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Questions tagged [sstp]

Secure Socket Tunneling Protocol (SSTP) is a form of VPN tunnel that provides a mechanism to transport PPP or L2TP traffic through an SSL 3.0 channel

SSTP is only available in Windows since version Windows Vista SP1, in RouterOS, and in SEIL since its firmware version 3.50. It is fully integrated with the RRAS architecture in these operating systems, allowing its use with Winlogon or smart card authentication, remote access policies and the Windows VPN client.

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SSTP VPN Windows Server 2008 - Clients can't access Internet Through the VPN

I have setup a SSTP VPN connect and it is assigning the local IP address to the client, e.g. 192.168.0.10. The server has two NICs, private and public. The private is on a 10.180.x.x IP address and the public has the public IP address. When I…
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IKEv2 certificate error but SSTP successfully connects Windows 10 pro / Windows Server 2019

I'm using Windows server 2019 (installed roles: AD DC, CA, DHCP, DNS, IIS, VPN). my client is Windows 10 pro. before installing the Online responder role and having a CRL server, IkEv2 was working, but after installing and configuring that role (in…
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SSTP VPN connection fails after updating / removing an IIS certificate

After I removed / updated an IIS certificate, I am unable to maintain an SSTP VPN connection with the server. As far as I recall the certificate was NOT used for authentication. Users authenticate with a username and password. The VPN connection is…
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MS SSTP Server with multiple certificates / hostnames

We currently have an SSTP server (running on Windows Server 2008 R2 but it is being migrated to Windows Server 2016). At the moment, the server is configured using a wildcard certificate for one of our domains, lets call it *.olddomain.com. As you…
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Redirect SSTP traffic from Ubuntu Apache2 server to internal Windows Server

So this weekend i have been working on migrating my apache2 server to a docker container which i have no issues with. I currently have a windows server with SSTP and Exchange 2016 both using port 443 for traffic. The idea is to have incoming 443…
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SSTP VPN on Windows Server 2016 works in LAN but not from WAN

I was setting up SSTP VPN on Windows Server 2016 at home using this tutorial. This works using a LAN client with Windows 10. The eventlog on the client shows: The user xxx has established a connection with VPN SSTP using the device VPN4-1.…
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Can I set up a Windows SSTP VPN service without exposing the webserver?

I am trying to set up a SSTP VPN service in Windows 2016. I don't want to advertise to the world that my network exists let alone that I have a running webserver, but because the SSTP service runs over HTTPS in IIS it does exactly this. Any casual…
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How to create site-to-site VPN from CentOS Server to Windows Server

For a small business: at one site is windows 2012 server, (with ssl certificate), already running as a SSTP VPN Server. At a remote site, is a live-to-public CentOS webserver running CFS. Requirement: To establish a permanent and reliable VPN tunnel…
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Cannot connect to SSTP VPN Error 20227

I have a working PPTP VPN on Windows Server 2008 and I can connect to this PPTP VPN on a Windows 10 notebook with an AD-User. But when I am trying to switch to SSTP on my Windows Server by importing the certificate and set the "SSL Certificate…
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SSTP: Certificate issue

So I'm building an SSTP VPN. I get the following error when trying to connect to the VPN: A certificate chain processed, but terminated in a root certificate which is not trusted by the trust provider. To generate the certificate I used selfssl.exe…
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Is RRAS SSTP VPN using publicly signed certificate a bad idea?

Most guides for deploying SSTP on RRAS recommend setting up a private CA using AD CS, with all the necessary steps that come with that to issue a server authentication certificate and have it trusted by the clients. From what I've read, it's also…
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Windows Server: VPN clients cannot see LAN clients

I'm trying to set up a server running Windows Server 2012 R2 to host VPN (RRAS). I have gotten VPN connections to work with certificates (SSTP). Now I need the VPN clients to be able to see LAN clients, and LAN clients to see VPN clients. I haven't…
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Deploying SSTP VPN on Windows 2012 - How to route packets to other servers?

I've finally managed to deploy an SSTP VPN between my Windows 2012 (non R2) server and Windows 7 client. It's amazing how much easier it work with a real certificate and avoiding the self-signed debacle. Anyway, my client can ping the VPN server and…
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Can connect through SSTP but not PPTP?

I have a window server 2008 r2 box behind a a Netgear AC1750 router. I've set up RRAS for a VPN and can successfully connect using SSTP, but if I try to connect to the VPN using PPTP I get a timeout error. I don't have an error message on my…
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Windows Server 2008 R2 creating a multi-year client certificate using the IIS certsrv page while deploying SSTP VPN

I am trying to follow instructions on Technet about deploying a Standard (non-enterprise) SSTP based VPN) that were originally written for Server 2008, but I am using Server 2008 R2, I have gotten as far as the part where it asks you to create a…
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