Context-aware access

In the third session Teresa brings a story from a retailer she used to work for. A buyer's password was stolen through a fake invoice, and the attacker signed in from a hotel computer on another continent and downloaded the supplier price list. 2-step verification would have stopped that particular attack, but Teresa wants a second question asked at every sign-in: not only who is this, but where are they and what are they using? That question is what context-aware access answers. This lesson covers access levels, how they are assigned to apps, the order in which to roll them out, and the mistakes that lock people out.

What context-aware access does

Context-aware access (CAA) lets administrators allow or block access to Workspace apps based on the context of each request: the IP address it comes from, the country, and the state of the device, such as whether it is company-owned, encrypted or running a supported operating system. The decision is made each time the app is used, not only at sign-in, so a laptop that falls out of policy loses access while it is out of policy. Google's help pages list the editions that include it; Birchline's Enterprise Standard and Frontline Standard licenses both do.

The building blocks are access levels. An access level is a named set of conditions, such as Company network (the head office and warehouse IP ranges) or Managed device (a device that Birchline owns or manages, encrypted, with a current operating system). Administrators then assign one or more access levels to an app for an OU or group. A user in that OU can use the app only from a context that meets at least one of the assigned levels.

Device signals and Endpoint Verification

Network conditions are easy to check because every request carries an IP address. Device conditions need information about the device itself. That information comes from endpoint management (lesson 9) for phones and tablets, and, for desktop and laptop computers, from Endpoint Verification, a Chrome extension and helper app that reports the device's operating system, encryption, screen lock and whether it is company-owned. Without that information, Google cannot tell whether a computer is managed, and a level that requires a managed device will treat it as unmanaged.

This is the most common source of trouble in a CAA rollout. Owen will deploy Endpoint Verification to every company laptop through Birchline's device management before any level that depends on device signals is enforced. He also notes that Google's help pages warn that some device details, such as encryption status, can take time to sync after a device is enrolled; a laptop enrolled on a Friday may not meet a level until later.

Assigning levels to apps

Levels do nothing until they are assigned. In the Admin console, under Security, Access and data control, Context-Aware Access, administrators choose an OU or group, choose apps and pick the levels. Several rules govern the result.

• Any level is enough. If an app has two levels assigned, a request that meets either one is allowed.
• Assignments are per OU or group. Different OUs can have different levels for the same app; a configuration group can apply a level across OUs.
• Apps are chosen individually. Gmail, Drive and Docs, Calendar, Vault, the Admin console and many others can each get their own assignment; levels can also cover some third-party and private web apps.
• Desktop and mobile apps are covered. Google's help pages describe options for applying levels to mobile and desktop apps as well as browsers; check the current settings before relying on one.
• Blocked users see a message. Administrators can write a custom message explaining what to do, such as "Use a company laptop or contact the IT helpdesk".

Owen plans a first set of assignments that matches how Birchline actually works.

The Stores row reflects a deliberate choice. Floor staff sign in only on shared store tablets, which stay in the store, so Company network is a simple and reliable test. If a store's internet provider changes its IP addresses, though, every tablet in that store will be blocked. Owen adds a step to the store network change procedure: update the Company network level before the new connection goes live.

Monitor mode first

Turning on a level for 1,100 people without testing it is how outages happen. Google's help pages describe a way to run CAA assignments in a monitor mode, in which requests that would have been blocked are logged but allowed, so administrators can see the effect before enforcing. Where monitor mode is available for an assignment, Owen uses it for two weeks per wave and reviews the results in the audit logs (lesson 8), looking for the people and devices that would have been blocked and fixing each cause.

A short calculation from the pilot's two-week monitor log shows why. Owen counts, for each would-have-been-blocked request, the reason it failed, and estimates how many people in the February wave would be affected if nothing changed.

# Would-have-been-blocked requests from the pilot's monitor period, by reason.
pilot_people = 14
blocked_people = {
    "Endpoint Verification not installed": 3,
    "Encryption status not yet synced": 1,
    "Personal laptop used at home": 2,
    "Hotel network abroad": 0,
}
head_office = 230
for reason, n in blocked_people.items():
    share = n / pilot_people
    print(f"{reason:38} {n:>2} of {pilot_people} -> about {round(share * head_office)} in head office")
total = sum(blocked_people.values())
print(f"Total: {total} of {pilot_people} pilot users would have been blocked")

Endpoint Verification not installed     3 of 14 -> about 49 in head office
Encryption status not yet synced        1 of 14 -> about 16 in head office
Personal laptop used at home            2 of 14 -> about 33 in head office
Hotel network abroad                    0 of 14 -> about 0 in head office
Total: 6 of 14 pilot users would have been blocked

These figures are a projection from a planned pilot, so the real numbers will differ, but the pattern is typical. Most would-be blocks come from missing software, which Owen can fix before enforcement by deploying Endpoint Verification everywhere. The two people using personal laptops raise a policy question for Teresa rather than a technical one: either they get company laptops, or the level for their OU allows Company network as well.

Order of rollout

Sofia recommends an order that starts where the risk is highest and the number of people is smallest.

• First, the Admin console. Only about a dozen admin accounts are affected, and a stolen admin session is the worst case. Keep one super admin account outside the assignment as a break-glass path, recorded and watched, so a misconfigured level cannot lock out every administrator.
• Second, Vault. Few people use it, and it holds everything.
• Third, Drive and Gmail for Finance and People and culture, the OUs with the most sensitive data.
• Fourth, everyone else, wave by wave, after monitor mode.

The break-glass point deserves emphasis. CAA applied to the Admin console can lock out the very people who would fix it. Google's guidance is to keep a super admin able to reach the console in an emergency; Birchline's sealed emergency account, tested quarterly, is that path.

Privacy and fairness

Device signals include information about personal devices when staff use them for work. US law gives employers wide latitude on company systems, but several states require notice of electronic monitoring, and transparency builds trust. Teresa adds a paragraph to the acceptable use policy explaining that Endpoint Verification reports device security status, not browsing or files, and that personal computers are not required.

How CAA fits with the other layers

Context-aware access is easy to over-trust. It decides whether a request may reach an app; it does not decide what the person may do once inside. A finance manager on a managed laptop can still share a payroll file with the wrong person, which is a job for sharing settings and data loss prevention (lesson 4). An attacker who steals a session cookie from a managed laptop arrives with that laptop's context, which is why session length and alerts still matter. And CAA does nothing for mail that has already left the organization. Sofia draws the boundary for Owen in one sentence: CAA narrows the doors; it does not watch the rooms.

Travel and other exceptions

Exceptions arrive within days of any rollout. A buyer travels to a trade show in Europe and is blocked by the Allowed countries level. A finance analyst's laptop is being repaired and she needs a loaner. A contractor is on site for a week with his own computer. Each case has a better answer than switching CAA off.

• Travel: a configuration group cfg-caa-travel, assigned a level without the country condition, with the traveler added for the dates of the trip and removed afterwards. The request records the destination and dates, and the group membership change appears in the Admin log.
• Loaner laptops: keep a small pool of company laptops already enrolled and reporting, so a loaner meets the level the moment it is handed over.
• Contractors: contractors sign in with accounts in the Contractors OU, which has its own assignments; they reach shared drives for their project only, from Company network on site, or through a company laptop issued for the engagement.

Owen also writes the custom block message with the helpdesk in mind. It names the reason in plain words, tells people what to try first, and gives the helpdesk extension. A message that just says access denied generates angry calls; a message that says "This app can be used only from a Birchline laptop or a Birchline network. If you are on a Birchline laptop, restart it and try again; otherwise call the IT helpdesk on extension 4357" generates fewer.