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for the recent time i have been actively using PPTP to externally connect to my home network. This is going great as i can easily browse my local NAS's content.

But it seems like PPTP has some serious security flaws. The question is: Do i have to worry about someone entering my home network unauthorized?

Important: I use the VPN only in secure locations (so i don't have to worry about MITM attacks), and the password used are completely random and about 50 characters long)

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What "Serious security flaws" are you referring to? –  Scott Chamberlain Jul 18 '11 at 21:47
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migrated from stackoverflow.com Jul 18 '11 at 20:59

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If you are referring to the Wikipedia page talking about the vulnerabilities of MSCHAP for the "security issues" the fact that you are using a password that is "completely random and about 50 characters long" will mitigate the issues due to MSCHAP-v2 is only vulnerable to dictionary attacks. One thing you can do is make sure your VPN will not fall back to MSCHAP-v1 if v2 does not work.

You should be fine, you are much more in danger of a key-logger or someone shoulder surfing your password then someone doing a MITM attach and figuring out your password.

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