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i have a HSS VPN client on my laptop. Whenever i press the connect button, a secure tunnel is set up between me and the VPN server via my TAP adapter which got IP address 10.X.X.X. Once i'm connected, my public IP assigned my local ISP is replaced with the one those VPN servers'.

Even though, one of the servers' IP address was assigned to mine(offering the identity preservation that time) i wonder if ISP can prevent me from establishing a connection via TAP adapter. (i mean the stage of pressing 'the connect' button).

i mean, just before receiving those servers' IP address, could ISP block me to do that? could they identify where im attempting to connect?

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ISP's usually do not prevent their users from connecting to certain IP addresses, so this is not possible.

I would say the most sure method to know that your IP is changed to the VPN one is checking the "Network Connections" window for your connection status to the VPN. If it says connected, then surely your ISP is not preventing from connecting from it.

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They actually do, see the blockage of piracy sites, or various Great Firewalls. However, an ISP could only block the VPN server itself, not specific connections over a VPN. – grawity Aug 13 '12 at 16:40

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