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As I understand it, SSL/TLS is used when we visit a website using https. However, using this method only encrypts the data and not the IP address of the website we're requesting.

If you use a VPN secured with SSL/TLS, then this WILL prevent somebody (who is sniffing) from seeing the IP addresses of your website request?

Also, with the VPN-SSL I presume because DNS is on the application layer (along with http) the VPN would also prevent sniffers from discovering which website youre visiting from checking your DNS requests?

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Yes, everything inside the tunnel is protected. Observers can see the address of the tunnel endpoint.

However the tunnel ends somewhere and from there your TCP connection has to reach a webserver, the destination of that part of the journey can be observed. Someone might be able to correlate the two sets of activity.

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I understand a VPN-SSL is easier to configure than IPSec: What if I wanted to rent a VPN-SSL Server to be one end of my tunnel and the other end would be my client. Would I need software on my client, or would I use my browser to connect to my "rented server" and then browse the internet via that, a bit like those proxy websites? – Trevor Jan 10 at 20:25
Moreover, a third-party cookie set during a non-VPN-protected browser session can also be accessed inside a VPN-protected session, essentially exposing your identity... VPN is not a panacea, it is only a part of a bigger solution (separate browser, etc.). – haimg Jan 10 at 20:29
Trevor: Depends on the OS...Windows has no native SSL-VPN support whereas Linux does through OpenVPN. I believe you're still confusing a true VPN versus an SSL-capable proxy. In your case you probably would be better off with a proxy. – Garrett Jan 11 at 0:23
@gman, to be honest i havent seen a good explanation of how SSL/https is different to SSL-VPN?? When I read SSL-VPN documentation they just gloss over the 'VPN' bit?? look at this: cisco.com/en/US/prod/collateral/iosswrel/ps6537/ps6586/ps6657/… – Trevor Jan 11 at 0:39
This question was just recently asked and answered here on SU: superuser.com/questions/373196/ssl-tls-vs-ssl-tls-vpn/… – Garrett Jan 11 at 6:01
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