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Then the first thing you need to do as part of setting up a VPN program is to figure out a software update process/policy that lets you push updates within hour

by geofft 7y ago

Then the first thing you need to do as part of setting up a VPN program is to figure out a software update process/policy that lets you push updates within hours and ensures you always do have the ability to patch (i.e., that you either know where you're getting updated binaries from for every client OS that connects or you know how to build them yourself). If you build a system where updates are part of the process, it works - take a look at say video games (which have far fewer people caring about their security than, like, the average corporate VPN), where having people on the latest version is just part of the expectations, and it works fine. Otherwise, what's your plan for a Heartbleed-style scenario? Wait months for everyone to upgrade?

Spivak 7y ago
I feel like you’re assuming that I will have total control over every device that wants to connect which just isn’t realistic. I mean the baseline case of a VPN that your employees use by both their work computers, personal computers, and phones. I can’t forcibly update all of those and politically I can’t cut people off because the truth is that being able to get work done is more important to the business. Then I have to deal with vendor provided devices that are slow to receive updates or possibly will never receive updates ever. Again, I can’t just turn them off much as I would like to. No room in the budget to buy replacements. The old one is working fiiiine. And then I have to deal with partners and oh boy I can’t even pretend to understand why they’re using an out of warranty Cisco box from 5 years ago but we make too much money through them to raise a fuss. So that’s what I got. Everything I own gets migrated immediately. The help desk goes after everyone who doesn’t know how to update their apps. And we make special exceptions for random junk that can’t ever upgrade but is too valuable to turn off. So yeah, you pretty much have to wait months for the stragglers but everyone who can upgrade does so immediately. I’m sure lots of people here can tell lots of horror stories about turning off TLS 1.1.
- geofft 7y ago
  > I mean the baseline case of a VPN that your employees use by both their work computers, personal computers, and phones. I can’t forcibly update all of those and politically I can’t cut people off because the truth is that being able to get work done is more important to the business. Then your priority isn't security. Which isn't necessarily a criticism, it's just a statement of what your business's priorities are. Don't hide behind "well, IPsec supports all sorts of security knobs that can make it approximately as good as Wireguard, if you squint hard enough this is actually the more secure thing." Just say, no, security is not the top priority for this application, and we're going to design our systems around connectivity/reliability instead of security. You could decide security goes elsewhere the design, if you want, and add additional internal isolation once someone's on the VPN to avoid infected endpoints from messing with your corporate network. You could also just decide that a VPN isn't what you want, you want cloud services and BeyondCorp and the assumption of mostly-untrusted endpoints. (Then your users don't have to install VPN software at all, they just need a web browser.) Or for your partners with the out-of-warranty Cisco box - stick a firewall in front of them on your side and also arrange to use authenticated/encrypted application protocols as if you were connecting over the public network. Or say, security and reliability are both priorities but cost isn't, we're buying everyone a work-managed laptop and a work-managed phone. (Or, if you really want to connect from your personal device, you can use a fully-patched one, and if you don't have one, the company will buy you one. Or whatever.) But you cannot say that your priority is security and your priority is allowing unpatched devices to connect. (I don't know anyone with a horror story about turning off TLS 1.1 who originally turned it on because they wanted secure connections. All of those people supported TLS 1.2 and the good ciphers before anyone forced them to. I know people with horror stories because they turned on TLS because they needed to check some regulator's checkbox.)
  - Spivak 7y ago
    > Don't hide behind "well, IPsec supports all sorts of security knobs that can make it approximately as good as Wireguard," That's not really what I was getting at. I guess it would be something like "in situations where the priority is connectivity/reliability you will have better overall security with an IPSec deployment than a WireGuard one." But otherwise I think your assessment is absolutely correct and we do employ pretty much all of those tricks. Although the horror stories about TLS 1.1 is finding out just how many of your customers are running ancient clients that don't support TLS 1.2.

by geofft 7y ago

Spivak 7y ago

I feel like you’re assuming that I will have total control over every device that wants to connect which just isn’t realistic. I mean the baseline case of a VPN that your employees use by both their work computers, personal computers, and phones. I can’t forcibly update all of those and politically I can’t cut people off because the truth is that being able to get work done is more important to the business. Then I have to deal with vendor provided devices that are slow to receive updates or possibly will never receive updates ever. Again, I can’t just turn them off much as I would like to. No room in the budget to buy replacements. The old one is working fiiiine. And then I have to deal with partners and oh boy I can’t even pretend to understand why they’re using an out of warranty Cisco box from 5 years ago but we make too much money through them to raise a fuss. So that’s what I got. Everything I own gets migrated immediately. The help desk goes after everyone who doesn’t know how to update their apps. And we make special exceptions for random junk that can’t ever upgrade but is too valuable to turn off. So yeah, you pretty much have to wait months for the stragglers but everyone who can upgrade does so immediately. I’m sure lots of people here can tell lots of horror stories about turning off TLS 1.1.

geofft 7y ago
> I mean the baseline case of a VPN that your employees use by both their work computers, personal computers, and phones. I can’t forcibly update all of those and politically I can’t cut people off because the truth is that being able to get work done is more important to the business. Then your priority isn't security. Which isn't necessarily a criticism, it's just a statement of what your business's priorities are. Don't hide behind "well, IPsec supports all sorts of security knobs that can make it approximately as good as Wireguard, if you squint hard enough this is actually the more secure thing." Just say, no, security is not the top priority for this application, and we're going to design our systems around connectivity/reliability instead of security. You could decide security goes elsewhere the design, if you want, and add additional internal isolation once someone's on the VPN to avoid infected endpoints from messing with your corporate network. You could also just decide that a VPN isn't what you want, you want cloud services and BeyondCorp and the assumption of mostly-untrusted endpoints. (Then your users don't have to install VPN software at all, they just need a web browser.) Or for your partners with the out-of-warranty Cisco box - stick a firewall in front of them on your side and also arrange to use authenticated/encrypted application protocols as if you were connecting over the public network. Or say, security and reliability are both priorities but cost isn't, we're buying everyone a work-managed laptop and a work-managed phone. (Or, if you really want to connect from your personal device, you can use a fully-patched one, and if you don't have one, the company will buy you one. Or whatever.) But you cannot say that your priority is security and your priority is allowing unpatched devices to connect. (I don't know anyone with a horror story about turning off TLS 1.1 who originally turned it on because they wanted secure connections. All of those people supported TLS 1.2 and the good ciphers before anyone forced them to. I know people with horror stories because they turned on TLS because they needed to check some regulator's checkbox.)
- Spivak 7y ago
  > Don't hide behind "well, IPsec supports all sorts of security knobs that can make it approximately as good as Wireguard," That's not really what I was getting at. I guess it would be something like "in situations where the priority is connectivity/reliability you will have better overall security with an IPSec deployment than a WireGuard one." But otherwise I think your assessment is absolutely correct and we do employ pretty much all of those tricks. Although the horror stories about TLS 1.1 is finding out just how many of your customers are running ancient clients that don't support TLS 1.2.