Important note about SSL VPN compatibility for 20.0 MR1 with EoL SFOS versions and UTM9 OS. Learn more in the release notes.

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SSL VPN client ready for deployment with tools like SCCM?

It’s useless to deploy instructions to every user how to login to User Portal (that we don’t want to use), and so on. So, how to export all configurations, and so on so we can create package for SCCM deploy ready.

Also, this is bad because every time when new user joins the company we need to export user certificate. But at least how to automate initial process? where can we export all user certs...



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  • Due to how Sophos implements OpenVPN, you're going to be forced to either export out of, or import into, Sophos.

    • I'm not sure if Sophos requires all SSL VPN users to have Sophos user accounts, but if not, the latter step could be skipped and all that would be required to give the user are the four normal openvpn files: CA cert, user cert, user key, and client config (or a p12 and client config).  Since the CA cert and client config remains unchanged from user to user, the only custom files would be the client cert and key.

    • Provided one has the three openssl commands (csr, sign, p12 export) at the ready (a command or shell script could automate all three), from start to finish, each [import/export] takes the same amount of time (a few minutes).  The only way I could see the process being streamlined is if the option is ticked for same common name usage, which should be used extremely carefully and only in very specific environments due to the massive security risk it poses.   If a Sophos user account is required for any accessing OpenVPN, it would be less of a headache for you to simply provide them access to the user portal.
      • I personally dislike the lack of customization in the Sophos openssl.cnf (as well as the reliance on obsolete methods in OpenVPN, such as ns cert type and net30 usage), so I always generate my certs on my PC, then import the p12s into Sophos.  Generating the SSL certs off of Sophos provides the ability to specify SAN and EKU values, and if one does choose to generate certs off of Sophos, one must ensure under the SAN profile that user certs have email.1 listed first, and it must be the user's Sophos user email (this ensures RFC822 is specified under SAN, and without this, it will be impossible for the user to authenticate) and hosts must list their primary DNS name with DNS.1 being the first value (I've had issues with Sophos if this isn't specified as the first value under SAN, especially with the WebAdmin/host cert).  EKU can also be set for server and client auth, and if these are set, and one has a warranty, tech support must be consulted for permission to remove "remote-cert-tls server" from the default openvpn config, adding instead "remote-cert-ku f8" (For an explanation: https://www.v13.gr/blog/?p=386)

      Another option may be an ipsec/html5 vpn

      SilverStone DS380 | AsRock C2750D4I | Alienware 18 In Win Chopin | SuperMicro A1SRi-2758F
      2.4gHz 8C C2750 ; 32GB ECC | 2.5gHz 4C i7 4710MQ ; 32GB 2.4gHz 8C C2758 ; 32GB ECC
      Vantec 4C USB3 PCIe UGT-PCE430-4C | 8GB AMD SLI R9 M290x |
      SSD  | 850 EVO: 120GB | 1TB ; mSATA: 1TB (2) | 850 Pro: 128GB ; 850 EVO: 1TB
      HDD | Seagate: { ST4000VN000 (8) } Z2 ; { HGST HTS721010A (3) } Z2 |
      FreeNAS 11.2 | { PNY Turbo USB3 32GB (2) } Mirror | Win 10 Pro | ESXi 6.7: Sophos UTM 9.6

      Various Wikis, Scripts, & Configs | Prebuilt OpenSSL Config

    Reply
    • Due to how Sophos implements OpenVPN, you're going to be forced to either export out of, or import into, Sophos.

      • I'm not sure if Sophos requires all SSL VPN users to have Sophos user accounts, but if not, the latter step could be skipped and all that would be required to give the user are the four normal openvpn files: CA cert, user cert, user key, and client config (or a p12 and client config).  Since the CA cert and client config remains unchanged from user to user, the only custom files would be the client cert and key.

      • Provided one has the three openssl commands (csr, sign, p12 export) at the ready (a command or shell script could automate all three), from start to finish, each [import/export] takes the same amount of time (a few minutes).  The only way I could see the process being streamlined is if the option is ticked for same common name usage, which should be used extremely carefully and only in very specific environments due to the massive security risk it poses.   If a Sophos user account is required for any accessing OpenVPN, it would be less of a headache for you to simply provide them access to the user portal.
        • I personally dislike the lack of customization in the Sophos openssl.cnf (as well as the reliance on obsolete methods in OpenVPN, such as ns cert type and net30 usage), so I always generate my certs on my PC, then import the p12s into Sophos.  Generating the SSL certs off of Sophos provides the ability to specify SAN and EKU values, and if one does choose to generate certs off of Sophos, one must ensure under the SAN profile that user certs have email.1 listed first, and it must be the user's Sophos user email (this ensures RFC822 is specified under SAN, and without this, it will be impossible for the user to authenticate) and hosts must list their primary DNS name with DNS.1 being the first value (I've had issues with Sophos if this isn't specified as the first value under SAN, especially with the WebAdmin/host cert).  EKU can also be set for server and client auth, and if these are set, and one has a warranty, tech support must be consulted for permission to remove "remote-cert-tls server" from the default openvpn config, adding instead "remote-cert-ku f8" (For an explanation: https://www.v13.gr/blog/?p=386)

        Another option may be an ipsec/html5 vpn

        SilverStone DS380 | AsRock C2750D4I | Alienware 18 In Win Chopin | SuperMicro A1SRi-2758F
        2.4gHz 8C C2750 ; 32GB ECC | 2.5gHz 4C i7 4710MQ ; 32GB 2.4gHz 8C C2758 ; 32GB ECC
        Vantec 4C USB3 PCIe UGT-PCE430-4C | 8GB AMD SLI R9 M290x |
        SSD  | 850 EVO: 120GB | 1TB ; mSATA: 1TB (2) | 850 Pro: 128GB ; 850 EVO: 1TB
        HDD | Seagate: { ST4000VN000 (8) } Z2 ; { HGST HTS721010A (3) } Z2 |
        FreeNAS 11.2 | { PNY Turbo USB3 32GB (2) } Mirror | Win 10 Pro | ESXi 6.7: Sophos UTM 9.6

        Various Wikis, Scripts, & Configs | Prebuilt OpenSSL Config

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