Complains about TLS inspection, yet fronts their website on the biggest and most widely deployed TLS introspection middle box in the world ...
Why do we all disdain local TLS inspection software yet half the Internet terminates their TLS connection at Cloudflare who are most likely giving direct access to US Intelligence?
It's so much worse as it's infringing on the privacy and security of billions of innocent people whilst inspection software only hurts some annoying enterprise folks.
I wish we all hopped off the Cloudflare bandwagon.
Three of the banks I use have their websites/apps go through CloudFlare. So does the electronic records and messaging system used by my doctor. A lawyer friend uses a secure documents transfer service that is protect by guess who.
Who needs to let CF directly onto their network when they already sit between client and provider for critically-private, privileged communications and records access?
Do you have an alternative, potentially one that's less centralised or private or in bed with three-letter agencies? I ask because my last infra was probed for vulnerabilities hundreds of times per day; putting Cloudflare in front with some blocked countries and their captchas brought the attempted attacks down to a few dozen per month.
> Putting Cloudflare anti-DDoS in front of your website is not the same as breaking all encryption on your internal networks.
You misunderstood, they're complaining about it as a user. If your website uses Cloudflare then our conversation gets terminated by Cloudflare, so they get to see our unencrypted traffic and share it with whomever they want, compromising my privacy.
Which wouldn't be such a problem if it was just an odd website here or there, but Cloudflare is now essentially a TLS middle box for the entire internet with most of the problems that the article complains about, while behind hosted behind Cloudflare.
Given that 50-70% of the critical services I use in my daily life (healthcare, government, banking, insurance) all go through Cloudflare this practically means everything that is important to me as an individual is being actively intercepted by a US entity that falls under NSA's control.
So for all intents and purposes it's equivalent.
My point is: it's very hypocritical that we as industry professionals are complaining about poor cooperates being MITM'd whilst we're perfectly fine enabling the enfringement of fundamental human right to privacy of billions of people by all fronting the shit that we build by Cloudflare in the name of "security".
I find the lack of ethical compass in this regard very disturbing personally
I think it’s misleading to imply hypocrisy considering the reasons listed in the article don’t apply to the scenario of a site being behind Cloudflare.
Tailscale connections don't get terminated by a middle box, it's just end-to-end encrypted Wireguard under the hood. Cloud-hosted control panel is a risk because they could push malicious configuration changes to your clients (ACLs and new nodes if you're not using the lock feature), but they can't do it without leaving a trace like Cloudflare can.
The fact that most tools have completely different ways to allow them to add certificates is the biggest pain. Git, Python and Rust also have large issues. Git doesn't default to "http.schannel". Python (or rather requests, or maybe urllib3) only looks at its own certificate store, and I have no idea how Rust does this (well, I use uv, and it has its own problems - I know about the --use-native-tls flag, but it should be a default at the least).
On Android, macOS/iOS, and Windows, this is a solved problem. Only on the extremely fragmented Linux/Posix runtimes do these problems surface.
Rust's solution is "it depends". You can use OpenSSL (system or statically compiled) or rustls (statically compiled with your own CA roots, system CA roots, or WebPKI CA roots).
I'm afraid that until the *ix operating systems come out with a new POSIX-like definition that stabilises a TLS API, regardless of whether that's the OpenSSL API, the WolfSSL API, or GnuTLS, we'll have to keep hacking around in APIs that need to be compatible with arbitrary TLS configurations. Alternatively, running applications through Waydroid/Wine will work just fine if Linux runtimes can't get their shit together.
Are you sure? It's been a few years, but last I tried Firefox used its own CA store on Windows. I'm pretty sure openjdk uses "<JAVA_HOME>/jre/lib/security/cacerts" instead of the system store too.
It's such a nightmare at my current job as well. Everything always just breaks and needs investigating how to fix.
Even putting aside the MITM and how horrendous that is, the amount of time lost from people dealing with the fallout got to have cost so much time (and money). I can't fathom why anyone competent would want to implement this, let alone not see how much friction and safety issues it causes everywhere.
Yeah, and Java has its nice cacerts file so that should have been easy, but then we were using Bazel which does the "hermetic builds" thing so that had to be told about it separately, and on and on with all the other special-snowflake tools.
It added huge amounts of friction which was one reason I decided to move on from that gig.
I have this similar gripe when it comes to http proxy configuration. It's invisible to you until you are in an execution environment where you are mandated to use the providers proxy configuration.
Some software reads "expected" env variables for it, some has its own config or cli flags, most just doesn't even bother/care about supporting it.
Chiefly because "supporting it" requires a full JavaScript interpreter, and subscribing to changes in "system settings" during the lifetime of your program. Easier just to support http_proxy/https_proxy/no_proxy (and what standard for no_proxy? Does it support CIDR ranges?) or even less flexibility than that.
And many things break in different, exciting ways. For example, we discovered that whilst the JVM can be configured to use system certificate store, that does not apply to websocket connections. So the product seems to be able to connect to the server, but all socket connections bork out with TLS errors.
One thing that has not quite been mentioned in the blog, is how much of the MITM spyware comes from very big and well known „security“ companies.
You know, the ones that really know about security. X-PAN-AUTHCHECK type of security.
The amount of CVEs some of the big firewall companies collect make it seem like it is a competition for the poorest security hygiene.
The real problem we have is compliance theatre where someone in management forces these solutions onto their IT department just so they can check a box on their sheets and shift all responsibilities away.
More and more big customers (especially banks) are requiring this kind of self-inflicted-MITM attack from all their suppliers. Do you want to have customers? Get ready for zscaler!
How do you propose compliance with their exfiltration protection requirements? (And “turn down $ from those customers” is not an answer)
I agree with the sentiment, but I think it's a pretty naive view of the issue. Companies will want all info they can in case some of their workers does something illegal-inappropiate to deflect the blame. That's a much more palpable risk than "local CA certificates being compromised or something like that.
And some of the arguments are just very easily dismissed. You don't want your employer to see you medical records? Why were you browsing them during work hours and using your employers' device in the first place?
TLS inspection can _never_ be implemented in a good way, you will always have cases where it breaks something and most commonly you will see very bad implementations that break most tools (e.g. it is very hard to trust a new CA because each of OS/browser/java/python/... will have their own CA store)
This means devs/users will skip TLS verification ("just make it work") making for a dangerous precedent. Companies want to protect their data? Well, just protect it! Least privilege, data minimization, etc is all good strategies for avoiding data leaking
Security takes many forms, including Availability.
Having branch offices with 100 Mbps (or less!) Internet connections is still common. I’ve worked tickets where the root cause of network problems such as dropped calls ended up being due to bandwidth constraints. Get enough users streaming Spotify and Netflix and it can get in the way of legitimate business needs.
Sure, there’s shaping/qos rules and dns blocking. But the point is that some networks are no place for personal consumption. If an employer wants to use a MITM box to enforce that, so be it.
I think that's a very loose interpretation of Availability in the CIA triad.
This looks a lot like using the MITM hammer to crack every nut.
If this is an actual concern, why not deny personal devices access to the network? Why not restrict the applications that can run on company devices? Or provide a separate connection for personal devices/browsing/streaming?
Why not treat them like people and actually talk to them about the potential impacts. Give people personal responsibility for what they do at work.
Yes, but also it’s not an employer’s job to provide entertainment during work hours on a factory floor where there are machines that can kill you if you’re not careful.
There’s a famous fable where everyone is questioning the theft victim about what they should’ve done and the victim says “doesn’t the thief deserve some words about not stealing?”
Similarly, it’s a corporate network designed and controlled for work purposes. Connecting your personal devices or doing personal work on work devices is already not allowed per policy, but people still do it, so I don’t blame network admins for blocking such connections.
Does GDPR (or similar) establish privacy rights to an employee’s use of a company-owned machine against snooping by their employer? Honest question, I hadn’t heard of that angle. Can employers not install EDR on company-owned machines for EU employees?
(IANAL) I don't think there is a simple response to that, but I guess that given that the employer:
- has established a detailed policy about personal use of corporate devices
- makes a fair attempt to block work unrelated services (hotmail, gmail, netflix)
- ensures the security of the monitored data and deletes it after a reasonable period (such as 6–12 months)
- and uses it only to apply cybersecurity-related measures like virus detection, UNLESS there is a legitimate reason to target a particular employee (legal inquiry, misconduct, etc.)
They can, but the list of "if..." and "it depends..." is much longer and complicated, especially when getting to the part how the obtained information may be used
It has to have a good purpose. Obviously there are a lot of words written about what constitutes a good purpose. Antivirus is probably one. Wanting to intimidate your employees is not. The same thing applies to security cameras.
Privacy laws are about the end-to-end process, not technical implementation. It's not "You can't MITM TLS" - it's more like "You can't spy on your employees". Blocking viruses is not spying on your employees. If you take the logs from the virus blocker and use them to spy on your employees, then you are spying on your employees. (Virus blockers aiming to be sold in the EU would do well not to keep unnecessary logs that could be used to spy on employees.)
Yes.
GDPR covers all handling of PII that a company does. And its sort of default deny, meaning that a company is not allowed to handle (process and/or store) your data UNLESS it has a reason that makes it legal. This is where it becomes more blurry: figuring out if the company has a valid reason. Some are simple, eg. if required by law => valid reason.
GDPR does not care how the data got “in the hands of” the company; the same rules apply.
Another important thing is the pricipals of GDPR. They sort of unline everything. One principal to consider here is that of data minimization. This basically means that IF you have a valid reason to handle an individuals PII, you must limit the data points you handle to exactly what you need and not more.
So - company proxy breaking TLS and logging everything? Well, the company has valid reason to handle some employee data obviously. But if I use my work laptop to access privat health records, then that is very much outside the scope of what my company is allowed handle. And logging (storing) my health data without valid reason is not GDPR compliant.
Could the company fire me for doing private stuff on a work laptop? Yes probably. Does it matter in terms of GDPR? Nope.
Edit: Also, “automatic” or “implicit” consent is not valid. So the company cannot say something like “if you access private info on you work pc the you automatically content to $company handling your data”. All consent must be specific, explicit and retractable
What if your employer says “don’t access your health records on our machine”? If you put private health information in your Twitter bio, Twitter is not obligated to suddenly treat it as if they were collecting private health information. Otherwise every single user-provided field would be maximally radioactive under GDPR.
If the employer says so and I do so anyway then that’s a employment issue. I still have to follow company rules. But the point is that the company needs to delete the collected data as soon as possible. They are still not allowed to store it.
Many programmers tend to treat the legal system as if it was a computer program: if(form.is_public && form.contains(private_health_records)) move(form.owner, get_nearest_jail()); - but this is not how the legal system actually works. Not even in excessively-bureaucratic-and-wording-of-rules-based Germany.
I remember at my first job, the internet stopped working at my workstation. I got on the phone with IT, and the guy said "looks like you don't have our new certificates." I asked why I would need my employer's certificates. He said "because we MITM every connection." I asked if that was even legal, and he said yes it's legal.
At another job I was handling a support ticket where a customer was asking, in so many words, "can I get HTTP headers of requests flowing through my Envoy TLS reverse proxy?" I said that they could terminate TLS at the proxy and redo things that way, but then that wouldn't be a TLS proxy it'd be a MITM or a gateway. They could log the downstream/upstream and duration of connections, but that wouldn't help.
This kind of TLS "man in the middle" tech is so frustrating to deal with, because it ends up breaking things.
For example, I've encountered zscaler setups in the wild which close TLS connections if non-HTTP traffic is encountered. Presumably the traffic inspection fails since there is no HTTP request, and this failure path closes the socket.
It's hard to say whether it's due to the customer's IT dept's config, or zscaler itself -- but as far as the customer is concerned, it's my problem.
It's definitely annoying if you work in enterprise, but on the flip side: the fact that these enterprise requirements exist is the main reason that TLS certificate configurability is possible at all, without which it would be dramatically harder (or impossible) to reverse engineer or do security & privacy research on mobile apps, IoT, etc etc etc.
Enterprise control over company devices and user control over personal devices are not so different.
A few apps do use certificate pinning nowadays, which creates similar problems, but saying "you can never add your own MitM TLS cert" is not far from certificate pinning everything everywhere all the time. Good luck creating a new home assistant integration for your smart airfryer when you can't read any of the traffic from its app.
Imo: let's make it easier! Standardize TLS configuration for all tools, make easy cert configuration of devices a legal requirement (any smart device sold with hardcoded CA certificates is a device with a fixed end date, where the CA certs expire and it becomes a brick), guarantee user control over their own TLS trust, and provide good tools to check exactly who you're trusting (and expose that clearly to users). Not really practical of course (and opens all sorts of risky games with nation state interception as well) but there are upsides here as well.
What changed my mind to be in favor of TLS inspection at work environments was seeing what kind of highly confidential stuff employees might be copy-pasting to random websites, LLM assistants, cloud-based "desktop applications" and such against the approved use policies of each of these tools without giving it a second thought.
TLS inspection products can intercept the paste transaction before the data leaves the company network, hitting the user with a "No you didn't! Shame on you!"-banner and notify the admins how a user just tried to paste hundreds of customers' personal information and credit card details into some snooping website, or into otherwise allowed LLM chat which still is not allowed to be used with confidential information.
There can even be automations to lock the user/device out immediately if something like this is going on, be it the user or some undetected malware in the user's device attempting the intercepted action. Being able to do these kinds of very specifically targeted interceptions can prevent potentially huge disasters from happening while still allowing users more freedom in taking advantage of the huge variety of productivity tools available these days. No need to choose between completely blocking all previously unseen tools or living in fear of disastrous leaks when there are fine-grained possibilities to control what kind of information can be fed to the tools and from where.
There are plenty of organizations out there where it is completely justified to enforce such limitations and monitoring in company devices. Policies can forbid personal use entirely where it is deemed necessary and legal to do so. Of course the policies and the associated enforced monitoring needs to be clearly communicated and there needs to be carefully curated configurations to control where and how TLS is or isn't intercepted so employee privacy laws and regulations aren't breached either.
While eps, edr, etc. solutions have their role in security and some of the products can be used for "TLS inspection" within the localhost already, doing the inspection in separate network appliance brings benefits such as (but not limited to) not needing to care if the client operating system is supported by the eps product or if the eps is functioning correctly, offloading the "heavy lifting" and policy enforcement to the appliances and ensuring that only actual real egress connections to specific services are inspected.
That’s vastly more failure prone (crowdstrike crashes workstations) and abuse prone (kernel code has the highest privilege level) than processing network traffic at the network/TLS level.
In practice you don't actually need kernel code on a bunch of platforms for this, e.g. NETransparentProxyManager on MacOS. This is not necessarily an endorsement, just worth not mixing in unrelated issues.
> Consider this - what is the likelihood of every certificate authority on the Internet having their private keys compromised simultaneously? I’d wager that’s almost at the whatever is the statistics equivalent of the Planck length level of probability.
It doesn't matter if every certificate authority is compromised or just one. One is all that is needed to sign certificates for all websites.
That was what I was thinking of (but worded it badly in the middle of my rant!)
If I wanted to intercept all your traffic to any external endpoint without detection I would have to compromise the exact CA that signed your certificates each time, because it would be a clear sign of concern if e.g. Comodo started issuing certificates for Google. Although of course as long as a CA is in my trust bundle then the traffic could be intercepted, it's just that the CT logs would make it very clear that something bad had happened.
The whole point of the logs is that they're tamper-evident. If you think the certificate you've seen wasn't logged you can show proof. If you think the logs tell you something different from everybody else you can prove that too.
It is striking that we don't see that. We reliably see people saying "obviously" the Mossad or the NSA are snooping but they haven't shown any evidence that there's tampering
> We reliably see people saying "obviously" the Mossad or the NSA are snooping but they haven't shown any evidence that there's tampering
Why would they use the one approach that leaves a verifiable trace? That'd be foolish.
- They can intercept everything in the comfort of Cloudflare's datacenters
- They can "politely" ask Cloudflare, AWS, Google cloud, etc. to send them a copy of the private keys for certificates that have already been issued
- They either have a backdoor, or have the capability to add a backdoor in the hardware that generates those keys in the first place, should more convenient forms of access fail.
Our cyber team have installed zscaler on most people's laptop, and somewhere in the fabric of the office internet connection.[1]
For those that don't know, its a MITM proxy with certificates so that it can inspect and unroll TLS traffic.
ostensibly its there to stop data exfiltration, as we've had a number of incidents where people have stolen data and sent it to competitors. (our c-suite don't have as much cyber shit installed, despite them being the ones that are both targets more, and broken the rules more....)
Now, I don't like zscaler, and I can sorta see the point of it. But.
Our cyber team is not a centre of technical excellence. They somehow managed to configure zscaler to send out the certs for a random property company, when people were trying to sign into our VPN.
this broke loads of shit and made my team (infra) look bad. The worrying part is they still haven't accepted that serving a random property company's website cert instead of our own/AWS's cert is monster fuckup, and that we need to understand _why_ that happened before trying anything again.
[1] this makes automatic pen testing interesting because everything we scan has vulnerabilities for NFS/CIFS, FTP and TCP dns.
Security team in most of the corporates is just a bunch of checklists markers, so for zscaler, crowdstrike or whatever they’re doing for compliance and/or certification and you can’t say no to it because it’s the company policy and who know better than “security” team?
Lame on user machines, but sometimes needed in a server environment. Easier to detect if someone is hauling off with your database as that will be the one you can’t see what’s going on. Of course, solve one problem and introduce three more.
> Consider this - what is the likelihood of every certificate authority on the Internet having their private keys compromised simultaneously?
Considering that CloudFlare has managed to MitM a huge part of the internet, I'd say that probability is not just non-zero, but greater than by a worrying margin.
I work for a school. My traffic is not MITM'd, but the kids' traffic is, because we don't want them using their school-issued laptops to play games or go shopping, and you can't adequately block stuff if it's all encrypted.
I'm hoping this doesn't apply to things like Fiddler, because without the ability to see what's actually coming over the wire with a https connection, things can be a nightmare to debug sometimes
a company, I worked for, had their own endpoint which you can easily introduce in windows, unfortunately every other tls connection which does not use the windows certificate store breaks because of that, so maven, npm et al won't work
I largely agree with the author. When our SOC wanted to implement TLS inspection I blocked it. Mostly because we not nearly at the security level for this, but also because it just fucks with so many things.
That said, we are not a business dealing with highly sensitive data or legal responsibilities surrounding data loss prevention.
If you are a business like that, say a bank or a hospital, you want to be able to block patient / customer data leaving your systems. You can do this by setting up a regex for a known format like patient numbers or bank account numbers.
This requires TLS inspection obviously.
Though this makes it harder to steal this data, not impossible.
It does however allow the C-suite to say they did everything they could to prevent it.
Netskope and the other DLP tools at my last gig would completely lock up my network connection for around 30 seconds every hour or two while maxing out 100% of a core. Fun times. The issue was still there a year after I first encountered it so I have grave doubts about the competence of those vendors.
On the other hand I am sympathetic to the needs of big regulated orgs to show they're doing something to avoid data loss. It's a painful situation.
personally i'm happy that i can MITM my docker when it wants to pull gigs of images the 1000th time upstream and just serve them from a local OCI cache server instead.
Honestly, the author is spot on about the normalisation problem. I've watched this play out at multiple organisations. You implement TLS inspection, spend ages getting certs deployed, and within six months `curl -k` is in half your runbooks because "it's just the corporate proxy again".
He's also absolutely right about the architectural problems too, single points of failure, performance bottlenecks, and the complexity in cloud-native environments.
That said, it can be a genuinely valuable layer in your security arsenal when done properly. I've seen it catch real threats, such as malware C2 comms, credential phishing, data exfiltration attempts. These aren't theoretical; they happen daily. Combined with decent threat intelligence feeds and behavioural analytics, it does provide visibility that's hard to replicate elsewhere.
But, and this is a massive but, you can't half-arse it. If you're going to do TLS inspection, you need to actually commit:
Treat that internal CA like it's the crown jewels. HSMs, strict access controls, proper rotation schedules, full-chain and sensible life-span. The point about concentrated risk is bang on, you've turned thousands of distributed CA keys into one single target. So act like it. Run it like a proper CA with proper key signing ceremonies and all the safeguards etc.
Actually invest in proper cert distribution. Configuration management (Ansible/Salt/whatever), golden container base images with the CA bundle baked in, MDM for endpoints, cloud-init for VMs. If you can't reliably push a cert bundle to your entire estate, you've got bigger problems than TLS inspection.
Train people properly on what errors are expected vs "drop everything and call security". Document the exceptions. Make reporting easy. Actually investigate when someone raises a TLS error they don't recognise. For dev's, it needs to just work without them even thinking about it. Then they don't need to work around it, ever. If they need to, the system is busted.
Scope it ruthlessly. Not everything needs to go through the proxy. Developer workstations with proper EDR? Maybe exclude them. Production services with cert pinning? Route direct. Every blanket "intercept everything" policy I've seen has been a disaster. Particularly for end-users doing personal banking, medical stuff, therapy sessions, do you really want IT/Sec seeing that?
Use it alongside modern defences. ie EDR, Zero Trust, behavioural analytics, CASB. It should be one layer in defence-in-depth, not your entire security strategy.
Build observability, you need metrics on what's being inspected, what's bypassing, failure rates, performance impact. If you can't measure it, you can't manage it.
But Yeah, the core criticism stands though, even done well, it's a massive operational burden and it actively undermines trust in TLS. The failure modes are particularly insidious because you're training people to ignore the very warnings that are meant to protect them.
The real question isn't "TLS inspection: yes or no?" It's: "Do we have the organisational maturity, resources, and commitment to do this properly?" If you're not in a regulated industry or don't have dedicated security teams and mature infrastructure practices, just don't bother. But if you must do it, and plenty of organisations genuinely must, then do it properly or don't do it at all.
I agree with the sentiment, but this part is complete bullshit:
> what is the likelihood of every certificate authority on the Internet having their private keys compromised simultaneously
Who cares? It's not like all CAs would have to be breached, just one. CA certs are not scoped, so the moment one CA gets breached, we're all fucked. CT helps, but AFAIK it's still not enforced everywhere yet
There's no actual market pressure to be secure, so nobody cares about threat modeling, cost/benefit of security solutions, etc. The only pressure in case of breach is political blame that you need to deflect. The point of a cybersecurity solution is to be there, remind you it is there, and allow you to deflect blame in case of disaster. Whether it actually increases security is merely a bonus side-effect.
zScaler is a load of shit, especially with some of its absolutely dumb policies like “malicious TLDs”.
Because the Framework laptop site at frame.work is malicious, of course.
God, I love CURLing crap from my workstation and not getting the files I needed but instead a bunch of mangled HTML telling me zScaler was going to scan what I was going to download.
Bonus points that it puts me in the wrong country because I’m closer to Montreal than any American locations so half the time I’m stuck in French Canadian on the web from my New York office.
Triple bonus points that I’m required to test speed at client sites and zScaler completely mangles our presentable results.
Quadruple bonus points that I put in "because I feel like it" into every elevation request I make on my corporate machine and our "cyber team" has literally never looked at elevation reports to ask what the hell I'm doing...
Got acquired by a Fortune 500 and recieved new laptop. First hour I'm seeing TLS errors everywhere except the browser.
They'd half-baked their internal CA rollout, so wasn't trusted properly.
By day two I started validating their setup. The CA literally had a typo in the company name, not a great sign.
A quick check with badssl.com showed that any self-signed(!) cert was being transparently MITM'ed and re-signed by their trusted corporate cert. Took them 40 days to fix it.
Another fun side-effect of this is that devs will just turned off TLS verification, so their codebase is full of `curl -k`, `verify_mode = VERIFY_NONE`, `ServerCertificateValidationCallback = () => true`, ... Exactly the thing you want to see at a big fintech company /s
Hey, allowing your employees to have secure connection to websites shows up in red in some Excel spreadsheet. We can't have Excel spreadsheets showing red in fintech. /s
Complains about TLS inspection, yet fronts their website on the biggest and most widely deployed TLS introspection middle box in the world ...
Why do we all disdain local TLS inspection software yet half the Internet terminates their TLS connection at Cloudflare who are most likely giving direct access to US Intelligence?
It's so much worse as it's infringing on the privacy and security of billions of innocent people whilst inspection software only hurts some annoying enterprise folks.
I wish we all hopped off the Cloudflare bandwagon.
Three of the banks I use have their websites/apps go through CloudFlare. So does the electronic records and messaging system used by my doctor. A lawyer friend uses a secure documents transfer service that is protect by guess who.
Who needs to let CF directly onto their network when they already sit between client and provider for critically-private, privileged communications and records access?
NSAaaS and people even pay for it.
Do you have an alternative, potentially one that's less centralised or private or in bed with three-letter agencies? I ask because my last infra was probed for vulnerabilities hundreds of times per day; putting Cloudflare in front with some blocked countries and their captchas brought the attempted attacks down to a few dozen per month.
I'm not sure if you're serious but in case you are (or other people):
TLS inspection is for EVERYTHING in your network, not just your publicly reachable URLs.
Putting Cloudflare anti-DDoS in front of your website is not the same as breaking all encryption on your internal networks.
Google can already see the content of this site since it's hosted... on the internet.
> Putting Cloudflare anti-DDoS in front of your website is not the same as breaking all encryption on your internal networks.
You misunderstood, they're complaining about it as a user. If your website uses Cloudflare then our conversation gets terminated by Cloudflare, so they get to see our unencrypted traffic and share it with whomever they want, compromising my privacy.
Which wouldn't be such a problem if it was just an odd website here or there, but Cloudflare is now essentially a TLS middle box for the entire internet with most of the problems that the article complains about, while behind hosted behind Cloudflare.
Given that 50-70% of the critical services I use in my daily life (healthcare, government, banking, insurance) all go through Cloudflare this practically means everything that is important to me as an individual is being actively intercepted by a US entity that falls under NSA's control.
So for all intents and purposes it's equivalent.
My point is: it's very hypocritical that we as industry professionals are complaining about poor cooperates being MITM'd whilst we're perfectly fine enabling the enfringement of fundamental human right to privacy of billions of people by all fronting the shit that we build by Cloudflare in the name of "security".
I find the lack of ethical compass in this regard very disturbing personally
...do you send private messages using services hosted on publicly reachable URLs?
I think it’s misleading to imply hypocrisy considering the reasons listed in the article don’t apply to the scenario of a site being behind Cloudflare.
I wish so too, same for all the self-hosters using tailscale...
Tailscale connections don't get terminated by a middle box, it's just end-to-end encrypted Wireguard under the hood. Cloud-hosted control panel is a risk because they could push malicious configuration changes to your clients (ACLs and new nodes if you're not using the lock feature), but they can't do it without leaving a trace like Cloudflare can.
Tailscale cannot passively observe traffic.
They could inject malicious keys into your config but would be hard to mask the evidence of that.
Would it be hard? I thought the point of tailscale was not having to manage or concern yourself with key distribution.
Lookup the Tailnet Lock feature.
These are not the same thing, the parent is confused..
The fact that most tools have completely different ways to allow them to add certificates is the biggest pain. Git, Python and Rust also have large issues. Git doesn't default to "http.schannel". Python (or rather requests, or maybe urllib3) only looks at its own certificate store, and I have no idea how Rust does this (well, I use uv, and it has its own problems - I know about the --use-native-tls flag, but it should be a default at the least).
On Android, macOS/iOS, and Windows, this is a solved problem. Only on the extremely fragmented Linux/Posix runtimes do these problems surface.
Rust's solution is "it depends". You can use OpenSSL (system or statically compiled) or rustls (statically compiled with your own CA roots, system CA roots, or WebPKI CA roots).
I'm afraid that until the *ix operating systems come out with a new POSIX-like definition that stabilises a TLS API, regardless of whether that's the OpenSSL API, the WolfSSL API, or GnuTLS, we'll have to keep hacking around in APIs that need to be compatible with arbitrary TLS configurations. Alternatively, running applications through Waydroid/Wine will work just fine if Linux runtimes can't get their shit together.
> Windows, this is a solved problem.
Are you sure? It's been a few years, but last I tried Firefox used its own CA store on Windows. I'm pretty sure openjdk uses "<JAVA_HOME>/jre/lib/security/cacerts" instead of the system store too.
It's such a nightmare at my current job as well. Everything always just breaks and needs investigating how to fix.
Even putting aside the MITM and how horrendous that is, the amount of time lost from people dealing with the fallout got to have cost so much time (and money). I can't fathom why anyone competent would want to implement this, let alone not see how much friction and safety issues it causes everywhere.
> I can't fathom why anyone competent would want to implement this
Compliance. Big financial orgs. and the like must show that they are doing something about "data loss" and this, sadly, is the easiest way to do that.
There's money in it if you can show them a better way.
Yeah, and Java has its nice cacerts file so that should have been easy, but then we were using Bazel which does the "hermetic builds" thing so that had to be told about it separately, and on and on with all the other special-snowflake tools.
It added huge amounts of friction which was one reason I decided to move on from that gig.
I have this similar gripe when it comes to http proxy configuration. It's invisible to you until you are in an execution environment where you are mandated to use the providers proxy configuration.
Some software reads "expected" env variables for it, some has its own config or cli flags, most just doesn't even bother/care about supporting it.
Chiefly because "supporting it" requires a full JavaScript interpreter, and subscribing to changes in "system settings" during the lifetime of your program. Easier just to support http_proxy/https_proxy/no_proxy (and what standard for no_proxy? Does it support CIDR ranges?) or even less flexibility than that.
And many things break in different, exciting ways. For example, we discovered that whilst the JVM can be configured to use system certificate store, that does not apply to websocket connections. So the product seems to be able to connect to the server, but all socket connections bork out with TLS errors.
Fun!
And so many of those products deliver broken chains, and your client needs to download more certificates transparently ( https://systemweakness.com/the-hidden-jvm-flag-that-instantl... )
Double the fun!
One thing that has not quite been mentioned in the blog, is how much of the MITM spyware comes from very big and well known „security“ companies.
You know, the ones that really know about security. X-PAN-AUTHCHECK type of security.
The amount of CVEs some of the big firewall companies collect make it seem like it is a competition for the poorest security hygiene.
The real problem we have is compliance theatre where someone in management forces these solutions onto their IT department just so they can check a box on their sheets and shift all responsibilities away.
As a sysadmin I also hate this. Instead, I do block stuff based on DNS requests and I also block any other DNS provider as well as malicious IPs.
At this point in time, Microsoft is the bigger enemy here - some of their policies are just insane and none of this MITM will help [0][1]
[0] https://www.microsoft.com/en-us/microsoft-365/roadmap?id=490...
[1] https://techcommunity.microsoft.com/blog/microsoft365copilot...
More and more big customers (especially banks) are requiring this kind of self-inflicted-MITM attack from all their suppliers. Do you want to have customers? Get ready for zscaler!
How do you propose compliance with their exfiltration protection requirements? (And “turn down $ from those customers” is not an answer)
I agree with the sentiment, but I think it's a pretty naive view of the issue. Companies will want all info they can in case some of their workers does something illegal-inappropiate to deflect the blame. That's a much more palpable risk than "local CA certificates being compromised or something like that.
And some of the arguments are just very easily dismissed. You don't want your employer to see you medical records? Why were you browsing them during work hours and using your employers' device in the first place?
TLS inspection can _never_ be implemented in a good way, you will always have cases where it breaks something and most commonly you will see very bad implementations that break most tools (e.g. it is very hard to trust a new CA because each of OS/browser/java/python/... will have their own CA store)
This means devs/users will skip TLS verification ("just make it work") making for a dangerous precedent. Companies want to protect their data? Well, just protect it! Least privilege, data minimization, etc is all good strategies for avoiding data leaking
I’m all for privacy of individuals, but work network is not a public internet either.
A solution is required to limit the network to work related activities and also inspect server communications for unusual patterns.
In one example someone’s phone was using the work WiFi to “accidentally” stream 20 GB of Netflix a day.
What's the security risk of someone streaming Netflix?
There are better ways to ensure people are getting their work done that don't involve spying on them in the name of "security".
What’s wrong with watching Netflix at work instead of working? That’s not for me to say, but I understand employers not wanting to allow it.
Security takes many forms, including Availability.
Having branch offices with 100 Mbps (or less!) Internet connections is still common. I’ve worked tickets where the root cause of network problems such as dropped calls ended up being due to bandwidth constraints. Get enough users streaming Spotify and Netflix and it can get in the way of legitimate business needs.
Sure, there’s shaping/qos rules and dns blocking. But the point is that some networks are no place for personal consumption. If an employer wants to use a MITM box to enforce that, so be it.
I think that's a very loose interpretation of Availability in the CIA triad.
This looks a lot like using the MITM hammer to crack every nut.
If this is an actual concern, why not deny personal devices access to the network? Why not restrict the applications that can run on company devices? Or provide a separate connection for personal devices/browsing/streaming?
Why not treat them like people and actually talk to them about the potential impacts. Give people personal responsibility for what they do at work.
Yes, but also it’s not an employer’s job to provide entertainment during work hours on a factory floor where there are machines that can kill you if you’re not careful.
There’s a famous fable where everyone is questioning the theft victim about what they should’ve done and the victim says “doesn’t the thief deserve some words about not stealing?”
Similarly, it’s a corporate network designed and controlled for work purposes. Connecting your personal devices or doing personal work on work devices is already not allowed per policy, but people still do it, so I don’t blame network admins for blocking such connections.
In Europe they prefer not to go to jail for privacy violations. It turns out most of these "communist" regulations are actually pretty great.
Does GDPR (or similar) establish privacy rights to an employee’s use of a company-owned machine against snooping by their employer? Honest question, I hadn’t heard of that angle. Can employers not install EDR on company-owned machines for EU employees?
(IANAL) I don't think there is a simple response to that, but I guess that given that the employer:
- has established a detailed policy about personal use of corporate devices
- makes a fair attempt to block work unrelated services (hotmail, gmail, netflix)
- ensures the security of the monitored data and deletes it after a reasonable period (such as 6–12 months)
- and uses it only to apply cybersecurity-related measures like virus detection, UNLESS there is a legitimate reason to target a particular employee (legal inquiry, misconduct, etc.)
I would say that it's very much doable.
Edit: More info from the Dutch regulator https://english.ncsc.nl/publications/factsheets/2019/juni/01...
Yes, at least in the Netherlands it is generally accepted that employees can use your device personally, too.
Using a device owned by your company to access your personal GMail account does NOT void your legal right to privacy.
So does nobody in Europe use an EDR or intercepting proxy since GDPR went into force?
I have found a definite answer from the Dutch Protection Agency (although it could be out of date).
https://english.ncsc.nl/binaries/ncsc-en/documenten/factshee...
They can, but the list of "if..." and "it depends..." is much longer and complicated, especially when getting to the part how the obtained information may be used
It has to have a good purpose. Obviously there are a lot of words written about what constitutes a good purpose. Antivirus is probably one. Wanting to intimidate your employees is not. The same thing applies to security cameras.
Privacy laws are about the end-to-end process, not technical implementation. It's not "You can't MITM TLS" - it's more like "You can't spy on your employees". Blocking viruses is not spying on your employees. If you take the logs from the virus blocker and use them to spy on your employees, then you are spying on your employees. (Virus blockers aiming to be sold in the EU would do well not to keep unnecessary logs that could be used to spy on employees.)
Yes. GDPR covers all handling of PII that a company does. And its sort of default deny, meaning that a company is not allowed to handle (process and/or store) your data UNLESS it has a reason that makes it legal. This is where it becomes more blurry: figuring out if the company has a valid reason. Some are simple, eg. if required by law => valid reason.
GDPR does not care how the data got “in the hands of” the company; the same rules apply. Another important thing is the pricipals of GDPR. They sort of unline everything. One principal to consider here is that of data minimization. This basically means that IF you have a valid reason to handle an individuals PII, you must limit the data points you handle to exactly what you need and not more.
So - company proxy breaking TLS and logging everything? Well, the company has valid reason to handle some employee data obviously. But if I use my work laptop to access privat health records, then that is very much outside the scope of what my company is allowed handle. And logging (storing) my health data without valid reason is not GDPR compliant.
Could the company fire me for doing private stuff on a work laptop? Yes probably. Does it matter in terms of GDPR? Nope.
Edit: Also, “automatic” or “implicit” consent is not valid. So the company cannot say something like “if you access private info on you work pc the you automatically content to $company handling your data”. All consent must be specific, explicit and retractable
What if your employer says “don’t access your health records on our machine”? If you put private health information in your Twitter bio, Twitter is not obligated to suddenly treat it as if they were collecting private health information. Otherwise every single user-provided field would be maximally radioactive under GDPR.
If the employer says so and I do so anyway then that’s a employment issue. I still have to follow company rules. But the point is that the company needs to delete the collected data as soon as possible. They are still not allowed to store it.
Many programmers tend to treat the legal system as if it was a computer program: if(form.is_public && form.contains(private_health_records)) move(form.owner, get_nearest_jail()); - but this is not how the legal system actually works. Not even in excessively-bureaucratic-and-wording-of-rules-based Germany.
I remember at my first job, the internet stopped working at my workstation. I got on the phone with IT, and the guy said "looks like you don't have our new certificates." I asked why I would need my employer's certificates. He said "because we MITM every connection." I asked if that was even legal, and he said yes it's legal.
At another job I was handling a support ticket where a customer was asking, in so many words, "can I get HTTP headers of requests flowing through my Envoy TLS reverse proxy?" I said that they could terminate TLS at the proxy and redo things that way, but then that wouldn't be a TLS proxy it'd be a MITM or a gateway. They could log the downstream/upstream and duration of connections, but that wouldn't help.
The title should say "Stop inspecting TLS", the current title reads like the TLS standard or technology is modified in a way to not work properly.
For what it's worth, I knew exactly what this was going to be about before I clicked.
"If you use my (private) network you follow my rules"
And I find it hard to argue with that.
I've been using a VPN habitually on my phone and my (personal) laptop for a decade now. Work, home, travel. Doesn't matter. It's always on.
How do you find your typical daily battery life with it always on?
I’ve tried this in the past and had to revert as I found it made a noticeable difference in my day-to-day.
Curious to hear the experience of others.
Was it OpenVPN that you tried in the past? Wireguard seems much better
This kind of TLS "man in the middle" tech is so frustrating to deal with, because it ends up breaking things.
For example, I've encountered zscaler setups in the wild which close TLS connections if non-HTTP traffic is encountered. Presumably the traffic inspection fails since there is no HTTP request, and this failure path closes the socket.
It's hard to say whether it's due to the customer's IT dept's config, or zscaler itself -- but as far as the customer is concerned, it's my problem.
It's definitely annoying if you work in enterprise, but on the flip side: the fact that these enterprise requirements exist is the main reason that TLS certificate configurability is possible at all, without which it would be dramatically harder (or impossible) to reverse engineer or do security & privacy research on mobile apps, IoT, etc etc etc.
Enterprise control over company devices and user control over personal devices are not so different.
A few apps do use certificate pinning nowadays, which creates similar problems, but saying "you can never add your own MitM TLS cert" is not far from certificate pinning everything everywhere all the time. Good luck creating a new home assistant integration for your smart airfryer when you can't read any of the traffic from its app.
Imo: let's make it easier! Standardize TLS configuration for all tools, make easy cert configuration of devices a legal requirement (any smart device sold with hardcoded CA certificates is a device with a fixed end date, where the CA certs expire and it becomes a brick), guarantee user control over their own TLS trust, and provide good tools to check exactly who you're trusting (and expose that clearly to users). Not really practical of course (and opens all sorts of risky games with nation state interception as well) but there are upsides here as well.
What changed my mind to be in favor of TLS inspection at work environments was seeing what kind of highly confidential stuff employees might be copy-pasting to random websites, LLM assistants, cloud-based "desktop applications" and such against the approved use policies of each of these tools without giving it a second thought.
TLS inspection products can intercept the paste transaction before the data leaves the company network, hitting the user with a "No you didn't! Shame on you!"-banner and notify the admins how a user just tried to paste hundreds of customers' personal information and credit card details into some snooping website, or into otherwise allowed LLM chat which still is not allowed to be used with confidential information.
There can even be automations to lock the user/device out immediately if something like this is going on, be it the user or some undetected malware in the user's device attempting the intercepted action. Being able to do these kinds of very specifically targeted interceptions can prevent potentially huge disasters from happening while still allowing users more freedom in taking advantage of the huge variety of productivity tools available these days. No need to choose between completely blocking all previously unseen tools or living in fear of disastrous leaks when there are fine-grained possibilities to control what kind of information can be fed to the tools and from where.
There are plenty of organizations out there where it is completely justified to enforce such limitations and monitoring in company devices. Policies can forbid personal use entirely where it is deemed necessary and legal to do so. Of course the policies and the associated enforced monitoring needs to be clearly communicated and there needs to be carefully curated configurations to control where and how TLS is or isn't intercepted so employee privacy laws and regulations aren't breached either.
So deploy end point security, which sits in the kernel and can thus access the unencrypted communication
While eps, edr, etc. solutions have their role in security and some of the products can be used for "TLS inspection" within the localhost already, doing the inspection in separate network appliance brings benefits such as (but not limited to) not needing to care if the client operating system is supported by the eps product or if the eps is functioning correctly, offloading the "heavy lifting" and policy enforcement to the appliances and ensuring that only actual real egress connections to specific services are inspected.
That’s vastly more failure prone (crowdstrike crashes workstations) and abuse prone (kernel code has the highest privilege level) than processing network traffic at the network/TLS level.
In practice you don't actually need kernel code on a bunch of platforms for this, e.g. NETransparentProxyManager on MacOS. This is not necessarily an endorsement, just worth not mixing in unrelated issues.
Aren’t most TLS implementations still using things like OpenSSL in userspace? How would the kernel get access to the request?
A process with kernel level permissions can patch into userspace process an intercept calls. For example https://github.com/SebastienWae/sslsnoop
> Consider this - what is the likelihood of every certificate authority on the Internet having their private keys compromised simultaneously? I’d wager that’s almost at the whatever is the statistics equivalent of the Planck length level of probability.
It doesn't matter if every certificate authority is compromised or just one. One is all that is needed to sign certificates for all websites.
Author here, hi! Was just venting last night, but that's a very good point, I'll update it later with your correction :)
You should make it about CT logs. I believe you need to compromise at least three of them.
That was what I was thinking of (but worded it badly in the middle of my rant!)
If I wanted to intercept all your traffic to any external endpoint without detection I would have to compromise the exact CA that signed your certificates each time, because it would be a clear sign of concern if e.g. Comodo started issuing certificates for Google. Although of course as long as a CA is in my trust bundle then the traffic could be intercepted, it's just that the CT logs would make it very clear that something bad had happened.
The whole point of the logs is that they're tamper-evident. If you think the certificate you've seen wasn't logged you can show proof. If you think the logs tell you something different from everybody else you can prove that too.
It is striking that we don't see that. We reliably see people saying "obviously" the Mossad or the NSA are snooping but they haven't shown any evidence that there's tampering
> We reliably see people saying "obviously" the Mossad or the NSA are snooping but they haven't shown any evidence that there's tampering
Why would they use the one approach that leaves a verifiable trace? That'd be foolish.
- They can intercept everything in the comfort of Cloudflare's datacenters
- They can "politely" ask Cloudflare, AWS, Google cloud, etc. to send them a copy of the private keys for certificates that have already been issued
- They either have a backdoor, or have the capability to add a backdoor in the hardware that generates those keys in the first place, should more convenient forms of access fail.
> It is striking that we don't see that
It probably just means they are asking the providers to hand over the data, no need to perform active attacks.
This is only relevant for active MITM attacks.
Our cyber team have installed zscaler on most people's laptop, and somewhere in the fabric of the office internet connection.[1]
For those that don't know, its a MITM proxy with certificates so that it can inspect and unroll TLS traffic.
ostensibly its there to stop data exfiltration, as we've had a number of incidents where people have stolen data and sent it to competitors. (our c-suite don't have as much cyber shit installed, despite them being the ones that are both targets more, and broken the rules more....)
Now, I don't like zscaler, and I can sorta see the point of it. But.
Our cyber team is not a centre of technical excellence. They somehow managed to configure zscaler to send out the certs for a random property company, when people were trying to sign into our VPN.
this broke loads of shit and made my team (infra) look bad. The worrying part is they still haven't accepted that serving a random property company's website cert instead of our own/AWS's cert is monster fuckup, and that we need to understand _why_ that happened before trying anything again.
[1] this makes automatic pen testing interesting because everything we scan has vulnerabilities for NFS/CIFS, FTP and TCP dns.
Security team in most of the corporates is just a bunch of checklists markers, so for zscaler, crowdstrike or whatever they’re doing for compliance and/or certification and you can’t say no to it because it’s the company policy and who know better than “security” team?
This is 100% true.
Lame on user machines, but sometimes needed in a server environment. Easier to detect if someone is hauling off with your database as that will be the one you can’t see what’s going on. Of course, solve one problem and introduce three more.
This is why I don't use the computers at work for anything not work related. They've been spying on us for at least 10 years.
> Consider this - what is the likelihood of every certificate authority on the Internet having their private keys compromised simultaneously?
Considering that CloudFlare has managed to MitM a huge part of the internet, I'd say that probability is not just non-zero, but greater than by a worrying margin.
But I need to see what they are googling! /sarcasm
I work for a school. My traffic is not MITM'd, but the kids' traffic is, because we don't want them using their school-issued laptops to play games or go shopping, and you can't adequately block stuff if it's all encrypted.
Whitelists instead of blacklists?
I'm pretty sure we'd still need to break TLS. Domain-level just isn't granular enough.
I can't imagine the headache as a school when parents come yelling "why did you allow my child on site XXX?!"
I'm hoping this doesn't apply to things like Fiddler, because without the ability to see what's actually coming over the wire with a https connection, things can be a nightmare to debug sometimes
a company, I worked for, had their own endpoint which you can easily introduce in windows, unfortunately every other tls connection which does not use the windows certificate store breaks because of that, so maven, npm et al won't work
I largely agree with the author. When our SOC wanted to implement TLS inspection I blocked it. Mostly because we not nearly at the security level for this, but also because it just fucks with so many things.
That said, we are not a business dealing with highly sensitive data or legal responsibilities surrounding data loss prevention.
If you are a business like that, say a bank or a hospital, you want to be able to block patient / customer data leaving your systems. You can do this by setting up a regex for a known format like patient numbers or bank account numbers.
This requires TLS inspection obviously.
Though this makes it harder to steal this data, not impossible.
It does however allow the C-suite to say they did everything they could to prevent it.
Oh and the software (Netskope) was only able to decrypt our traffic in the cloud.
Lmao not in a million fucking years will I upload our data to an American company in fucking plaintext.
Netskope and the other DLP tools at my last gig would completely lock up my network connection for around 30 seconds every hour or two while maxing out 100% of a core. Fun times. The issue was still there a year after I first encountered it so I have grave doubts about the competence of those vendors.
On the other hand I am sympathetic to the needs of big regulated orgs to show they're doing something to avoid data loss. It's a painful situation.
personally i'm happy that i can MITM my docker when it wants to pull gigs of images the 1000th time upstream and just serve them from a local OCI cache server instead.
You don't need to MITM docker for this, you can just configure your containerd or equivalent backend properly.
Honestly, the author is spot on about the normalisation problem. I've watched this play out at multiple organisations. You implement TLS inspection, spend ages getting certs deployed, and within six months `curl -k` is in half your runbooks because "it's just the corporate proxy again".
He's also absolutely right about the architectural problems too, single points of failure, performance bottlenecks, and the complexity in cloud-native environments.
That said, it can be a genuinely valuable layer in your security arsenal when done properly. I've seen it catch real threats, such as malware C2 comms, credential phishing, data exfiltration attempts. These aren't theoretical; they happen daily. Combined with decent threat intelligence feeds and behavioural analytics, it does provide visibility that's hard to replicate elsewhere.
But, and this is a massive but, you can't half-arse it. If you're going to do TLS inspection, you need to actually commit:
Treat that internal CA like it's the crown jewels. HSMs, strict access controls, proper rotation schedules, full-chain and sensible life-span. The point about concentrated risk is bang on, you've turned thousands of distributed CA keys into one single target. So act like it. Run it like a proper CA with proper key signing ceremonies and all the safeguards etc.
Actually invest in proper cert distribution. Configuration management (Ansible/Salt/whatever), golden container base images with the CA bundle baked in, MDM for endpoints, cloud-init for VMs. If you can't reliably push a cert bundle to your entire estate, you've got bigger problems than TLS inspection.
Train people properly on what errors are expected vs "drop everything and call security". Document the exceptions. Make reporting easy. Actually investigate when someone raises a TLS error they don't recognise. For dev's, it needs to just work without them even thinking about it. Then they don't need to work around it, ever. If they need to, the system is busted.
Scope it ruthlessly. Not everything needs to go through the proxy. Developer workstations with proper EDR? Maybe exclude them. Production services with cert pinning? Route direct. Every blanket "intercept everything" policy I've seen has been a disaster. Particularly for end-users doing personal banking, medical stuff, therapy sessions, do you really want IT/Sec seeing that?
Use it alongside modern defences. ie EDR, Zero Trust, behavioural analytics, CASB. It should be one layer in defence-in-depth, not your entire security strategy.
Build observability, you need metrics on what's being inspected, what's bypassing, failure rates, performance impact. If you can't measure it, you can't manage it.
But Yeah, the core criticism stands though, even done well, it's a massive operational burden and it actively undermines trust in TLS. The failure modes are particularly insidious because you're training people to ignore the very warnings that are meant to protect them.
The real question isn't "TLS inspection: yes or no?" It's: "Do we have the organisational maturity, resources, and commitment to do this properly?" If you're not in a regulated industry or don't have dedicated security teams and mature infrastructure practices, just don't bother. But if you must do it, and plenty of organisations genuinely must, then do it properly or don't do it at all.
Hallelujah!
But I have to say, big regulated orgs are often not competent to do things this (the right) way but don't have the option of not doing it at all.
I agree with the sentiment, but this part is complete bullshit:
> what is the likelihood of every certificate authority on the Internet having their private keys compromised simultaneously
Who cares? It's not like all CAs would have to be breached, just one. CA certs are not scoped, so the moment one CA gets breached, we're all fucked. CT helps, but AFAIK it's still not enforced everywhere yet
Companies know that it's important to have Cybersecurity™. A vendor shows up with shiny brochures, and company is happy to purchase Cybersecurity™.
Now they don't have to worry about it anymore, they bought a product that sits in the corner and delivers Cybersecurity™
You've perfectly summarized the entire industry.
There's no actual market pressure to be secure, so nobody cares about threat modeling, cost/benefit of security solutions, etc. The only pressure in case of breach is political blame that you need to deflect. The point of a cybersecurity solution is to be there, remind you it is there, and allow you to deflect blame in case of disaster. Whether it actually increases security is merely a bonus side-effect.
zScaler is a load of shit, especially with some of its absolutely dumb policies like “malicious TLDs”.
Because the Framework laptop site at frame.work is malicious, of course.
God, I love CURLing crap from my workstation and not getting the files I needed but instead a bunch of mangled HTML telling me zScaler was going to scan what I was going to download.
Bonus points that it puts me in the wrong country because I’m closer to Montreal than any American locations so half the time I’m stuck in French Canadian on the web from my New York office.
Triple bonus points that I’m required to test speed at client sites and zScaler completely mangles our presentable results.
Quadruple bonus points that I put in "because I feel like it" into every elevation request I make on my corporate machine and our "cyber team" has literally never looked at elevation reports to ask what the hell I'm doing...
Got acquired by a Fortune 500 and recieved new laptop. First hour I'm seeing TLS errors everywhere except the browser. They'd half-baked their internal CA rollout, so wasn't trusted properly.
By day two I started validating their setup. The CA literally had a typo in the company name, not a great sign.
A quick check with badssl.com showed that any self-signed(!) cert was being transparently MITM'ed and re-signed by their trusted corporate cert. Took them 40 days to fix it.
Another fun side-effect of this is that devs will just turned off TLS verification, so their codebase is full of `curl -k`, `verify_mode = VERIFY_NONE`, `ServerCertificateValidationCallback = () => true`, ... Exactly the thing you want to see at a big fintech company /s
Hey, allowing your employees to have secure connection to websites shows up in red in some Excel spreadsheet. We can't have Excel spreadsheets showing red in fintech. /s