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BlueCoat and other proxies hang up during TLS 1.3

bugs.chromium.org

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Re: BlueCoat and other proxies hang up during TLS 1.3

#61
post #40

The title was editorialized. TLS 1.3 is a working draft and Chromium is just doing field trial with it. A few days ago there were other issues with this causing Chromium to stop working on *.google.com so it's not just about middle-boxes. https://bugs.debian.org/cgi-bin/bugreport.cgi?bug=855434 https://bugs.chromium.org/p/chromium/issues/detail?id=693943

Not necessarily just a field trial. AFAIK it was bundled with a recent ChromeOS update, causing logon to fail when MITM'd

Re: BlueCoat and other proxies hang up during TLS 1.3

#62

Note that this happens even when using a BlueCoat proxy in non-MITM mode. BlueCoat tries to "analyze" TLS connections, and rejects anything it doesn't understand. This exact issue occurred with TLS 1.2 back when BlueCoat only understood 1.1/1.0. In this case, it doesn't sound like they're reverting it because of overall breakage, but rather because it breaks the tool that would otherwise be used to control TLS 1.3 tr…

This exact issue occurred with TLS 1.2 back when BlueCoat only understood 1.1/1.0. Good grief! From David Benjamin's final comment: Note these issues are always bugs in the middlebox products. TLS version negotiation is backwards compatible, so a correctly-implemented TLS-terminating proxy should not require changes to work in a TLS-1.3-capable ecosystem. It can simply speak TLS 1.2 at both client proxy and proxy ser…

Bluecoat is extremely widely used in some fields. They were in the news a while back when it was discovered that Syria (before the civil war) was censoring their internet access using Bluecoat devices (allegedly unauthorized by Bluecoat)[1]

[1] https://en.wikipedia.org/wiki/Blue_Coat_Systems#Use_by_repre...

Re: BlueCoat and other proxies hang up during TLS 1.3

#64

Earlier quoted context omitted.

This is something the TLS spec authors have prepared against with GREASE. The idea is the client adds some junk version information to its list of supported protocols. To quote: "Correct server implementations will ignore these values and interoperate. Servers that do not tolerate unknown values will fail to interoperate with existing clients, revealing the mistake before it is widespread." https://tools.ietf.org/htm…

This dosent really seem to solve anything, everyone now ignores the enumerated GREASE values as they are reserved upfront, and will continue to cause failures with other extended values. yay?

This at least means that the developer is aware that these parts of the spec are extensible, and by explicitly ignoring the GREASE values are explicitly choosing to potentially have a broken application in the future. This is a different class of problems than developers who weren't aware certain fields were extensible.

Re: BlueCoat and other proxies hang up during TLS 1.3

#65
post #40

The title was editorialized. TLS 1.3 is a working draft and Chromium is just doing field trial with it. A few days ago there were other issues with this causing Chromium to stop working on *.google.com so it's not just about middle-boxes. https://bugs.debian.org/cgi-bin/bugreport.cgi?bug=855434 https://bugs.chromium.org/p/chromium/issues/detail?id=693943

While there was a secondary issue with the deployment regarding unofficial builds/derivatives, the field trial was primarily rolled back due to the number of affected customers due to the middle-box issues in their enterprise/edu networks.

Re: BlueCoat and other proxies hang up during TLS 1.3

#67

Earlier quoted context omitted.

At my workplace where we have to do tls inspection for regulatory purposes we provide an internet-only wifi network for employee personal use where we don't intercept TLS. This network is fully isolated from the corporate network and corporate devices join a different, more monitored network. I believe this strikes the best balance between regulatory compliance and employee privacy. People can still use personal emai…

> but no corporate data can be moved en mass off company servers. How so? 1. Connect to Corp Wifi 2. git clone companyapp.git 3. Connect to Employee Personal Wifi 4. Email tgz'ed companyapp ?

When connecting a corporate device to any non-corporate network (including the employee wifi) you can't go anywhere until the vpn is connected. The vpn routes you through all the same inspection points as being on premise.

Re: BlueCoat and other proxies hang up during TLS 1.3

#68
post #54

Earlier quoted context omitted.

Without an SSL MITM, Intrusion Detection Systems (IDS's) are much less effective. If you're using your company's network, then they have every right to monitor all of the activity on it. They're trying to protect trade secrets, future plans, customer data, employee records, etc. from attackers who would use that information to do harm to the company, its customers, and its employees. If you don't want your employer t…

> If you're using your company's network, then they have every right to monitor all of the activity on it. It isn't a question of whether they're allowed to do it, it's a question of whether they should do it. It's ineffective against insider exfiltration of data unless you're also doing body cavity searches for USB sticks, and if you're at that point then the sensitive network should not be connected to the internet…

>It's ineffective against insider exfiltration of data unless you're also doing body cavity searches for USB sticks, and if you're at that point then the sensitive network should not be connected to the internet at all.

We opted to disable usb mass storage since cavity searches seemed a little much

Re: BlueCoat and other proxies hang up during TLS 1.3

#70
post #59

Earlier quoted context omitted.

Without an SSL MITM, Intrusion Detection Systems (IDS's) are much less effective. If you're using your company's network, then they have every right to monitor all of the activity on it. They're trying to protect trade secrets, future plans, customer data, employee records, etc. from attackers who would use that information to do harm to the company, its customers, and its employees. If you don't want your employer t…

If you're using your company's network, then they have every right to monitor all of the activity on it. This is tantamount to steaming open and resealing the envelopes of all physical mail. Have some god damn ethics, I'd sooner quit than snoop traffic in this manner.

All MITM proxies I know require an enterprise CA trusted by the end-point. If that CA is on your machine the endpoint is probably owned by your employer. It is legal in most jurisdictions for your employer to monitor the usage of resources they have provided, be it computer or network.

I would never trust a company device, or company network, with anything I consider sensitive. Use your own device and keep it on cellular.

Also though I don't like it, employers in the US do have the right to open mail addressed to you personally if delivered to the office.

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