Matthew Garrett

Here's an article from a French anarchist describing how his (encrypted) laptop was seized after he was arrested, and material from the encrypted partition has since been entered as evidence against him. His encryption password was supposedly greater than 20 characters and included a mixture of cases, numbers, and punctuation, so in the absence of any sort of opsec failures this implies that even relatively complex passwords can now be brute forced, and we should be transitioning to even more secure passphrases.

Or does it? Let's go into what LUKS is doing in the first place. The actual data is typically encrypted with AES, an extremely popular and well-tested encryption algorithm. AES has no known major weaknesses and is not considered to be practically brute-forceable - at least, assuming you have a random key. Unfortunately it's not really practical to ask a user to type in 128 bits of binary every time they want to unlock their drive, so another approach has to be taken.

This is handled using something called a "key derivation function", or KDF. A KDF is a function that takes some input (in this case the user's password) and generates a key. As an extremely simple example, think of MD5 - it takes an input and generates a 128-bit output, so we could simply MD5 the user's password and use the output as an AES key. While this could technically be considered a KDF, it would be an extremely bad one! MD5s can be calculated extremely quickly, so someone attempting to brute-force a disk encryption key could simply generate the MD5 of every plausible password (probably on a lot of machines in parallel, likely using GPUs) and test each of them to see whether it decrypts the drive.

(things are actually slightly more complicated than this - your password is used to generate a key that is then used to encrypt and decrypt the actual encryption key. This is necessary in order to allow you to change your password without having to re-encrypt the entire drive - instead you simply re-encrypt the encryption key with the new password-derived key. This also allows you to have multiple passwords or unlock mechanisms per drive)

Good KDFs reduce this risk by being what's technically referred to as "expensive". Rather than performing one simple calculation to turn a password into a key, they perform a lot of calculations. The number of calculations performed is generally configurable, in order to let you trade off between the amount of security (the number of calculations you'll force an attacker to perform when attempting to generate a key from a potential password) and performance (the amount of time you're willing to wait for your laptop to generate the key after you type in your password so it can actually boot). But, obviously, this tradeoff changes over time - defaults that made sense 10 years ago are not necessarily good defaults now. If you set up your encrypted partition some time ago, the number of calculations required may no longer be considered up to scratch.

And, well, some of these assumptions are kind of bad in the first place! Just making things computationally expensive doesn't help a lot if your adversary has the ability to test a large number of passwords in parallel. GPUs are extremely good at performing the sort of calculations that KDFs generally use, so an attacker can "just" get a whole pile of GPUs and throw them at the problem. KDFs that are computationally expensive don't do a great deal to protect against this. However, there's another axis of expense that can be considered - memory. If the KDF algorithm requires a significant amount of RAM, the degree to which it can be performed in parallel on a GPU is massively reduced. A Geforce 4090 may have 16,384 execution units, but if each password attempt requires 1GB of RAM and the card only has 24GB on board, the attacker is restricted to running 24 attempts in parallel.

So, in these days of attackers with access to a pile of GPUs, a purely computationally expensive KDF is just not a good choice. And, unfortunately, the subject of this story was almost certainly using one of those. Ubuntu 18.04 used the LUKS1 header format, and the only KDF supported in this format is PBKDF2. This is not a memory expensive KDF, and so is vulnerable to GPU-based attacks. But even so, systems using the LUKS2 header format used to default to argon2i, again not a memory expensive KDFwhich is memory strong, but not designed to be resistant to GPU attack (thanks to the comments pointing out my misunderstanding here). New versions default to argon2id, which is. You want to be using argon2id.

What makes this worse is that distributions generally don't update this in any way. If you installed your system and it gave you pbkdf2 as your KDF, you're probably still using pbkdf2 even if you've upgraded to a system that would use argon2id on a fresh install. Thankfully, this can all be fixed-up in place. But note that if anything goes wrong here you could lose access to all your encrypted data, so before doing anything make sure it's all backed up (and figure out how to keep said backup secure so you don't just have your data seized that way).

First, make sure you're running as up-to-date a version of your distribution as possible. Having tools that support the LUKS2 format doesn't mean that your distribution has all of that integrated, and old distribution versions may allow you to update your LUKS setup without actually supporting booting from it. Also, if you're using an encrypted /boot, stop now - very recent versions of grub2 support LUKS2, but they don't support argon2id, and this will render your system unbootable.

Next, figure out which device under /dev corresponds to your encrypted partition. Run

lsblk

and look for entries that have a type of "crypt". The device above that in the tree is the actual encrypted device. Record that name, and run

sudo cryptsetup luksHeaderBackup /dev/whatever --header-backup-file /tmp/luksheader

and copy that to a USB stick or something. If something goes wrong here you'll be able to boot a live image and run

sudo cryptsetup luksHeaderRestore /dev/whatever --header-backup-file luksheader

to restore it.

(Edit to add: Once everything is working, delete this backup! It contains the old weak key, and someone with it can potentially use that to brute force your disk encryption key using the old KDF even if you've updated the on-disk KDF.)

Next, run

sudo cryptsetup luksDump /dev/whatever

and look for the Version: line. If it's version 1, you need to update the header to LUKS2. Run

sudo cryptsetup convert /dev/whatever --type luks2

and follow the prompts. Make sure your system still boots, and if not go back and restore the backup of your header. Assuming everything is ok at this point, run

sudo cryptsetup luksDump /dev/whatever

again and look for the PBKDF: line in each keyslot (pay attention only to the keyslots, ignore any references to pbkdf2 that come after the Digests: line). If the PBKDF is either "pbkdf2" or "argon2i" you should convert to argon2id. Run the following:

sudo cryptsetup luksConvertKey /dev/whatever --pbkdf argon2id

and follow the prompts. If you have multiple passwords associated with your drive you'll have multiple keyslots, and you'll need to repeat this for each password.

Distributions! You should really be handling this sort of thing on upgrade. People who installed their systems with your encryption defaults several years ago are now much less secure than people who perform a fresh install today. Please please please do something about this.

Github accidentally committed their SSH RSA private key to a repository, and now a bunch of people's infrastructure is broken because it needs to be updated to trust the new key. This is obviously bad, but what's frustrating is that there's no inherent need for it to be - almost all the technological components needed to both reduce the initial risk and to make the transition seamless already exist.

But first, let's talk about what actually happened here. You're probably used to the idea of TLS certificates from using browsers. Every website that supports TLS has an asymmetric pair of keys divided into a public key and a private key. When you contact the website, it gives you a certificate that contains the public key, and your browser then performs a series of cryptographic operations against it to (a) verify that the remote site possesses the private key (which prevents someone just copying the certificate to another system and pretending to be the legitimate site), and (b) generate an ephemeral encryption key that's used to actually encrypt the traffic between your browser and the site. But what stops an attacker from simply giving you a fake certificate that contains their public key? The certificate is itself signed by a certificate authority (CA), and your browser is configured to trust a preconfigured set of CAs. CAs will not give someone a signed certificate unless they prove they have legitimate ownership of the site in question, so (in theory) an attacker will never be able to obtain a fake certificate for a legitimate site.

This infrastructure is used for pretty much every protocol that can use TLS, including things like SMTP and IMAP. But SSH doesn't use TLS, and doesn't participate in any of this infrastructure. Instead, SSH tends to take a "Trust on First Use" (TOFU) model - the first time you ssh into a server, you receive a prompt asking you whether you trust its public key, and then you probably hit the "Yes" button and get on with your life. This works fine up until the point where the key changes, and SSH suddenly starts complaining that there's a mismatch and something awful could be happening (like someone intercepting your traffic and directing it to their own server with their own keys). Users are then supposed to verify whether this change is legitimate, and if so remove the old keys and add the new ones. This is tedious and risks users just saying "Yes" again, and if it happens too often an attacker can simply redirect target users to their own server and through sheer fatigue at dealing with this crap the user will probably trust the malicious server.

Why not certificates? OpenSSH actually does support certificates, but not in the way you might expect. There's a custom format that's significantly less complicated than the X509 certificate format used in TLS. Basically, an SSH certificate just contains a public key, a list of hostnames it's good for, and a signature from a CA. There's no pre-existing set of trusted CAs, so anyone could generate a certificate that claims it's valid for, say, github.com. This isn't really a problem, though, because right now nothing pays attention to SSH host certificates unless there's some manual configuration.

(It's actually possible to glue the general PKI infrastructure into SSH certificates. Please do not do this)

So let's look at what happened in the Github case. The first question is "How could the private key have been somewhere that could be committed to a repository in the first place?". I have no unique insight into what happened at Github, so this is conjecture, but I'm reasonably confident in it. Github deals with a large number of transactions per second. Github.com is not a single computer - it's a large number of machines. All of those need to have access to the same private key, because otherwise git would complain that the private key had changed whenever it connected to a machine with a different private key (the alternative would be to use a different IP address for every frontend server, but that would instead force users to repeatedly accept additional keys every time they connect to a new IP address). Something needs to be responsible for deploying that private key to new systems as they're brought up, which means there's ample opportunity for it to accidentally end up in the wrong place.

Now, best practices suggest that this should be avoided by simply placing the private key in a hardware module that performs the cryptographic operations, ensuring that nobody can ever get at the private key. The problem faced here is that HSMs typically aren't going to be fast enough to handle the number of requests per second that Github deals with. This can be avoided by using something like a Nitro Enclave, but you're still going to need a bunch of these in different geographic locales because otherwise your front ends are still going to be limited by the need to talk to an enclave on the other side of the planet, and now you're still having to deal with distributing the private key to a bunch of systems.

What if we could have the best of both worlds - the performance of private keys that just happily live on the servers, and the security of private keys that live in HSMs? Unsurprisingly, we can! The SSH private key could be deployed to every front end server, but every minute it could call out to an HSM-backed service and request a new SSH host certificate signed by a private key in the HSM. If clients are configured to trust the key that's signing the certificates, then it doesn't matter what the private key on the servers is - the client will see that there's a valid certificate and will trust the key, even if it changes. Restricting the validity of the certificate to a small window of time means that if a key is compromised an attacker can't do much with it - the moment you become aware of that you stop signing new certificates, and once all the existing ones expire the old private key becomes useless. You roll out a new private key with new certificates signed by the same CA and clients just carry on trusting it without any manual involvement.

Why don't we have this already? The main problem is that client tooling just doesn't handle this well. OpenSSH has no way to do TOFU for CAs, just the keys themselves. This means there's no way to do a git clone ssh://git@github.com/whatever and get a prompt asking you to trust Github's CA. Instead, you need to add a @cert-authority github.com (key) line to your known_hosts file by hand, and since approximately nobody's going to do that there's only marginal benefit in going to the effort to implement this infrastructure. The most important thing we can do to improve the security of the SSH ecosystem is to make it easier to use certificates, and that means improving the behaviour of the clients.

It should be noted that certificates aren't the only approach to handling key migration. OpenSSH supports a protocol for key rotation, basically by allowing the server to provide a set of multiple trusted keys that the client can cache, and then invalidating old ones. Unfortunately this still requires that the "new" private keys be deployed in the same way as the old ones, so any screwup that results in one private key being leaked may well also result in the additional keys being leaked. I prefer the certificate approach.

Finally, I've seen a couple of people imply that the blame here should be attached to whoever or whatever caused the private key to be committed to a repository in the first place. This is a terrible take. Humans will make mistakes, and your systems should be resilient against that. There's no individual at fault here - there's a series of design decisions that made it possible for a bad outcome to occur, and in a better universe they wouldn't have been necessary. Let's work on building that better universe.

After my previous efforts, I wrote up a PKCS#11 module of my own that had no odd restrictions about using non-RSA keys and I tested it. And things looked much better - ssh successfully obtained the key, negotiated with the server to determine that it was present in authorized_keys, and then went to actually do the key verification step. At which point things went wrong - the Sign() method in my PKCS#11 module was never called, and a strange
debug1: identity_sign: sshkey_sign: error in libcrypto
sign_and_send_pubkey: signing failed for ECDSA "testkey": error in libcrypto"
error appeared in the ssh output. Odd. libcrypto was originally part of OpenSSL, but Apple ship the LibreSSL fork. Apple don't include the LibreSSL source in their public source repo, but do include OpenSSH. I grabbed the OpenSSH source and jumped through a whole bunch of hoops to make it build (it uses the macosx.internal SDK, which isn't publicly available, so I had to cobble together a bunch of headers from various places), and also installed upstream LibreSSL with a version number matching what Apple shipped. And everything worked - I logged into the server using a hardware-backed key.

Was the difference in OpenSSH or in LibreSSL? Telling my OpenSSH to use the system libcrypto resulted in the same failure, so it seemed pretty clear this was an issue with the Apple version of the library. The way all this works is that when OpenSSH has a challenge to sign, it calls ECDSA_do_sign(). This then calls ECDSA_do_sign_ex(), which in turn follows a function pointer to the actual signature method. By default this is a software implementation that expects to have the private key available, but you can also register your own callback that will be used instead. The OpenSSH PKCS#11 code does this by calling EC_KEY_set_method(), and as a result calling ECDSA_do_sign() ends up calling back into the PKCS#11 code that then calls into the module that communicates with the hardware and everything works.

Except it doesn't under macOS. Running under a debugger and setting a breakpoint on EC_do_sign(), I saw that we went down a code path with a function called ECDSA_do_sign_new(). This doesn't appear in any of the public source code, so seems to be an Apple-specific patch. I pushed Apple's libcrypto into Ghidra and looked at ECDSA_do_sign() and found something that approximates this:

nid = EC_GROUP_get_curve_name(curve);
if (nid == NID_X9_62_prime256v1) {
  return ECDSA_do_sign_new(dgst,dgst_len,eckey);
}
return ECDSA_do_sign_ex(dgst,dgst_len,NULL,NULL,eckey);

What this means is that if you ask ECDSA_do_sign() to sign something on a Mac, and if the key in question corresponds to the NIST P256 elliptic curve type, it goes down the ECDSA_do_sign_new() path and never calls the registered callback. This is the only key type supported by the Apple Secure Enclave, so I assume it's special-cased to do something with that. Unfortunately the consequence is that it's impossible to use a PKCS#11 module that uses Secure Enclave keys with the shipped version of OpenSSH under macOS. For now I'm working around this with an SSH agent built using Go's agent module, forwarding most requests through to the default session agent but appending hardware-backed keys and implementing signing with them, which is probably what I should have done in the first place.

There's a bunch of ways you can store cryptographic keys. The most obvious is to just stick them on disk, but that has the downside that anyone with access to the system could just steal them and do whatever they wanted with them. At the far end of the scale you have Hardware Security Modules (HSMs), hardware devices that are specially designed to self destruct if you try to take them apart and extract the keys, and which will generate an audit trail of every key operation. In between you have things like smartcards, TPMs, Yubikeys, and other platform secure enclaves - devices that don't allow arbitrary access to keys, but which don't offer the same level of assurance as an actual HSM (and are, as a result, orders of magnitude cheaper).

The problem with all of these hardware approaches is that they have entirely different communication mechanisms. The industry realised this wasn't ideal, and in 1994 RSA released version 1 of the PKCS#11 specification. This defines a C interface with a single entry point - C_GetFunctionList. Applications call this and are given a structure containing function pointers, with each entry corresponding to a PKCS#11 function. The application can then simply call the appropriate function pointer to trigger the desired functionality, such as "Tell me how many keys you have" and "Sign this, please". This is both an example of C not just being a programming language and also of you having to shove a bunch of vendor-supplied code into your security critical tooling, but what could possibly go wrong.

(Linux distros work around this problem by using p11-kit, which is a daemon that speaks d-bus and loads PKCS#11 modules for you. You can either speak to it directly over d-bus, or for apps that only speak PKCS#11 you can load a module that just transports the PKCS#11 commands over d-bus. This moves the weird vendor C code out of process, and also means you can deal with these modules without having to speak the C ABI, so everyone wins)

One of my work tasks at the moment is helping secure SSH keys, ensuring that they're only issued to appropriate machines and can't be stolen afterwards. For Windows and Linux machines we can stick them in the TPM, but Macs don't have a TPM as such. Instead, there's the Secure Enclave - part of the T2 security chip on x86 Macs, and directly integrated into the M-series SoCs. It doesn't have anywhere near as many features as a TPM, let alone an HSM, but it can generate NIST curve elliptic curve keys and sign things with them and that's good enough. Things are made more complicated by Apple only allowing keys to be used by the app that generated them, so it's hard for applications to generate keys on behalf of each other. This can be mitigated by using CryptoTokenKit, an interface that allows apps to present tokens to the systemwide keychain. Although this is intended for allowing a generic interface for access to such tokens (kind of like PKCS#11), an app can generate its own keys in the Secure Enclave and then expose them to other apps via the keychain through CryptoTokenKit.

Of course, applications then need to know how to communicate with the keychain. Browsers mostly do so, and Apple's version of SSH can to an extent. Unfortunately, that extent is "Retrieve passwords to unlock on-disk keys", which doesn't help in our case. PKCS#11 comes to the rescue here! Apple ship a module called ssh-keychain.dylib, a PKCS#11 module that's intended to allow SSH to use keys that are present in the system keychain. Unfortunately it's not super well maintained - it got broken when Big Sur moved all the system libraries into a cache, but got fixed up a few releases later. Unfortunately every time I tested it with our CryptoTokenKit provider (and also when I retried with SecureEnclaveToken to make sure it wasn't just our code being broken), ssh would tell me "provider /usr/lib/ssh-keychain.dylib returned no slots" which is not especially helpful. Finally I realised that it was actually generating more debug output, but it was being sent to the system debug logs rather than the ssh debug output. Well, when I say "more debug output", I mean "Certificate []: algorithm is not supported, ignoring it", which still doesn't tell me all that much. So I stuck it in Ghidra and searched for that string, and the line above it was

iVar2 = __auth_stubs::_objc_msgSend(uVar7,"isEqual:",*(undefined8*)__got::_kSecAttrKeyTypeRSA);

with it immediately failing if the key isn't RSA. Which it isn't, since the Secure Enclave doesn't support RSA. Apple's PKCS#11 module appears incapable of making use of keys generated on Apple's hardware.

There's a couple of ways of dealing with this. The first, which is taken by projects like Secretive, is to implement the SSH agent protocol and have SSH delegate key management to that agent, which can then speak to the keychain. But if you want this to work in all cases you need to implement all the functionality in the existing ssh-agent, and that seems like a bunch of work. The second is to implement a PKCS#11 module, which sounds like less work but probably more mental anguish. I'll figure that out tomorrow.

I've written about bearer tokens and how much pain they cause me before, but sadly wishing for a better world doesn't make it happen so I'm making do with what's available. Okta has a feature called Device Trust which allows to you configure access control policies that prevent people obtaining tokens unless they're using a trusted device. This doesn't actually bind the tokens to the hardware in any way, so if a device is compromised or if a user is untrustworthy this doesn't prevent the token ending up on an unmonitored system with no security policies. But it's an incremental improvement, other than the fact that for desktop it's only supported on Windows and MacOS, which really doesn't line up well with my interests.

Obviously there's nothing fundamentally magic about these platforms, so it seemed fairly likely that it would be possible to make this work elsewhere. I spent a while staring at the implementation using Charles Proxy and the Chrome developer tools network tab and had worked out a lot, and then Okta published a paper describing a lot of what I'd just laboriously figured out. But it did also help clear up some points of confusion and clarified some design choices. I'm not going to give a full description of the details (with luck there'll be code shared for that before too long), but here's an outline of how all of this works. Also, to be clear, I'm only going to talk about the desktop support here - mobile is a bunch of related but distinct things that I haven't looked at in detail yet.

Okta's Device Trust (as officially supported) relies on Okta Verify, a local agent. When initially installed, Verify authenticates as the user, obtains a token with a scope that allows it to manage devices, and then registers the user's computer as an additional MFA factor. This involves it generating a JWT that embeds a number of custom claims about the device and its state, including things like the serial number. This JWT is signed with a locally generated (and hardware-backed, using a TPM or Secure Enclave) key, which allows Okta to determine that any future updates from a device claiming the same identity are genuinely from the same device (you could construct an update with a spoofed serial number, but you can't copy the key out of a TPM so you can't sign it appropriately). This is sufficient to get a device registered with Okta, at which point it can be used with Fastpass, Okta's hardware-backed MFA mechanism.

As outlined in the aforementioned deep dive paper, Fastpass is implemented via multiple mechanisms. I'm going to focus on the loopback one, since it's the one that has the strongest security properties. In this mode, Verify listens on one of a list of 10 or so ports on localhost. When you hit the Okta signin widget, choosing Fastpass triggers the widget into hitting each of these ports in turn until it finds one that speaks Fastpass and then submits a challenge to it (along with the URL that's making the request). Verify then constructs a response that includes the challenge and signs it with the hardware-backed key, along with information about whether this was done automatically or whether it included forcing the user to prove their presence. Verify then submits this back to Okta, and if that checks out Okta completes the authentication.

Doing this via loopback from the browser has a bunch of nice properties, primarily around the browser providing information about which site triggered the request. This means the Verify agent can make a decision about whether to submit something there (ie, if a fake login widget requests your creds, the agent will ignore it), and also allows the issued token to be cross-checked against the site that requested it (eg, if g1thub.com requests a token that's valid for github.com, that's a red flag). It's not quite at the same level as a hardware WebAuthn token, but it has many of the anti-phishing properties.

But none of this actually validates the device identity! The entire registration process is up to the client, and clients are in a position to lie. Someone could simply reimplement Verify to lie about, say, a device serial number when registering, and there'd be no proof to the contrary. Thankfully there's another level to this to provide stronger assurances. Okta allows you to provide a CA root[1]. When Okta issues a Fastpass challenge to a device the challenge includes a list of the trusted CAs. If a client has a certificate that chains back to that, it can embed an additional JWT in the auth JWT, this one containing the certificate and signed with the certificate's private key. This binds the CA-issued identity to the Fastpass validation, and causes the device to start appearing as "Managed" in the Okta device management UI. At that point you can configure policy to restrict various apps to managed devices, ensuring that users are only able to get tokens if they're using a device you've previously issued a certificate to.

I've managed to get Linux tooling working with this, though there's still a few drawbacks. The main issue is that the API only allows you to register devices that declare themselves as Windows or MacOS, followed by the login system sniffing browser user agent and only offering Fastpass if you're on one of the officially supported platforms. This can be worked around with an extension that spoofs user agent specifically on the login page, but that's still going to result in devices being logged as a non-Linux OS which makes interpreting the logs more difficult. There's also no ability to choose which bits of device state you log: there's a couple of existing integrations, and otherwise a fixed set of parameters that are reported. It'd be lovely to be able to log arbitrary material and make policy decisions based on that.

This also doesn't help with ChromeOS. There's no real way to automatically launch something that's bound to localhost (you could probably make this work using Crostini but there's no way to launch a Crostini app at login), and access to hardware-backed keys is kind of a complicated topic in ChromeOS for privacy reasons. I haven't tried this yet, but I think using an enterprise force-installed extension and the chrome.enterprise.platformKeys API to obtain a device identity cert and then intercepting requests to the appropriate port range on localhost ought to be enough to do that? But I've literally never written any Javascript so I don't know. Okta supports falling back from the loopback protocol to calling a custom URI scheme, but once you allow that you're also losing a bunch of the phishing protection, so I'd prefer not to take that approach.

Like I said, none of this prevents exfiltration of bearer tokens once they've been issued, and there's still a lot of ecosystem work to do there. But ensuring that tokens can't be issued to unmanaged machines in the first place is still a step forwards, and with luck we'll be able to make use of this on Linux systems without relying on proprietary client-side tooling.

(Time taken to code this implementation: about two days, and under 1000 lines of new code. Time taken to figure out what the fuck to write: rather a lot longer)

[1] There's also support for having Okta issue certificates, but then you're kind of back to the "How do I know this is my device" situation

Update: There's actually a more detailed writeup of this here that I somehow missed. Original entry follows:

Today I had to deal with a system that had an irritating restriction - a firmware configuration option I really wanted to be able to change appeared as a greyed out entry in the configuration menu. Some emails revealed that this was a deliberate choice on the part of the system vendor, so that seemed to be that. Thankfully in this case there was a way around that.

One of the things UEFI introduced was a mechanism to generically describe firmware configuration options, called Visual Forms Representation (or VFR). At the most straightforward level, this lets you define a set of forms containing questions, with each question associated with a value in a variable. Questions can be made dependent upon the answers to other questions, so you can have options that appear or disappear based on how other questions were answered. An example in this language might be something like:
CheckBox Prompt: "Console Redirection", Help: "Console Redirection Enable or Disable.", QuestionFlags: 0x10, QuestionId: 53, VarStoreId: 1, VarStoreOffset: 0x39, Flags: 0x0
In which question 53 asks whether console redirection should be enabled or disabled. Other questions can then rely on the answer to question 53 to influence whether or not they're relevant (eg, if console redirection is disabled, there's no point in asking which port it should be redirected to). As a checkbox, if it's set then the value will be set to 1, and 0 otherwise. But where's that stored? Earlier we have another declaration:
VarStore GUID: EC87D643-EBA4-4BB5-A1E5-3F3E36B20DA9, VarStoreId: 1, Size: 0xF4, Name: "Setup"
A UEFI variable called "Setup" and with GUID EC87D643-EBA4-4BB5-A1E5-3F3E36B20DA9 is declared as VarStoreId 1 (matching the declaration in the question) and is 0xf4 bytes long. The question indicates that the offset for that variable is 0x39. Rewriting Setup-EC87D643-EBA4-4BB5-A1E5-3F3E36B20DA9 with a modified value in offset 0x39 will allow direct manipulation of the config option.

But how do we get this data in the first place? VFR isn't built into the firmware directly - instead it's turned into something called Intermediate Forms Representation, or IFR. UEFI firmware images are typically in a standardised format, and you can use UEFITool to extract individual components from that firmware. If you use UEFITool to search for "Setup" there's a good chance you'll be able to find the component that implements the setup UI. Running IFRExtractor-RS against it will then pull out any IFR data it finds, and decompile that into something resembling the original VFR. And now you have the list of variables and offsets and the configuration associated with them, even if your firmware has chosen to hide those options from you.

Given that a bunch of these config values may be security relevant, this seems a little concerning - what stops an attacker who has access to the OS from simply modifying these variables directly? UEFI avoids this by having two separate stages of boot, one where the full firmware ("Boot Services") is available, and one where only a subset ("Runtime Services") is available. The transition is triggered by the OS calling ExitBootServices, indicating the handoff from the firmware owning the hardware to the OS owning the hardware. This is also considered a security boundary - before ExitBootServices everything running has been subject to any secure boot restrictions, and afterwards applications can do whatever they want. UEFI variables can be flagged as being visible in both Boot and Runtime Services, or can be flagged as Boot Services only. As long as all the security critical variables are Boot Services only, an attacker should never be able to run untrusted code that could alter them.

In my case, the firmware option I wanted to alter had been enclosed in "GrayOutIf True" blocks. But the questions were still defined and the code that acted on those options was still present, so simply modifying the variables while still inside Boot Services gave me what I wanted. Note that this isn't a given! The presence of configuration options in the IFR data doesn't mean that anything will later actually read and make use of that variable - a vendor may have flagged options as unavailable and then removed the code, but never actually removed the config data. And also please do note that the reason stuff was removed may have been that it doesn't actually work, and altering any of these variables risks bricking your hardware in a way that's extremely difficult to recover. And there's also no requirement that vendors use IFR to describe their configuration, so you may not get any help here anyway.

In summary: if you do this you may break your computer. If you don't break your computer, it might not work anyway. I'm not going to help you try to break your computer. And I didn't come up with any of this, I just didn't find it all written down in one place while I was researching it.

First up: what I'm covering here is probably not relevant for most people. That's ok! Different situations have different threat models, and if what I'm talking about here doesn't feel like you have to worry about it, that's great! Your life is easier as a result. But I have worked in situations where we had to care about some of the scenarios I'm going to describe here, and the technologies I'm going to talk about here solve a bunch of these problems.

So. You run a typical VM in the cloud. Who has access to that VM? Well, firstly, anyone who has the ability to log into the host machine with administrative capabilities. With enough effort, perhaps also anyone who has physical access to the host machine. But the hypervisor also has the ability to inspect what's running inside a VM, so anyone with the ability to install a backdoor into the hypervisor could theoretically target you. And who's to say the cloud platform launched the correct image in the first place? The control plane could have introduced a backdoor into your image and run that instead. Or the javascript running in the web UI that you used to configure the instance could have selected a different image without telling you. Anyone with the ability to get a (cleverly obfuscated) backdoor introduced into quite a lot of code could achieve that. Obviously you'd hope that everyone working for a cloud provider is honest, and you'd also hope that their security policies are good and that all code is well reviewed before being committed. But when you have several thousand people working on various components of a cloud platform, there's always the potential for something to slip up.

Let's imagine a large enterprise with a whole bunch of laptops used by developers. If someone has the ability to push a new package to one of those laptops, they're in a good position to obtain credentials belonging to the user of that laptop. That means anyone with that ability effectively has the ability to obtain arbitrary other privileges - they just need to target someone with the privilege they want. You can largely mitigate this by ensuring that the group of people able to do this is as small as possible, and put technical barriers in place to prevent them from pushing new packages unilaterally.

Now imagine this in the cloud scenario. Anyone able to interfere with the control plane (either directly or by getting code accepted that alters its behaviour) is in a position to obtain credentials belonging to anyone running in that cloud. That's probably a much larger set of people than have the ability to push stuff to laptops, but they have much the same level of power. You'll obviously have a whole bunch of processes and policies and oversights to make it difficult for a compromised user to do such a thing, but if you're a high enough profile target it's a plausible scenario.

How can we avoid this? The easiest way is to take the people able to interfere with the control plane out of the loop. The hypervisor knows what it booted, and if there's a mechanism for the VM to pass that information to a user in a trusted way, you'll be able to detect the control plane handing over the wrong image. This can be achieved using trusted boot. The hypervisor-provided firmware performs a "measurement" (basically a cryptographic hash of some data) of what it's booting, storing that information in a virtualised TPM. This TPM can later provide a signed copy of the measurements on demand. A remote system can look at these measurements and determine whether the system is trustworthy - if a modified image had been provided, the measurements would be different. As long as the hypervisor is trustworthy, it doesn't matter whether or not the control plane is - you can detect whether you were given the correct OS image, and you can build your trust on top of that.

(Of course, this depends on you being able to verify the key used to sign those measurements. On real hardware the TPM has a certificate that chains back to the manufacturer and uniquely identifies the TPM. On cloud platforms you typically have to retrieve the public key via the metadata channel, which means you're trusting the control plane to give you information about the hypervisor in order to verify what the control plane gave to the hypervisor. This is suboptimal, even though realistically the number of moving parts in that part of the control plane is much smaller than the number involved in provisioning the instance in the first place, so an attacker managing to compromise both is less realistic. Still, AWS doesn't even give you that, which does make it all rather more complicated)

Ok, so we can (largely) decouple our trust in the VM from having to trust the control plane. But we're still relying on the hypervisor to provide those attestations. What if the hypervisor isn't trustworthy? This sounds somewhat ridiculous (if you can't run a trusted app on top of an untrusted OS, how can you run a trusted OS on top of an untrusted hypervisor?), but AMD actually have a solution for that. SEV ("Secure Encrypted Virtualisation") is a technology where (handwavily) an encryption key is generated when a new VM is created, and the memory belonging to that VM is encrypted with that key. The hypervisor has no access to that encryption key, and any access to memory initiated by the hypervisor will only see the encrypted content. This means that nobody with the ability to tamper with the hypervisor can see what's going on inside the OS (and also means that nobody with physical access can either, so that's another threat dealt with).

But how do we know that the hypervisor set this up, and how do we know that the correct image was booted? SEV has support for a "Launch attestation", a CPU generated signed statement that it booted the current VM with SEV enabled. But it goes further than that! The attestation includes a measurement of what was booted, which means we don't need to trust the hypervisor at all - the CPU itself will tell us what image we were given. Perfect.

Except, well. There's a few problems. AWS just doesn't have any VMs that implement SEV yet (there are bare metal instances that do, but obviously you're building your own infrastructure to make that work). Google only seem to provide the launch measurement via the logging service - and they only include the parsed out data, not the original measurement. So, we still have to trust (a subset of) the control plane. Azure provides it via a separate attestation service, but again it doesn't seem to provide the raw attestation and so you're still trusting the attestation service. For the newest generation of SEV, SEV-SNP, this is less of a big deal because the guest can provide its own attestation. But Google doesn't offer SEV-SNP hardware yet, and the driver you need for this only shipped in Linux 5.19 and Azure's SEV Ubuntu images only offer up to 5.15 at the moment, so making use of that means you're putting your own image together at the moment.

And there's one other kind of major problem. A normal VM image provides a bootloader and a kernel and a filesystem. That bootloader needs to run on something. That "something" is typically hypervisor-provided "firmware" - for instance, OVMF. This probably has some level of cloud vendor patching, and they probably don't ship the source for it. You're just having to trust that the firmware is trustworthy, and we're talking about trying to avoid placing trust in the cloud provider. Azure has a private beta allowing users to upload images that include their own firmware, meaning that all the code you trust (outside the CPU itself) can be provided by the user, and once that's GA it ought to be possible to boot Azure VMs without having to trust any Microsoft-provided code.

Well, mostly. As AMD admit, SEV isn't guaranteed to be resistant to certain microarchitectural attacks. This is still much more restrictive than the status quo where the hypervisor could just read arbitrary content out of the VM whenever it wanted to, but it's still not ideal. Which, to be fair, is where we are with CPUs in general.

(Thanks to Leonard Cohnen who gave me a bunch of excellent pointers on this stuff while I was digging through it yesterday)

(Disclaimer: I'm not a cryptographer, and I do not claim to be an expert in Signal. I've had this read over by a couple of people who are so with luck there's no egregious errors, but any mistakes here are mine)

There are indications that Twitter is working on end-to-end encrypted DMs, likely building on work that was done back in 2018. This made use of libsignal, the reference implementation of the protocol used by the Signal encrypted messaging app. There seems to be a fairly widespread perception that, since libsignal is widely deployed (it's also the basis for WhatsApp's e2e encryption) and open source and has been worked on by a whole bunch of cryptography experts, choosing to use libsignal means that 90% of the work has already been done. And in some ways this is true - the security of the protocol is probably just fine. But there's rather more to producing a secure and usable client than just sprinkling on some libsignal.

(Aside: To be clear, I have no reason to believe that the people who were working on this feature in 2018 were unaware of this. This thread kind of implies that the practical problems are why it didn't ship at the time. Given the reduction in Twitter's engineering headcount, and given the new leadership's espousal of political and social perspectives that don't line up terribly well with the bulk of the cryptography community, I have doubts that any implementation deployed in the near future will get all of these details right)

I was musing about this last night and someone pointed out some prior art. Bridgefy is a messaging app that uses Bluetooth as its transport layer, allowing messaging even in the absence of data services. The initial implementation involved a bunch of custom cryptography, enabling a range of attacks ranging from denial of service to extracting plaintext from encrypted messages. In response to criticism Bridgefy replaced their custom cryptographic protocol with libsignal, but that didn't fix everything. One issue is the potential for MITMing - keys are shared on first communication, but the client provided no mechanism to verify those keys, so a hostile actor could pretend to be a user, receive messages intended for that user, and then reencrypt them with the user's actual key. This isn't a weakness in libsignal, in the same way that the ability to add a custom certificate authority to a browser's trust store isn't a weakness in TLS. In Signal the app key distribution is all handled via Signal's servers, so if you're just using libsignal you need to implement the equivalent yourself.

The other issue was more subtle. libsignal has no awareness at all of the Bluetooth transport layer. Deciding where to send a message is up to the client, and these routing messages were spoofable. Any phone in the mesh could say "Send messages for Bob here", and other phones would do so. This should have been a denial of service at worst, since the messages for Bob would still be encrypted with Bob's key, so the attacker would be able to prevent Bob from receiving the messages but wouldn't be able to decrypt them. However, the code to decide where to send the message and the code to decide which key to encrypt the message with were separate, and the routing decision was made before the encryption key decision. An attacker could send a message saying "Route messages for Bob to me", and then another saying "Actually lol no I'm Mallory". If a message was sent between those two messages, the message intended for Bob would be delivered to Mallory's phone and encrypted with Mallory's key.

Again, this isn't a libsignal issue. libsignal encrypted the message using the key bundle it was told to encrypt it with, but the client code gave it a key bundle corresponding to the wrong user. A race condition in the client logic allowed messages intended for one person to be delivered to and readable by another.

This isn't the only case where client code has used libsignal poorly. The Bond Touch is a Bluetooth-connected bracelet that you wear. Tapping it or drawing gestures sends a signal to your phone, which culminates in a message being sent to someone else's phone which sends a signal to their bracelet, which then vibrates and glows in order to indicate a specific sentiment. The idea is that you can send brief indications of your feelings to someone you care about by simply tapping on your wrist, and they can know what you're thinking without having to interrupt whatever they're doing at the time. It's kind of sweet in a way that I'm not, but it also advertised "Private Spaces", a supposedly secure way to send chat messages and pictures, and that seemed more interesting. I grabbed the app and disassembled it, and found it was using libsignal. So I bought one and played with it, including dumping the traffic from the app. One important thing to realise is that libsignal is just the protocol library - it doesn't implement a server, and so you still need some way to get information between clients. And one of the bits of information you have to get between clients is the public key material.

Back when I played with this earlier this year, key distribution was implemented by uploading the public key to a database. The other end would download the public key, and everything works out fine. And this doesn't sound like a problem, given that the entire point of a public key is to be, well, public. Except that there was no access control on this database, and the filenames were simply phone numbers, so you could overwrite anyone's public key with one of your choosing. This didn't let you cause messages intended for them to be delivered to you, so exploiting this for anything other than a DoS would require another vulnerability somewhere, but there are contrived situations where this would potentially allow the privacy expectations to be broken.

Another issue with this app was its handling of one-time prekeys. When you send someone new a message via Signal, it's encrypted with a key derived from not only the recipient's identity key, but also from what's referred to as a "one-time prekey". Users generate a bunch of keypairs and upload the public half to the server. When you want to send a message to someone, you ask the server for one of their one-time prekeys and use that. Decrypting this message requires using the private half of the one-time prekey, and the recipient deletes it afterwards. This means that an attacker who intercepts a bunch of encrypted messages over the network and then later somehow obtains the long-term keys still won't be able to decrypt the messages, since they depended on keys that no longer exist. Since these one-time prekeys are only supposed to be used once (it's in the name!) there's a risk that they can all be consumed before they're replenished. The spec regarding pre-keys says that servers should consider rate-limiting this, but the protocol also supports falling back to just not using one-time prekeys if they're exhausted (you lose the forward secrecy benefits, but it's still end-to-end encrypted). This implementation not only implemented no rate-limiting, making it easy to exhaust the one-time prekeys, it then also failed to fall back to running without them. Another easy way to force DoS.

(And, remember, a successful DoS on an encrypted communications channel potentially results in the users falling back to an unencrypted communications channel instead. DoS may not break the encrypted protocol, but it may be sufficient to obtain plaintext anyway)

And finally, there's ClearSignal. I looked at this earlier this year - it's avoided many of these pitfalls by literally just being a modified version of the official Signal client and using the existing Signal servers (it's even interoperable with Actual Signal), but it's then got a bunch of other weirdness. The Signal database (I /think/ including the keys, but I haven't completely verified that) gets backed up to an AWS S3 bucket, identified using something derived from a key using KERI, and I've seen no external review of that whatsoever. So, who knows. It also has crash reporting enabled, and it's unclear how much internal state it sends on crashes, and it's also based on an extremely old version of Signal with the "You need to upgrade Signal" functionality disabled.

Three clients all using libsignal in one form or another, and three clients that do things wrong in ways that potentially have a privacy impact. Again, none of these issues are down to issues with libsignal, they're all in the code that surrounds it. And remember that Twitter probably has to worry about other issues as well! If I lose my phone I'm probably not going to worry too much about whether the messages sent through my weird bracelet app being gone forever, but losing all my Twitter DMs would be a significant change in behaviour from the status quo. But that's not an easy thing to do when you're not supposed to have access to any keys! Group chats? That's another significant problem to deal with. And making the messages readable through the web UI as well as on mobile means dealing with another set of key distribution issues. Get any of this wrong in one way and the user experience doesn't line up with expectations, get it wrong in another way and the worst case involves some of your users in countries with poor human rights records being executed.

Simply building something on top of libsignal doesn't mean it's secure. If you want meaningful functionality you need to build a lot of infrastructure around libsignal, and doing that well involves not just competent development and UX design, but also a strong understanding of security and cryptography. Given Twitter's lost most of their engineering and is led by someone who's alienated all the cryptographers I know, I wouldn't be optimistic.

One of the huge benefits of WebAuthn is that it makes traditional phishing attacks impossible. An attacker sends you a link to a site that looks legitimate but isn't, and you type in your credentials. With SMS or TOTP-based 2FA, you type in your second factor as well, and the attacker now has both your credentials and a legitimate (if time-limited) second factor token to log in with. WebAuthn prevents this by verifying that the site it's sending the secret to is the one that issued it in the first place - visit an attacker-controlled site and said attacker may get your username and password, but they won't be able to obtain a valid WebAuthn response.

But what if there was a mechanism for an attacker to direct a user to a legitimate login page, resulting in a happy WebAuthn flow, and obtain valid credentials for that user anyway? This seems like the lead-in to someone saying "The Aristocrats", but unfortunately it's (a) real, (b) RFC-defined, and (c) implemented in a whole bunch of places that handle sensitive credentials. The villain of this piece is RFC 8628, and while it exists for good reasons it can be used in a whole bunch of ways that have unfortunate security consequences.

What is the RFC 8628-defined Device Authorization Grant, and why does it exist? Imagine a device that you don't want to type a password into - either it has no input devices at all (eg, some IoT thing) or it's awkward to type a complicated password (eg, a TV with an on-screen keyboard). You want that device to be able to access resources on behalf of a user, so you want to ensure that that user authenticates the device. RFC 8628 describes an approach where the device requests the credentials, and then presents a code to the user (either on screen or over Bluetooth or something), and starts polling an endpoint for a result. The user visits a URL and types in that code (or is given a URL that has the code pre-populated) and is then guided through a standard auth process. The key distinction is that if the user authenticates correctly, the issued credentials are passed back to the device rather than the user - on successful auth, the endpoint the device is polling will return an oauth token.

But what happens if it's not a device that requests the credentials, but an attacker? What if said attacker obfuscates the URL in some way and tricks a user into clicking it? The user will be presented with their legitimate ID provider login screen, and if they're using a WebAuthn token for second factor it'll work correctly (because it's genuinely talking to the real ID provider!). The user will then typically be prompted to approve the request, but in every example I've seen the language used here is very generic and doesn't describe what's going on or ask the user. AWS simply says "An application or device requested authorization using your AWS sign-in" and has a big "Allow" button, giving the user no indication at all that hitting "Allow" may give a third party their credentials.

This isn't novel! Christoph Tafani-Dereeper has an excellent writeup on this topic from last year, which builds on Nestori Syynimaa's earlier work. But whenever I've talked about this, people seem surprised at the consequences. WebAuthn is supposed to protect against phishing attacks, but this approach subverts that protection by presenting the user with a legitimate login page and then handing their credentials to someone else.

RFC 8628 actually recognises this vector and presents a set of mitigations. Unfortunately nobody actually seems to implement these, and most of the mitigations are based around the idea that this flow will only be used for physical devices. Sadly, AWS uses this for initial authentication for the aws-cli tool, so there's no device in that scenario. Another mitigation is that there's a relatively short window where the code is valid, and so sending a link via email is likely to result in it expiring before the user clicks it. An attacker could avoid this by directing the user to a domain under their control that triggers the flow and then redirects the user to the login page, ensuring that the code is only generated after the user has clicked the link.

Can this be avoided? The best way to do so is to ensure that you don't support this token issuance flow anywhere, or if you do then ensure that any tokens issued that way are extremely narrowly scoped. Unfortunately if you're an AWS user, that's probably not viable - this flow is required for the cli tool to perform SSO login, and users are going to end up with broadly scoped tokens as a result. The logs are also not terribly useful.

The infuriating thing is that this isn't necessary for CLI tooling. The reason this approach is taken is that you need a way to get the token to a local process even if the user is doing authentication in a browser. This can be avoided by having the process listen on localhost, and then have the login flow redirect to localhost (including the token) on successful completion. In this scenario the attacker can't get access to the token without having access to the user's machine, and if they have that they probably have access to the token anyway.

There's no real moral here other than "Security is hard". Sorry.

Fast laptops are expensive, cheap laptops are slow. But even a fast laptop is slower than a decent workstation, and if your developers want a local build environment they're probably going to want a decent workstation. They'll want a fast (and expensive) laptop as well, though, because they're not going to carry their workstation home with them and obviously you expect them to be able to work from home. And in two or three years they'll probably want a new laptop and a new workstation, and that's even more money. Not to mention the risks associated with them doing development work on their laptop and then drunkenly leaving it in a bar or having it stolen or the contents being copied off it while they're passing through immigration at an airport. Surely there's a better way?

This is the thinking that leads to "Let's give developers a Chromebook and a VM running in the cloud". And it's an appealing option! You spend far less on the laptop, and the VM is probably cheaper than the workstation - you can shut it down when it's idle, you can upgrade it to have more CPUs and RAM as necessary, and you get to impose all sorts of additional neat security policies because you have full control over the network. You can run a full desktop environment on the VM, stream it to a cheap laptop, and get the fast workstation experience on something that weighs about a kilogram. Your developers get the benefit of a fast machine wherever they are, and everyone's happy.

But having worked at more than one company that's tried this approach, my experience is that very few people end up happy. I'm going to give a few reasons here, but I can't guarantee that they cover everything - and, to be clear, many (possibly most) of the reasons I'm going to describe aren't impossible to fix, they're simply not priorities. I'm also going to restrict this discussion to the case of "We run a full graphical environment on the VM, and stream that to the laptop" - an approach that only offers SSH access is much more manageable, but also significantly more restricted in certain ways. With those details mentioned, let's begin.

The first thing to note is that the overall experience is heavily tied to the protocol you use for the remote display. Chrome Remote Desktop is extremely appealing from a simplicity perspective, but is also lacking some extremely key features (eg, letting you use multiple displays on the local system), so from a developer perspective it's suboptimal. If you read the rest of this post and want to try this anyway, spend some time working with your users to find out what their requirements are and figure out which technology best suits them.

Second, let's talk about GPUs. Trying to run a modern desktop environment without any GPU acceleration is going to be a miserable experience. Sure, throwing enough CPU at the problem will get you past the worst of this, but you're still going to end up with users who need to do 3D visualisation, or who are doing VR development, or who expect WebGL to work without burning up every single one of the CPU cores you so graciously allocated to their VM. Cloud providers will happily give you GPU instances, but that's going to cost more and you're going to need to re-run your numbers to verify that this is still a financial win. "But most of my users don't need that!" you might say, and we'll get to that later on.

Next! Video quality! This seems like a trivial point, but if you're giving your users a VM as their primary interface, then they're going to do things like try to use Youtube inside it because there's a conference presentation that's relevant to their interests. The obvious solution here is "Do your video streaming in a browser on the local system, not on the VM" but from personal experience that's a super awkward pain point! If I click on a link inside the VM it's going to open a browser there, and now I have a browser in the VM and a local browser and which of them contains the tab I'm looking for WHO CAN SAY. So your users are going to watch stuff inside their VM, and re-compressing decompressed video is going to look like shit unless you're throwing a huge amount of bandwidth at the problem. And this is ignoring the additional irritation of your browser being unreadable while you're rapidly scrolling through pages, or terminal output from build processes being a muddy blur of artifacts, or the corner case of "I work for Youtube and I need to be able to examine 4K streams to determine whether changes have resulted in a degraded experience" which is a very real job and one that becomes impossible when you pass their lovingly crafted optimisations through whatever codec your remote desktop protocol has decided to pick based on some random guesses about the local network, and look everyone is going to have a bad time.

The browser experience. As mentioned before, you'll have local browsers and remote browsers. Do they have the same security policy? Who knows! Are all the third party services you depend on going to be ok with the same user being logged in from two different IPs simultaneously because they lost track of which browser they had an open session in? Who knows! Are your users going to become frustrated? Who knows oh wait no I know the answer to this one, it's "yes".

Accessibility! More of your users than you expect rely on various accessibility interfaces, be those mechanisms for increasing contrast, screen magnifiers, text-to-speech, speech-to-text, alternative input mechanisms and so on. And you probably don't know this, but most of these mechanisms involve having accessibility software be able to introspect the UI of applications in order to provide appropriate input or expose available options and the like. So, I'm running a local text-to-speech agent. How does it know what's happening in the remote VM? It doesn't because it's just getting an a/v stream, so you need to run another accessibility stack inside the remote VM and the two of them are unaware of each others existence and this works just as badly as you'd think. Alternative input mechanism? Good fucking luck with that, you're at best going to fall back to "Send synthesized keyboard inputs" and that is nowhere near as good as "Set the contents of this text box to this unicode string" and yeah I used to work on accessibility software maybe you can tell. And how is the VM going to send data to a braille output device? Anyway, good luck with the lawsuits over arbitrarily making life harder for a bunch of members of a protected class.

One of the benefits here is supposed to be a security improvement, so let's talk about WebAuthn. I'm a big fan of WebAuthn, given that it's a multi-factor authentication mechanism that actually does a good job of protecting against phishing, but if my users are running stuff inside a VM, how do I use it? If you work at Google there's a solution, but that does mean limiting yourself to Chrome Remote Desktop (there are extremely good reasons why this isn't generally available). Microsoft have apparently just specced a mechanism for doing this over RDP, but otherwise you're left doing stuff like forwarding USB over IP, and that means that your USB WebAuthn no longer works locally. It also doesn't work for any other type of WebAuthn token, such as a bluetooth device, or an Apple TouchID sensor, or any of the Windows Hello support. If you're planning on moving to WebAuthn and also planning on moving to remote VM desktops, you're going to have a bad time.

That's the stuff that comes to mind immediately. And sure, maybe each of these issues is irrelevant to most of your users. But the actual question you need to ask is what percentage of your users will hit one or more of these, because if that's more than an insignificant percentage you'll still be staffing all the teams that dealt with hardware, handling local OS installs, worrying about lost or stolen devices, and the glorious future of just being able to stop worrying about this is going to be gone and the financial benefits you promised would appear are probably not going to work out in the same way.

A lot of this falls back to the usual story of corporate IT - understand the needs of your users and whether what you're proposing actually meets them. Almost everything I've described here is a corner case, but if your company is larger than about 20 people there's a high probability that at least one person is going to fall into at least one of these corner cases. You're going to need to spend a lot of time understanding your user population to have a real understanding of what the actual costs are here, and I haven't seen anyone do that work before trying to launch this and (inevitably) going back to just giving people actual computers.

There are alternatives! Modern IDEs tend to support SSHing out to remote hosts to perform builds there, so as long as you're ok with source code being visible on laptops you can at least shift the "I need a workstation with a bunch of CPU" problem out to the cloud. The laptops are going to need to be more expensive because they're also going to need to run more software locally, but it wouldn't surprise me if this ends up being cheaper than the full-on cloud desktop experience in most cases.

Overall, the most important thing to take into account here is that your users almost certainly have more use cases than you expect, and this sort of change is going to have direct impact on the workflow of every single one of your users. Make sure you know how much that's going to be, and take that into consideration when suggesting it'll save you money.