up the work or school account, with the error message “This connection isn’t secure.” 

How should I fix this issue?

Intune

5 Replies

  • Bogdan_Guinea's avatar
    Bogdan_Guinea
    Steel Contributor
    Feb 03, 2026

    yanxxu​ 

    Hi,

    how is your VM’s outbound traffic routed (direct to internet, via Azure Firewall, via on‑prem proxy over VPN, etc.) it could be a SSL Inspection.

    Do your User have a Intune License?

    Good luck!

    • yanxxu's avatar
      yanxxu
      Icon for Microsoft rankMicrosoft
      Feb 03, 2026

      Thx Bogdan_Guinea​ .

       

      My physical machine can be enrolled successfully and it looks I have the license.

      How could I check if it is due to SSL Inspection?

       

      • Bogdan_Guinea's avatar
        Bogdan_Guinea
        Steel Contributor
        Feb 04, 2026

        Hi,

        i would go and try the link from you first share, try to open it in your browser and see if its loading or not, or a certificate warning.

        https://enterpriseenrollment-s.manage-beta.microsoft.com (or the standard enterpriseenrollment-s.manage.microsoft.com)

        Proxy check also. netsh winhttp show proxy.

        But if its working, thats fine or not 🙂

         

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