The SOC2 Starting Seven | Hacker News Reader

The SOC2 Starting Seven

latacora.singles

109 pointslvh65 comments

Very good post. This ticks all the boxes on the fundamentals when spinning up a security program.

SOC2 Type2 is really where you want to be, but it takes time. Navigating compliance for startups is pretty challenging and I see so many not having a clue how to navigate sales without certs but it's super doable, and getting these things finished get you pretty far along towards Soc2 type1, and shows a lot of goodwill to share these practices even _before_ you have any certs

I'd like more detail on the advantages of AWS AssumeRole, and what attacks it is designed to protect against. It must be more than CloudTrail logs, because normal API usage gets logged to CloudTrail.

One thing I'd like to highlight is that SOC2 is about having controls (of your choosing), and documenting and proving you are following those controls. I think it is important to pick controls you actually want to follow, and that those controls aren't so specific that you get fenced in to a bad process.

I've worked at a few companies that have gone through SOC2, one of them (Dropbox) did it very well. I think the average engineer didn't need to know about SOC2, or what all the controls were, because the controls were well thought out, and automation took care of the proof. At another company every engineer was constantly saying "you have to do that because of SOC2", because the controls intruded on the way engineers worked.

"SOC2 requires that two people approve every PR". Hmm, no the accountants that created SOC2 don't know what PRs are. "Only members of the team called 'QA' are allowed to transition Jira tickets from state A to state B, SOC2 requires it". No, I'm pretty user SOC2 doesn't specify issue tracker workflows. "You need to name your git branched XYZ-abc-foo-bar, because of SOC2". You're telling me that accountants are specifying source control conventions?

The way it works best is when you have multiple accounts ,you have a single Identity account, which is where your user accounts live. This account basically allows sign in and assume role - oh and you can't assume unless you have authenticated with MFA.

Then, all your other accounts - dev, prod, service, whatever - simply have roles and no user management overhead - i.e you aren't duplicating users in a bunch of accounts and having to deal with a bunch of different identities.

SSO is based on AssumeRole which issues temporary credentials (session tokens) instead of using static credentials. SSO-like centralized access management is important to prove that when someone leaves your company that you cut off their access to all data and systems, much easier to do that when everyone uses SSO.

SOC2 doesn’t specify git branch logistics. In general you need to prove all system changes were reviewed, justified, and approved by another person. The goal is no single person can deploy unsupervised production system changes, and the justification for changes were approved and documented. How you do that is all in the art of IT.

As mentioned, AssumeRole is a critical part of a multi-account strategy, which is considered an AWS best practice. In addition to that, it is an integral part of an SSO strategy. Ideally, instead of a pile of IAM users with separate credentials, user identities should be federated from your identity provider (like Auth0, Ping, AzureAD, whatever). There are a number of setups, but they all boil down to your users trading their corporate identity for temporary AWS credentials via something like an AssumeRoleWithSAML call. This is only slightly more complicated to set up than a good IAM user/group architecture, but has the benefit of not needing to deal with IAM users and multiple sets of identities for your users. You can also map particular roles back to something like AD groups to control who can assume what.

Thanks, that was a very clear explanation. I know AssumeRole is needed for SSO, and I understand the benefits of SSO. The way the article phrased it it sounded like AssumeRole has some very specific benefit by itself.

And if the answer is "short lived credential", then I'd like to understand how short lived credentials that require a long lived credentials to get them are better than long lived credentials, if both can be just as easily revoked.

Honestly, this misses a huge point and does more harm than good. Having some of these things in place is fine of course, but it don't really help you much, nor is most of it required.

SOC2 does not require: SSO, MDM, or almost anything specifically (And what's with the JAMF pro recommendation? MDM is more than iPhones). What it does require are controls. It does not specify what those controls are. You need to create them yourself, and they need to be sufficient to meet the requirements of the Trust Services Criteria. And to have controls, you need to know what you are controlling and why.

This brings me to my point: To succeed in SOC2 you actually have to have a plan. You have to have written, reviewed, implemented, and audited policies. THAT is the single biggest hurdle for most companies.

You also need to know how to do a risk assessment on your organization. This is not terribly hard, but it is essential to SOC2.

And finally, you need buy-in from the governing bodies of your organization.

None of these things I mentioned are products. You can't buy them. They take work. A hell of a lot of work. I will guarantee that most companies doing this for the first time do not have half of the processes in place that SOC2 requires. I doubt that 20% have internal audit procedures, for example, or sufficient end-user training.

And one more thing that will take nearly anyone who had done security by surprise if they don't know it's there. The COSO Principles. These were added to SOC2 in the wake of the Lehman Bros/Enron scandal. They extend SOC2 to the entire governance structure of your organization, and include controls on financial reporting, hiring practices, employee review processes, etc. This is a major PITA, because it lies far outside the bailiwick of most CISOs or equivalent, and, again, it requires extensive cooperation from the rest of senior management.

As you can probably tell, I've done this before.

We've watched our clients get SOC2 certified and been directly involved in the IRL and audit interview processes, and circulated this among peers that have also been SOC2 certified, and we're pretty comfortable with the advice we're offering. So:

As we've said repeatedly, SOC2 doesn't "require" much of anything. It certainly doesn't call SSO or MDM out by name. What it instead involves are abstract control points that are addressed with evidence. As the top of the post says, the point is to engage in security engineering practices that generate evidence useful in SOC2 engagements.

So, you can certainly freestyle your application and infra access controls, and make up policy responses to the IRL questions on the fly. You can also sit around and worry about which of the "COSO Principles" you're covered on or not covered on.

Or, you can do some basic sensible security engineering things that are almost certain to cover the majority of the evidence requests your auditors generate, in most cases without even needing to be aware of the AICPA guidance line items.

You make your own process recommendation here: do a "hell of a lot of work" to have "written and audited policies" and a "risk assessment" and become aware of the "COSO Principles". I have no trouble believing that approach works, because after seeing and being involved in a bunch of SOC2 audits and talking to people who did SOC2 audits, I believe everything works.

More importantly, we see startups led around by the nose by insane questionnaires (and a SOC2 IRL is certainly that). We've talked to firms that have been told by their SOC2 auditors to install IDS systems, WAFs, and Mac AV software. We are alarmed by the prospect of a startup without in-house security or compliance expertise reading what's out there about SOC2 --- especially the AICPA documentation, or example IRLs --- and then just going and doing that stuff. They'd be wasting a tremendous amount of time without realizing that smart startups skip a lot of that work and deploy none of the junk and get SOC2'd just fine.

So, if you're going to do something, do something sensible.

What I think people should be especially careful about is taking advice from people who have just done SOC2 at a single company or with a single auditor. They are all different. There are processes where you'll end up explaining what a URL is. There are processes where you'll end up explaining why you have VPC flow logs disabled. The value we're offering here is that we've seen it done repeatedly, with multiple auditors.

Look, I agree with pretty much all of what you say. I would never suggest any company, whether a startup or an established enterprise (which is my case) go through the SOC2 process unguided, attempting to interpret the ACIPA docs on their own. That is a recipe for disaster. The TSC is almost inscrutable on its own. The AICPA cannot write in plain english to save their life.

That said, I don't understand this statement: "You can also sit around and worry about which of the "COSO Principles" you're covered on or not covered on."

In the end, to pass a SOC2 audit, you have to have evidence for each of the applicable TSC points, including the COSO Principles, which have little or nothing to do with information security but are all about general business governance. It's not a question of "sitting around wondering." It's understanding what the COSO Principles actually are after, so that you can assemble the appropriate evidence. And that means working with HR and finance.

You make it sound like the COSO Principles are irrelevant. Believe me, if I could skip them I would. If I could skip a risk assessment, I would. If I could skip all the "written and audited policies" I would. But you can't skip them. And in the case of a risk assessment, you shouldn't skip them. I mean, that's the whole point in the end: knowing your risks, and having the controls in place to mitigate them.

So yes, of course you need to be sensible. But you also have to do the work, and the work is hard. It is by far the last favorite part of my job.

But my point is: It's not about the product category boxes you have ticked. Security products are important. They make compliance much easer. No question. But for SOC2 to have real value to an organization (and I think there is real value that can be gained from it), it is far more about process, and it is process that is the most difficult thing to implement and religiously maintain and document.

This has simply not been my experience of how SOC2 processes have actually worked at real startups. The experience I've seen, repeatedly, in variations but always on this one theme, is of a collection of mostly boilerplate policies being exchanged for a turbocharged vendorsec questionnaire, followed by a series of interviews. The line items on the questionnaire are answered in any ways that is convenient for the auditee and credible for the auditor.

At no point is anyone on the engineering side made familiar with TSC points or COSO; the runic accountancy is driven be the auditor. I would, in particular, not recommend that startups thinking about pursuing SOC2 spend a lot of time familiarizing themselves with the TSC or (god forbid) the COSO Framework, because it simply isn't going to matter.

My general belief is that SOC2 is of no intrinsic value to organizations, and going into it with a mind towards letting your engineering practice be guided by SOC2 rather than dictating SOC2 is a recipe for heartbreak. Among security engineers (and managers) at tech startups I've talked to, I don't seem to be far out of the mainstream. SOC2 is like most university degrees: it's a demonstration of seriousness, and nothing more.

If you think this blog post is about "buying the right products", you've entirely missed its point.

> And what's with the JAMF pro recommendation? MDM is more than iPhones

JAMF Pro is not just for iPhones.

I know what Jamf Pro is. We manage all our Mac an iOS devices with it. But it's not for Android, or Chrome, or Windows. This article makes the assumption that all startups use Mac. That's a rather dubious assumption.

Saying it was just for phones is your quote, so I think your reaction is a little misplaced. If you don’t want people to tell you what Jamf Pro does then maybe don’t make being wrong about your what Jamf Pro does part of your argument.

(Plus, if you think this is about buying any particular product, you have woefully missed the point.)

Maybe don't read one parenthetical statement, assume it has any bearing on my argument, ignore the rest of what I wrote, and treat me like I don't know anything. That's just rude. I bought the damn thing specifically to manage a fleet of ~350 Macs. I know what it is.

No it isn't. Have you met a startup?

>Any time anything security relevant incident happens, you could make a private Slack channel named for the incident.

This might be a good start, but it makes me a little uncomfortable. In a true incident, there is a metric ton of stuff that I would not want to be discoverable. I like to set aside an area with locked-down access to keep the truly toxic material found during a serious incident.

And for startups or other small companies reading this--the things mentioned here should not be a big deal or take enormous time to do. The earlier you do what is recommended in the post, the happier everyone will be.

I'm reminded of my Dad's saying: Tires are like insurance: When you need it, it is too late.

[edit typo]

A couple people told me the same thing, and I think it's a valid concern as security process. On the other hand: Slack-channel IR has worked well for clients of ours as a compliance step, and having Slack-channel IR is better than having no IR from a security posture perspective.

That's a good point. Even just using Github or Gitlab issues to track incidents with approvals is better than nothing.

Any suggestions for MDM for Linux laptops? Most device management solutions I have seen are for either Windows or Mac, but is there one that is accepted by auditors and is not utter garbage UX wise for the user on Linux, where the user is most likely going to want and have full admin access to their own laptop? (I.e. since the user in question is a developer, I feel a strong aversion to not trusting them to do system administration on their own laptop.)

We passed our SOC2 Type 2 audit without any MDM - we're just doing a manual quarterly audit on machines to check that they're update to date.

MDM helps to detect issues earlier, and can remove the need for manual audits, but is not a hard requirement - same with most other things in SOC2.

We've been looking into Osquery. It's open source and appears to be very lightweight. Has anyone else used it?

https://www.osquery.io/

osquery is great and, while it does not tick precisely the same checkboxes as Jamf or Fleetsmith, it'll almost certainly suffice for evidence generation for compliance (osquery is in fact much better at producing "evidence" than most MDM tools are).

Just a shameless plug we've written thousands of queries to automate many compliance checks against major frameworks such as: NCSC-CE, CIS, SOC and ISO. https://www.zercurity.com/product/compliance/ It'll even collate all the evidence for you and help your employees improve their own cyber security posture based on your corporate policies.

> Another bonus point: standardize everyone on Chrome.

The next sentence was worse:

> We don’t have to grumble about why; we’ll just observe that this is what almost every security team does anyways.

I've been through the process before and just went through it again, and the first thing listed (Single Sign-On) is not required at all. I'm not even sure it's mentioned directly in the AICPA criteria.

I'm also not sure what SSO really buys you, except for just moving the criteria target to another SOC-2 report. ;)

Also, MDM is not really critical at all, as long as you have a solid/documented way of managing accounts on web and mobile apps.

I do like the rest of the article except for the list itself, however. SOC-2 is all about documentation and processes. Justifying your security choices is less important than carefully and fully documenting them, and the processes that you have in place.

SOC2 doesn't really "require" much of anything. The question we're answering is: "which security engineering projects can you undertake that will make a SOC2 audit go more smoothly". Because SSO directly addresses a lot of access control control points, and generates a lot of evidence for those control points, and because it's generally a very good practice to have anyways, it'd be the first bit of security engineering we'd recommend to ratchet up your maturity.

What I can tell you is that the IRLs I've seen, both from big 4 auditors and from SOC2 boutiques, have dozens of questions that are directly answered by a sane SSO configuration.

We've watched clients clear SOC2 audits without any coherent SSO. It's clearly doable.

This is all made more tricky by the fact that different SOC2 auditors have different requirements. They're in one sense or another all negotiable, in that you can always switch auditors if they're unreasonable, and we've definitely collected several horror stories about aborted SOC2 processes that were resumed with a different vendor. And, to layer more complexity on that, different bigCo customers will have opinions about who did your SOC2. It's all a mess.

Right, agreed 100%. In terms of security, the value of centralizing credentials is debatable.

The other bit of subtext in this post is that you often have multiple ways of addressing control points auditors bring up, and we'd like to steer startups towards the good ways of doing that. So if an SSO keeps you from having an insane password rotation policy, or an MDM (also not "required") keeps you from installing Mac AV software, it's super worth it to us.

That makes sense to me -- thanks for clarifying!

I feel like that's recognized in the article: we even point out that anti-malware is one of the few (technical) things the AICPA criteria do care about. The point is not that you need SSO, the point is that it is _much simpler_ to demonstrate you've got anything resembling an access control story if you do SSO. You are not doing it because it's the only way, you're doing it because it's the best way.

Agreed! I've run into the malware scanning audit issues at several clients in the past but things have gotten a bit better (or auditors have gotten smarter, since we certainly don't want to install commercial anti-virus software or even ClamAV on certain types of systems): recently, for Linux systems, we successfully used cron-job rootkit scanners/FIM (such as Tiger) to clear the malware scanning hurdles, while on Mac and Windows workstations, client security manuals require built-in anti-virus software (Mac XProtect, Windows Defender).

Maybe! Generally, I get the impression auditors haven't changed their tune much, and we've seen success with people ELI5ing controls and why they are good.

For malware in particular, on the server side, we've seen:

a) auditors not asking after seeing convincing endpoint answers

b) people be successful with scanning container images and then just arguing that containers aren't long-lived enough to matter (and having other infrastructure level controls to argue that if something does leave a container you'll see it somewhere).

That only works if you actually have short-lived containers though, of course :D

> You’re going to sign up for Okta or Google Cloud Identity, tie as many of your applications (first- and third-party) into it, and force 2FA.

Are these really the only options? I'm not terribly comfortable with an external entity owning my SSO--ESPECIALLY Google.

They do mention (but apparently do not recommend) that you can roll your own SSO.

This is really about having SSO, not about Octa or Google.

A lot of really good stuff in here. I have a few questions & quibbles though.

> You’re probably all Macbooks.

What if we're not? Are there any good MDM solutions for Linux? I would prefer not to force macOS on folks who don't want it.

> Another bonus point: standardize everyone on Chrome.

Why not stick with Firefox? It has the advantage of at least trying to keep user information secure.

There's a lot exciting in here, though. I would love to transition to SSH certificates issues by some fancy OAuth2 service. I imagine one could use a named pipe to request them on-demand, so one could just issue 'ssh foo' and everything would Just Work.

The article and the comments here contain a lot of TLAs and the like that many will not be familiar with. Anyone want to expand some of these to save people a bunch of Googling/DDGing/Binging?

  AD AES AICPA CISO
  COSO CSO DEP FDE
  FIM IDS IR JAMF
  LDAP MDM OIDC SOC2
  SSO S/N WAF

I don't recall ever seeing a comment thread with that many such things.

Sorry for any mistakes, mobile.

AD active directory

AES advanced encryption standard

AICPA American Institute of Certified Public Accountants

CISO chief information security officer

COSO risk management framework

CSO many things, probably chief security officer in this context

DEP data execution prevention

FDE full disk encryption

FIM file integrity monitoring

IDS intrusion detection system

IR incident response

JAMF apple device management

LDAP lightweight directory access protocol

MDM mobile device management

OIDC open id connect

SOC2 audit standard

SSO single sign on

S/N serial number

WAF web application firewall

Different DEP here. :) We're talking about the Apple Device Enrollment API.

Thanks, I hadn't yet made it through the full thread for context.

Typo: In the list of "things you don't do" it lists Web Application Firewalls and I thought there's an amusing asterisk for the claim that they "don't work at all"†

But sadly there isn't - that asterisk is supposed to be the next bullet point for Endpoint Protection and AV.

† So many missed opportunities. These things are so awful.

Thanks! Just fixed that.

Also 'log munging' and scene from Love Actually instead of Say Anything

Wait, I can't find Love Actually and Say Anything in the post. Are you talking about a draft?

taped to the boom box playing Peter Gabriel you hold aloft outside their offices

That's Say Anything. It's a movie from the previous century. The scene from Love Actually you can actually recognize from gifs and recent SNL parodies.

It's amazing how many of these recommendations are cloud based. If you have a cloud based box with bad security, anyone can get to it.

If you have a box you own on your own premises, you can have crummy security on that box and still be in good shape.

I like belt and suspenders. 2FA and physical security.

> Sign up for or set up a centralized logging service. It doesn’t matter which. Pipe all your logs to it.

Is there one recommended by HN for multi-platform use?

I'm in the process of preparing for ISO27001 certification and as the topic has arisen, I'd love to get a few opinions if possible.

There are a lot of amazing fancy services available... for a fee. We log billions of lines a year and use GrayLog because the other services are cost prohibitive.

Which is totally fine. Auditors aren't going to care what your log service is. They might, on the other hand, ask you to show evidence of, like, a log line when someone accesses the admin console. You want that to be easy to generate and, just as importantly, you want the process of obtaining that log line to be easy to describe: "go to this one place, type in this one query, save the result". In a perfect world, you want the answers to lots of auditor questions to be the same, perhaps modulo the "one query" you type in to generate the result.

This isn't because the auditor is going to care whether you have to log into 15 different hosts to grep for 20 different log lines; they have no idea what "grep" even is. It's because it's a lot of work to document 15 different processes coherently.

This idea is the basic lens through which people should be reading our recommendations here.

To be clear, when you talk about using SSO with all your applications, are you talking about A) all of the applications your team uses e.g. SaaS like GDocs or AirTable or whatever or B) the application you are creating? e.g. in lieu of your own database?

Or maybe you mean for both?

Both. As much as possible. You'd like as many of the answers to questions about "how do you manage access to this application, know who has access to it, and ensure that people who shouldn't have access to it don't" be "screenshots and logs from your SSO system".

I'd be interested in any opinions as to whether keycloak is an acceptable solution for SSO wrt SOC2. (Hopefully so as we are well committed to it).

SOC2 doesn’t judge which SSO you use (or even if you use SSO).

If you write up your processes with your SSO provider and you follow your processes any SSO (or none!) works.

I guess this is appropriately sceptical about audit at least.

I think people both over and under-estimate audit (in different ways), but certainly if I have to pick it's the over-estimation of the value of audit which hurts and so the scepticism in this piece is warranted.

Maybe! I get the impression there are definitely plenty of people have bought SOC2s the way they also buy pentests: "I'm spending $X0,000 today so I can close $X00,000 in sales tomorrow". Which of course, we as security people would say is spending a lot of money and getting nothing, and the business person says is a necessary expense and something to keep in mind when re-evaluating margins :) (But yes lots of companies also mistake SOC2 for a security audit of course!)

This is a fantastic article overall. As someone who has now gone through SOC 2 twice (first at Dropbox as an IC, now at Fleetsmith as cofounder/CSO, the only part I disagree with is the advice re: MDM.

If you want to make SOC 2 easy, you should choose us (fleetsmith.com) over the competition.

There are some specific things SOC 2 cares about with regard to laptops. The ones that can take effort are:

- User to device inventory attribution ("give me a list of all your Macs and which employees they belong to")

- FileVault enforcement, with automatic (and secure) escrow of the recovery keys

- Enforcement of some kind of AntiVirus (either the native stuff built in to macOS, or deployment of a third party solution like MalwareBytes)

Each of those 3 items are very time-intensive efforts with competing products. With Fleetsmith, each of them are quite literally (not marketing hype) a few clicks.

We're also the leader in terms of security. If you're interested in the intersection of MDM and security research, check out the following:

"Hacking a Brand New Mac Remotely, Right Out of the Box" — Article summarizing research presented at Black Hat 2018.

https://www.wired.com/story/mac-remote-hack-wifi-enterprise/

A Deep Dive into macOS MDM (and how it can be compromised) — 61 page whitepaper related to Black Hat research.

https://i.blackhat.com/us-18/Thu-August-9/us-18-Endahl-A-Dee...

On DEP, MDM, device identity, and authentication — Blog post on the security of the device enrollment process. Includes Fleetsmith’s secure device enrollment implementation, in hopes that other vendors in the space will adopt it.

https://medium.com/fleetsmith/on-dep-mdm-device-identity-and...

An Enterprise Security Roadmap for macOS — Detailed blog post on improvements that Apple should make to macOS and MDM, and why. Includes a detailed list of over 50+ bug reports/feature requests.

https://blog.fleetsmith.com/macos-enterprise-security-roadma...

If anyone is interested in chatting about any of this stuff (the product or the security side) I'm on Twitter at @jesseendahl and on the MacAdmins Slack (macadmins.org) at @jesse.

I have no problem with Fleetsmith and sure Jamf ain't perfect but... just to restate your point briefly: you're claiming "show inventory, turn on FDE, don't fuck up XProtect" are "very time-intensive efforts" with Jamf Pro?

Showing a list of devices is very different than accurate user <-> device attribution. Doing that in competing solutions to Fleetsmith requires at least: (1) having an LDAP server (2) configuring server details, including TLS etc. (3) LDAP attribute mapping in the MDM solution, and then (4) manually assigning each device to a user one a time -- a process that usually involves repeating the following procedure for each device:

1. Copy S/N to clipboard

2. Tab over to inventory spreadsheet

3. Command-F and pray your IT helpdesk recorded which employee the device belongs to

4. Tab back over to the MDM solution, select the employee from the dropdown menu.

This becomes extremely time intensive if you have hundreds or thousands of devices.

As for FDE--enforcing it is easy. Doing that while also reliability and securely escrowing its recovery key is a much different story.

On the reliability side--not every solution out there is equally reliable when it comes to ensuring that the recovery keys actually make it into the MDM.

On the security side, I believe we're the only vendor that does CA pinning across the entire management lifecycle. Those stages are covered in great detail in the previously linked BlackHat whitepaper.

On the server side, I believe we're the only vendor to automatically encrypt sensitive fields (such as FileVault keys) before the hit the database, with per-customer AES keys (key generation and key management handled by Hashicorp Vault's transit backend).

Last but not least, there's the matter of generating evidence for auditors to prove you're doing the things you claim to do. We automatically surface the status of these things in the product, instead of requiring people to input boolean logic and generate custom reports.

Overall, Fleetsmith is just much more "turnkey" when it comes to checking the boxes for SOC 2 than competing MDM solutions.

I'm guessing we have a different opinion on what "competing solutions" or "accurate user <-> device attribution" or "setting up an LDAP server" mean. I'm sure there's a version of this story where somebody picks Intune (it manages everything!) and then decides to run their own AD install (inexplicably) where that description is accurate, but we've seen a pile of people deploy Jamf Pro/Connect to GSuite/Okta and what you're describing does not match my experience.

With GSuite in particular, nobody set up any LDAP. It's an OIDC app, you do not run Connect Verify or Connect Sync. There's LDAP going on when you're authing against Azure, but if you're in that situation AD seems like what you want?

I read your description as suggesting that if you pick anything other than your product, there's necessarily an AD DS or slapd in your future, and I hope we can agree that's definitely not the case. In the most common case for our audience (startups) it's not even any LDAP at all.

Is it fewer clicks in Fleetsmith? Maybe? Probably? And you have to know whatever the hell a "PreStage Enrollment" is which is not as easy as it could be. But I think you're making it sound a lot more hairy than it is, particularly for a deployment with "hundreds or thousands of devices". The hard problem facing that IT team is not finding someone who is unafraid of the words "Preference Domain", come on.

(To reiterate my position: I am not saying Fleetsmith is bad, I'm saying that I think your post makes it sound like anything besides Fleetsmith is a world of pain, and I accept that you probably extra-believe that as someone who founded Fleetsmith (not in the sense of "you're lying" but in the sense of you don't bet the farm on trying to fix things you don't think are broken), but, I think a) whatever Fleetsmith is fine and yes it's probably better at doing the limited set of things you should be doing but b) compared to our experience this is a pretty wide exaggeration of how bad anything else is like.)

My issue with most of these solutions- including this one- is that I don't want separate MDM platforms for my Windows and OSX users.

That's totally fair and you're not alone there. Many people want a "single pane of glass" — one solution that supports both Windows and macOS equally well, but unfortunately it doesn't exist. You're better off going with separate "best of breed" solutions for each platform, or you're bound to be disappointed imo.

I guess that depends a bit on whether your "single pane of glass" is a SOC2 type 2 sales tool, or a real part of your security stance. (I don't _like_ that the first of those options is valuable in some cases, but I do acknowledge it...)

>>> Web Application Firewalls: Most SOC2’d firms don’t use them, and most WAFs don’t work at all.

Most startups are on Cloudflare and Cloudflare does WAF out of the box.

> SOC2 is about documentation, not reality

Yup. If you’re a fixer, knowing this beforehand is going to save you a lot of pain.

What VPN tools support SSO? What's a recommended soution?

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