Flamingo Raises $4.5M Seed Round

Skip to content

Updated: October 2026

When a server dies, people know who to call. When the finance inbox starts sending new bank details to your suppliers, the questions get harder: who calls the bank, who can shut off email, who tells the client. A cybersecurity tabletop exercise answers those questions in a meeting room, before an attacker forces the answers in real time.

What a Tabletop Exercise Is, and What It Isn't

A tabletop exercise is a guided conversation about an incident that hasn't happened. A facilitator describes a scenario, adds new facts every few minutes, and asks the people in the room what they would do next.

NIST's guide to test, training and exercise programs (SP 800-84, September 2006) puts the boundary plainly: a tabletop exercise "is discussion-based only and does not involve deploying equipment or other resources." Nobody touches a keyboard. Nobody restores a server.

That makes it cheap, and it also defines what it can't prove. A tabletop won't tell you whether last night's backup restores. That's the job of disaster recovery testing, where you run the restore for real. It won't find an open port either, which is what a penetration test is for. What it finds is the gap between the plan on paper and the people who are supposed to follow it.

The output is a short list of those gaps. A missing phone number, an approval nobody owns, a plan stored on the server that the scenario just encrypted.

Who Should Be in the Room

Invite the people named in your incident plan, not everyone who might be curious. For a small company or a single MSP client, that's usually six to ten people:

  • Facilitator. Runs the clock, reads the injects, asks the follow-up questions. Ideally someone who won't be making the decisions.
  • Scribe. NIST calls this role the data collector. Writes down every decision, every "I don't know" and every name that comes up.
  • Decision maker. The owner or an executive who can approve shutting systems down, spending money and calling lawyers.
  • IT lead. Internal IT, the MSP, or both. On a co-managed account, invite both sides.
  • Finance. Essential for any scenario that involves payments.
  • Communications. Whoever would talk to staff, clients and, if it came to it, the press.

The same NIST guide recommends running senior and operational teams separately at first, then together once each group knows its part. For a small team, one combined session is fine. Just keep the executive questions and the technical questions in separate rounds so neither group waits through the other's details.

A 90-Minute Run Sheet

NIST puts a typical tabletop at two to eight hours. That fits a large organization exercising a whole plan. A small team running its first one gets more from 90 minutes on a single scenario than from a day that exhausts everyone by lunch.

TimeSegmentWhat happens
0:00Ground rulesNo-fault discussion, phones down, the facilitator owns the clock. Read the two or three objectives aloud.
0:10Scenario setupThe starting situation: day, time, who is in the office, what just happened.
0:20Inject 1The first new fact. Each role says what they would do in the next 30 minutes.
0:35Inject 2Things get worse. Decisions now cost money or downtime.
0:50Inject 3The curveball: a key person is unreachable, a journalist calls, the attacker makes contact.
1:05HotwashWhat went well, where people hesitated, which parts of the plan failed.
1:20ActionsEvery gap gets an owner and a due date before anyone leaves.

The last ten minutes matter most. A tabletop that ends with "good discussion, everyone" and no owners produces nothing you can check next quarter.

In this r/cybersecurity thread, people who have sat through ransomware tabletops argue about whether they change anything. One reply sums up the case for running them: you don't want the first time you practice to be while everything is on fire.

Four Tabletop Exercise Scenarios With Injects

Each scenario below has a starting situation and three injects. Pick one per session. The question under each is the one that tends to expose the gap.

Ransomware on a Monday Morning

Setup: 7:40 on Monday. Staff report that files on the shared drive have strange extensions and won't open.

Inject 1: The file server and two laptops show the same extension. A text file named "README" sits in every folder.

Inject 2: The backup console shows the backup server was also reached. Last night's job failed. The last good copy is eight days old.

Inject 3: The attackers email the owner directly. They claim they copied client files and give a 72-hour deadline.

The question: who can authorize disconnecting the whole network, and where is the printed copy of the plan and the contact list? If the answer is "on the file server," you've found your first action item. Our breakdown of a ransomware attack walks through how these hours tend to unfold.

Business Email Compromise and a Wire Transfer

Setup: Monday afternoon. A regular supplier calls to ask why last month's invoice is unpaid.

Inject 1: Finance says it was paid on Friday, to the new bank details the supplier emailed two weeks ago.

Inject 2: The supplier never changed banks. The email came from a lookalike domain, and the thread shows your own staff member's replies.

Inject 3: The staff member's mailbox has a rule forwarding every message containing "invoice" to an outside address.

The question: who calls your bank's fraud line, and how fast? Speed decides this one. The FBI's 2025 IC3 report (April 2026) counted 24,768 business email compromise complaints and $3.05 billion in reported losses. Its Recovery Asset Team froze $679 million of $1.16 billion in attempted theft, a 58% success rate, and the report stresses that time is of the essence.

Cloud Account Takeover

Setup: Tuesday. An employee mentions they approved a sign-in prompt on their phone last night that they didn't expect.

Inject 1: Their Microsoft 365 account shows sign-ins from another country, and a new app has been granted access to their mailbox.

Inject 2: Three colleagues received messages from that account with a link to a shared document.

Inject 3: One of those colleagues is the finance manager, and they clicked.

The question: who can revoke sessions, reset credentials and remove the app consent, and do you keep sign-in logs long enough to see where it started?

Your Own Remote Management Tool Turns on You

Setup: Thursday, 16:00. Your RMM or remote access vendor posts a security advisory about an actively exploited flaw.

Inject 1: Your console shows a script you didn't write, queued to every managed device.

Inject 2: Two clients call. Their machines are rebooting.

Inject 3: The vendor recommends taking the server offline. That also removes your main way to reach and fix those machines.

The question: can you shut the tool off and still work, and who tells each client what? The 2021 attack on Kaseya VSA is the real-world model for this one. Our guide to RMM security covers hardening the tool itself.

How to Facilitate Without Turning It Into Theater

A tabletop fails when it becomes a performance for an auditor or a quiz for the IT team. A few habits keep it useful:

  • Keep it no-fault. You're testing the plan, not the people. The moment someone gets blamed, everyone else stops admitting what they don't know.
  • Ask "who" and "how," not "would you." "Would you call the bank?" gets a yes. "Who calls, and what number do they dial?" gets the truth.
  • Hold the clock. If a discussion runs long, note it as an action item and move on.
  • Throw one curveball. The IT lead is on a flight. The owner says "can't we just pay?" A client's lawyer calls. Those are the moments that test a plan.
  • Record decisions, not transcripts. The scribe needs the decision, who made it and what was missing.

You don't have to write scenarios from scratch. CISA publishes Tabletop Exercise Packages (CTEPs) with more than 100 scenarios, including ransomware, insider threat and phishing. Each package comes with objectives, discussion questions, feedback forms and an after-action report template.

For a lighter format, the Backdoors & Breaches card game turns an incident into a round of cards a small team can play in one sitting. This RSAC session plays one live:

Scoring and the After-Action Report

Straight after the last inject, run the hotwash. NIST describes it as a facilitated debrief where participants say what went well, where they need more training and which parts of the plan should change.

Then write it up within a week. The after-action report doesn't need to be long. NIST SP 800-84 asks for background (purpose, objectives, participants, scenario), the observations from the facilitator and scribe, and recommendations for the plan. FEMA's Homeland Security Exercise and Evaluation Program pairs the report with an improvement plan, so every weakness becomes a corrective action.

A simple way to score it: rate each objective as met, partially met or not met, and attach the evidence from the scribe's notes. Then list every action with an owner and a date. Next quarter, check the list before you plan the next scenario.

This r/grc thread asks how to keep tabletops from turning into a box to tick for auditors.

The answer is in the action list. If the same gap shows up two exercises in a row, the tabletop worked and the follow-through didn't.

How Often to Run One

NIST's guidance is to run tabletops periodically, and again after organizational changes, plan updates or new guidance. In practice that means once a year as a floor, plus a session after any of these:

A new MSP or internal IT lead takes over. A key tool changes, such as email, backup or remote management. The person who holds the plan leaves. The company opens a new site or buys another business.

Rotate the scenario each time. Three years of ransomware rehearsals leave a wire fraud call untested. If you carry cyber insurance, check whether the renewal questionnaire asks about exercises, and keep the after-action reports where you can find them. Our overview of cyber insurance requirements covers what carriers look at.

The Short Version

A cybersecurity tabletop exercise is 90 minutes, one scenario, three injects and a list of owners at the end. It tests decisions and the written plan, not systems. Start with ransomware or business email compromise, borrow a CISA package if you'd rather not write your own, and score it against the actions it produces.

If you're still building the plan the exercise will test, our guide to the BC, DR and IR plans explains which one covers what. A full incident response guide for small IT teams is coming next.

Dmytro Koval

Dmytro Koval

Head of Product Engineering

Hi! My name is Dmytro, but everyone calls me Dima. I’m a Software Developer and together with the development team, I help bring Flamingo to life — putting it on its feet from a technical perspective. Originally from Lviv, Ukraine 🇺🇦, but currently based in Spain, where I’ve been enjoying the blend of great weather, culture, and nature. I’m passionate about the mountains and love traveling — exploring new places and cultures really inspires me. These experiences constantly recharge me and give me a fresh perspective, both personally and professionally.

Related Content

Blog Posts

Product Releases

Podcasts

Webinars

Case Studies

Events

Onboarding Guides

Frequently Asked Questions

Cybersecurity Tabletop Exercise

A cybersecurity tabletop exercise is a facilitated discussion where the people named in your incident plan talk through a simulated attack, such as ransomware or business email compromise. A facilitator adds new facts every few minutes and asks who does what next. Nobody touches systems; NIST SP 800-84 describes tabletops as discussion-based only. The output is a list of gaps in the plan, each with an owner.
NIST SP 800-84 puts a typical tabletop exercise at two to eight hours, which suits a large organization exercising a whole plan. A small team running its first session gets good results from 90 minutes on one scenario: ten minutes of ground rules, ten of setup, three 15-minute injects, a 15-minute hotwash and ten minutes to assign owners and due dates.
Run one at least once a year, and again after a big change: a new MSP or IT lead, a new email, backup or remote management tool, the departure of the person who holds the plan, or a new site or acquisition. NIST recommends exercising periodically and after organizational changes or plan updates. Rotate the scenario each time so every part of the plan gets tested.
Background (purpose, objectives, participants and the scenario), the observations from the facilitator and scribe, and recommendations for the plan, as NIST SP 800-84 describes. Score each objective as met, partially met or not met with evidence from the notes, then add an improvement plan where every action has an owner and a due date. Keep it to about a page and write it within a week.

MSP AI Agents

On a five-person desk, reported deployments show $78,000 to $130,000 in annual direct labor savings, roughly 30% fewer escalations, and 15% to 20% better SLA compliance. Broader MSP adoption data adds ticket handling time cut by 45% and five to 12 points of margin, all from reclaimed capacity rather than headcount cuts.
Yes. In production MSP shops today, 10% to 25% of tickets close before a human opens them. Thread alone has processed 173 million tickets across 750-plus MSP partners at 96% triage accuracy, handing back 490,000-plus technician hours. Agents own the low-risk, high-volume work (password resets, MFA enrollment, known installs, onboarding and offboarding) and flag anything that touches production data or needs judgment for a human to take.

About OpenFrame

OpenFrame isn't built to plug into your stack. It replaces it. Instead of duct-taping a dozen tools together (RMM, MDM, SIEM, patching, remote access, each its own login and bill), we bundle it into one unified platform: RMM, MDM, monitoring, automation, remote access, patch management, security monitoring, and ticketing, plus built-in AI copilots. So "does it integrate with X?" usually means: you won't need X anymore.
Most platforms give you one piece and expect you to bolt the rest on. OpenFrame unifies the whole stack in one place, with AI copilots built in. Fewer logins, fewer bills, less duct tape.
In the cloud, on US soil. Your data stays stateside.
Both. It's built for MSPs and MSSPs alike.