diff --git a/ee/tools/license/README.md b/ee/tools/license/README.md
new file mode 100644
index 0000000000..f2ed5ed6f1
--- /dev/null
+++ b/ee/tools/license/README.md
@@ -0,0 +1,56 @@
+# Fleet license key generation
+
+This directory contains the Node script for generating Fleet license keys.
+
+## Usage
+
+### Setup
+
+Install the JS dependencies:
+
+```sh
+yarn
+```
+
+Put the private key and passphrase into files (avoid using shell commands to prevent secrets from leaking into shell history). Speak to @zwass or @mikermcneil if you need to get access to these secrets.
+
+```sh
+nano key.pem
+nano passphrase.txt
+```
+
+### Generate a key
+
+Run `./license.js generate` to generate a key. For example:
+
+````sh
+./license.js generate --private-key key.pem --key-passphrase passphrase.txt --expiration 2022-01-01 --customer test --devices 100 --note 'for development only'
+eyJhbGciOiJFUzI1NiIsInR5cCI6IkpXVCJ9.eyJpc3MiOiJGbGVldCBEZXZpY2UgTWFuYWdlbWVudCBJbmMuIiwiZXhwIjoxNjQwOTk1MjAwLCJzdWIiOiJkZXZlbG9wbWVudCIsImRldmljZXMiOjEwMCwibm90ZSI6ImZvciBkZXZlbG9wbWVudCBvbmx5IiwidGllciI6ImJhc2ljIiwiaWF0IjoxNjIyNDI2NTg2fQ.WmZ0kG4seW3IrNvULCHUPBSfFdqj38A_eiXdV_DFunMHechjHbkwtfkf1J6JQJoDyqn8raXpgbdhafDwv3rmDw
+```
+
+See `./license.js generate --help` for more details on arguments.
+
+## Key format
+
+License keys are JWTs signed with the `ES256` method.
+
+Check the contents of a key with [https://jwt.io/](https://jwt.io/).
+
+The key generated above contains the following payload:
+
+```json
+{
+  "iss": "Fleet Device Management Inc.",
+  "exp": 1640995200,
+  "sub": "development",
+  "devices": 100,
+  "note": "for development only",
+  "tier": "basic",
+  "iat": 1622426586
+}
+````
+
+- `devices` refers to the number of licensed devices.
+- `note` includes any additional note about the terms of the license.
+- `tier` is the license Tier: currently `basic` = paid, `core` = free (though we do not plan to issue license keys for `core`)
+- Other claims use the meanings [described in the JWT specification](https://datatracker.ietf.org/doc/html/rfc7519#section-4.1).
diff --git a/ee/tools/license/license.js b/ee/tools/license/license.js
new file mode 100755
index 0000000000..63e2cceae6
--- /dev/null
+++ b/ee/tools/license/license.js
@@ -0,0 +1,102 @@
+#!/usr/bin/env node
+
+import fs from "fs";
+
+import jwt from "jsonwebtoken";
+import yargs from "yargs";
+import { hideBin } from "yargs/helpers";
+
+// Generate the JWT license key using the provided options.
+const generate = (argv) => {
+  const {
+    privateKey: privateKeyPath,
+    keyPassphrase: keyPassphrasePath,
+    expiration,
+    customer,
+    devices,
+    note,
+    tier,
+  } = argv;
+
+  const unixExpiration = Math.floor(expiration / 1000);
+
+  const privateKey = fs.readFileSync(privateKeyPath);
+  const keyPassphrase = fs.readFileSync(keyPassphrasePath).toString().trim();
+
+  const licensePayload = {
+    iss: "Fleet Device Management Inc.",
+    exp: unixExpiration,
+    sub: customer,
+    devices,
+    note,
+    tier,
+  };
+  console.log(
+    jwt.sign(
+      licensePayload,
+      { key: privateKey, passphrase: keyPassphrase },
+      { algorithm: "ES256" }
+    )
+  );
+};
+
+// Like Date.parse but error if date cannot be parsed.
+const coerceDate = (str) => {
+  const date = Date.parse(str);
+  if (isNaN(date)) {
+    throw new Error(`'${str}' cannot be parsed as date`);
+  }
+  return date;
+};
+
+yargs(hideBin(process.argv))
+  .command(
+    "generate",
+    "Generate a new license key",
+    (cmd) => {
+      cmd.option({
+        "private-key": {
+          description: "Path to private key for signing",
+          type: "string",
+          required: true,
+        },
+        "key-passphrase": {
+          description: "Path to file containing private key passphrase",
+          type: "string",
+          required: true,
+        },
+        expiration: {
+          description: "Expiration timestamp of license",
+          type: "string",
+          coerce: coerceDate,
+          required: true,
+        },
+        customer: {
+          description: "Name of customer",
+          type: "string",
+          required: true,
+        },
+        devices: {
+          description: "Licensed device count",
+          type: "number",
+          required: true,
+        },
+        note: {
+          description: "Additional note to add to license",
+          type: "string",
+        },
+        tier: {
+          description: "License tier",
+          default: "basic",
+          type: "string",
+        },
+      });
+    },
+    generate
+  )
+  .demandCommand(1, "Command must be provided") // Require a command
+  .strict() // Reject unknown flags
+  .version(false) // Disable version option
+  .help()
+  .alias("help", "h")
+  .parse();
diff --git a/ee/tools/license/package.json b/ee/tools/license/package.json
new file mode 100644
index 0000000000..7e9e05c9fc
--- /dev/null
+++ b/ee/tools/license/package.json
@@ -0,0 +1,15 @@
+{
+  "name": "fleet-license",
+  "description": "Generate license keys for Fleet.",
+  "version": "0.0.1",
+  "license": "See ../../LICENSE",
+  "main": "license.js",
+  "type": "module",
+  "scripts": {},
+  "dependencies": {},
+  "devDependencies": {
+    "jsonwebtoken": "^8.5.1",
+    "yargs": "^17.0.1"
+  },
+  "private": true
+}
diff --git a/ee/tools/license/yarn.lock b/ee/tools/license/yarn.lock
new file mode 100644
index 0000000000..dcfbe7f0e1
--- /dev/null
+++ b/ee/tools/license/yarn.lock
@@ -0,0 +1,204 @@
+# THIS IS AN AUTOGENERATED FILE. DO NOT EDIT THIS FILE DIRECTLY.
+# yarn lockfile v1
+
+
+ansi-regex@^5.0.0:
+  version "5.0.0"
+  resolved "https://registry.yarnpkg.com/ansi-regex/-/ansi-regex-5.0.0.tgz#388539f55179bf39339c81af30a654d69f87cb75"
+  integrity sha512-bY6fj56OUQ0hU1KjFNDQuJFezqKdrAyFdIevADiqrWHwSlbmBNMHp5ak2f40Pm8JTFyM2mqxkG6ngkHO11f/lg==
+
+ansi-styles@^4.0.0:
+  version "4.3.0"
+  resolved "https://registry.yarnpkg.com/ansi-styles/-/ansi-styles-4.3.0.tgz#edd803628ae71c04c85ae7a0906edad34b648937"
+  integrity sha512-zbB9rCJAT1rbjiVDb2hqKFHNYLxgtk8NURxZ3IZwD3F6NtxbXZQCnnSi1Lkx+IDohdPlFp222wVALIheZJQSEg==
+  dependencies:
+    color-convert "^2.0.1"
+
+buffer-equal-constant-time@1.0.1:
+  version "1.0.1"
+  resolved "https://registry.yarnpkg.com/buffer-equal-constant-time/-/buffer-equal-constant-time-1.0.1.tgz#f8e71132f7ffe6e01a5c9697a4c6f3e48d5cc819"
+  integrity sha1-+OcRMvf/5uAaXJaXpMbz5I1cyBk=
+
+cliui@^7.0.2:
+  version "7.0.4"
+  resolved "https://registry.yarnpkg.com/cliui/-/cliui-7.0.4.tgz#a0265ee655476fc807aea9df3df8df7783808b4f"
+  integrity sha512-OcRE68cOsVMXp1Yvonl/fzkQOyjLSu/8bhPDfQt0e0/Eb283TKP20Fs2MqoPsr9SwA595rRCA+QMzYc9nBP+JQ==
+  dependencies:
+    string-width "^4.2.0"
+    strip-ansi "^6.0.0"
+    wrap-ansi "^7.0.0"
+
+color-convert@^2.0.1:
+  version "2.0.1"
+  resolved "https://registry.yarnpkg.com/color-convert/-/color-convert-2.0.1.tgz#72d3a68d598c9bdb3af2ad1e84f21d896abd4de3"
+  integrity sha512-RRECPsj7iu/xb5oKYcsFHSppFNnsj/52OVTRKb4zP5onXwVF3zVmmToNcOfGC+CRDpfK/U584fMg38ZHCaElKQ==
+  dependencies:
+    color-name "~1.1.4"
+
+color-name@~1.1.4:
+  version "1.1.4"
+  resolved "https://registry.yarnpkg.com/color-name/-/color-name-1.1.4.tgz#c2a09a87acbde69543de6f63fa3995c826c536a2"
+  integrity sha512-dOy+3AuW3a2wNbZHIuMZpTcgjGuLU/uBL/ubcZF9OXbDo8ff4O8yVp5Bf0efS8uEoYo5q4Fx7dY9OgQGXgAsQA==
+
+ecdsa-sig-formatter@1.0.11:
+  version "1.0.11"
+  resolved "https://registry.yarnpkg.com/ecdsa-sig-formatter/-/ecdsa-sig-formatter-1.0.11.tgz#ae0f0fa2d85045ef14a817daa3ce9acd0489e5bf"
+  integrity sha512-nagl3RYrbNv6kQkeJIpt6NJZy8twLB/2vtz6yN9Z4vRKHN4/QZJIEbqohALSgwKdnksuY3k5Addp5lg8sVoVcQ==
+  dependencies:
+    safe-buffer "^5.0.1"
+
+emoji-regex@^8.0.0:
+  version "8.0.0"
+  resolved "https://registry.yarnpkg.com/emoji-regex/-/emoji-regex-8.0.0.tgz#e818fd69ce5ccfcb404594f842963bf53164cc37"
+  integrity sha512-MSjYzcWNOA0ewAHpz0MxpYFvwg6yjy1NG3xteoqz644VCo/RPgnr1/GGt+ic3iJTzQ8Eu3TdM14SawnVUmGE6A==
+
+escalade@^3.1.1:
+  version "3.1.1"
+  resolved "https://registry.yarnpkg.com/escalade/-/escalade-3.1.1.tgz#d8cfdc7000965c5a0174b4a82eaa5c0552742e40"
+  integrity sha512-k0er2gUkLf8O0zKJiAhmkTnJlTvINGv7ygDNPbeIsX/TJjGJZHuh9B2UxbsaEkmlEo9MfhrSzmhIlhRlI2GXnw==
+
+get-caller-file@^2.0.5:
+  version "2.0.5"
+  resolved "https://registry.yarnpkg.com/get-caller-file/-/get-caller-file-2.0.5.tgz#4f94412a82db32f36e3b0b9741f8a97feb031f7e"
+  integrity sha512-DyFP3BM/3YHTQOCUL/w0OZHR0lpKeGrxotcHWcqNEdnltqFwXVfhEBQ94eIo34AfQpo0rGki4cyIiftY06h2Fg==
+
+is-fullwidth-code-point@^3.0.0:
+  version "3.0.0"
+  resolved "https://registry.yarnpkg.com/is-fullwidth-code-point/-/is-fullwidth-code-point-3.0.0.tgz#f116f8064fe90b3f7844a38997c0b75051269f1d"
+  integrity sha512-zymm5+u+sCsSWyD9qNaejV3DFvhCKclKdizYaJUuHA83RLjb7nSuGnddCHGv0hk+KY7BMAlsWeK4Ueg6EV6XQg==
+
+jsonwebtoken@^8.5.1:
+  version "8.5.1"
+  resolved "https://registry.yarnpkg.com/jsonwebtoken/-/jsonwebtoken-8.5.1.tgz#00e71e0b8df54c2121a1f26137df2280673bcc0d"
+  integrity sha512-XjwVfRS6jTMsqYs0EsuJ4LGxXV14zQybNd4L2r0UvbVnSF9Af8x7p5MzbJ90Ioz/9TI41/hTCvznF/loiSzn8w==
+  dependencies:
+    jws "^3.2.2"
+    lodash.includes "^4.3.0"
+    lodash.isboolean "^3.0.3"
+    lodash.isinteger "^4.0.4"
+    lodash.isnumber "^3.0.3"
+    lodash.isplainobject "^4.0.6"
+    lodash.isstring "^4.0.1"
+    lodash.once "^4.0.0"
+    ms "^2.1.1"
+    semver "^5.6.0"
+
+jwa@^1.4.1:
+  version "1.4.1"
+  resolved "https://registry.yarnpkg.com/jwa/-/jwa-1.4.1.tgz#743c32985cb9e98655530d53641b66c8645b039a"
+  integrity sha512-qiLX/xhEEFKUAJ6FiBMbes3w9ATzyk5W7Hvzpa/SLYdxNtng+gcurvrI7TbACjIXlsJyr05/S1oUhZrc63evQA==
+  dependencies:
+    buffer-equal-constant-time "1.0.1"
+    ecdsa-sig-formatter "1.0.11"
+    safe-buffer "^5.0.1"
+
+jws@^3.2.2:
+  version "3.2.2"
+  resolved "https://registry.yarnpkg.com/jws/-/jws-3.2.2.tgz#001099f3639468c9414000e99995fa52fb478304"
+  integrity sha512-YHlZCB6lMTllWDtSPHz/ZXTsi8S00usEV6v1tjq8tOUZzw7DpSDWVXjXDre6ed1w/pd495ODpHZYSdkRTsa0HA==
+  dependencies:
+    jwa "^1.4.1"
+    safe-buffer "^5.0.1"
+
+lodash.includes@^4.3.0:
+  version "4.3.0"
+  resolved "https://registry.yarnpkg.com/lodash.includes/-/lodash.includes-4.3.0.tgz#60bb98a87cb923c68ca1e51325483314849f553f"
+  integrity sha1-YLuYqHy5I8aMoeUTJUgzFISfVT8=
+
+lodash.isboolean@^3.0.3:
+  version "3.0.3"
+  resolved "https://registry.yarnpkg.com/lodash.isboolean/-/lodash.isboolean-3.0.3.tgz#6c2e171db2a257cd96802fd43b01b20d5f5870f6"
+  integrity sha1-bC4XHbKiV82WgC/UOwGyDV9YcPY=
+
+lodash.isinteger@^4.0.4:
+  version "4.0.4"
+  resolved "https://registry.yarnpkg.com/lodash.isinteger/-/lodash.isinteger-4.0.4.tgz#619c0af3d03f8b04c31f5882840b77b11cd68343"
+  integrity sha1-YZwK89A/iwTDH1iChAt3sRzWg0M=
+
+lodash.isnumber@^3.0.3:
+  version "3.0.3"
+  resolved "https://registry.yarnpkg.com/lodash.isnumber/-/lodash.isnumber-3.0.3.tgz#3ce76810c5928d03352301ac287317f11c0b1ffc"
+  integrity sha1-POdoEMWSjQM1IwGsKHMX8RwLH/w=
+
+lodash.isplainobject@^4.0.6:
+  version "4.0.6"
+  resolved "https://registry.yarnpkg.com/lodash.isplainobject/-/lodash.isplainobject-4.0.6.tgz#7c526a52d89b45c45cc690b88163be0497f550cb"
+  integrity sha1-fFJqUtibRcRcxpC4gWO+BJf1UMs=
+
+lodash.isstring@^4.0.1:
+  version "4.0.1"
+  resolved "https://registry.yarnpkg.com/lodash.isstring/-/lodash.isstring-4.0.1.tgz#d527dfb5456eca7cc9bb95d5daeaf88ba54a5451"
+  integrity sha1-1SfftUVuynzJu5XV2ur4i6VKVFE=
+
+lodash.once@^4.0.0:
+  version "4.1.1"
+  resolved "https://registry.yarnpkg.com/lodash.once/-/lodash.once-4.1.1.tgz#0dd3971213c7c56df880977d504c88fb471a97ac"
+  integrity sha1-DdOXEhPHxW34gJd9UEyI+0cal6w=
+
+ms@^2.1.1:
+  version "2.1.3"
+  resolved "https://registry.yarnpkg.com/ms/-/ms-2.1.3.tgz#574c8138ce1d2b5861f0b44579dbadd60c6615b2"
+  integrity sha512-6FlzubTLZG3J2a/NVCAleEhjzq5oxgHyaCU9yYXvcLsvoVaHJq/s5xXI6/XXP6tz7R9xAOtHnSO/tXtF3WRTlA==
+
+require-directory@^2.1.1:
+  version "2.1.1"
+  resolved "https://registry.yarnpkg.com/require-directory/-/require-directory-2.1.1.tgz#8c64ad5fd30dab1c976e2344ffe7f792a6a6df42"
+  integrity sha1-jGStX9MNqxyXbiNE/+f3kqam30I=
+
+safe-buffer@^5.0.1:
+  version "5.2.1"
+  resolved "https://registry.yarnpkg.com/safe-buffer/-/safe-buffer-5.2.1.tgz#1eaf9fa9bdb1fdd4ec75f58f9cdb4e6b7827eec6"
+  integrity sha512-rp3So07KcdmmKbGvgaNxQSJr7bGVSVk5S9Eq1F+ppbRo70+YeaDxkw5Dd8NPN+GD6bjnYm2VuPuCXmpuYvmCXQ==
+
+semver@^5.6.0:
+  version "5.7.1"
+  resolved "https://registry.yarnpkg.com/semver/-/semver-5.7.1.tgz#a954f931aeba508d307bbf069eff0c01c96116f7"
+  integrity sha512-sauaDf/PZdVgrLTNYHRtpXa1iRiKcaebiKQ1BJdpQlWH2lCvexQdX55snPFyK7QzpudqbCI0qXFfOasHdyNDGQ==
+
+string-width@^4.1.0, string-width@^4.2.0:
+  version "4.2.2"
+  resolved "https://registry.yarnpkg.com/string-width/-/string-width-4.2.2.tgz#dafd4f9559a7585cfba529c6a0a4f73488ebd4c5"
+  integrity sha512-XBJbT3N4JhVumXE0eoLU9DCjcaF92KLNqTmFCnG1pf8duUxFGwtP6AD6nkjw9a3IdiRtL3E2w3JDiE/xi3vOeA==
+  dependencies:
+    emoji-regex "^8.0.0"
+    is-fullwidth-code-point "^3.0.0"
+    strip-ansi "^6.0.0"
+
+strip-ansi@^6.0.0:
+  version "6.0.0"
+  resolved "https://registry.yarnpkg.com/strip-ansi/-/strip-ansi-6.0.0.tgz#0b1571dd7669ccd4f3e06e14ef1eed26225ae532"
+  integrity sha512-AuvKTrTfQNYNIctbR1K/YGTR1756GycPsg7b9bdV9Duqur4gv6aKqHXah67Z8ImS7WEz5QVcOtlfW2rZEugt6w==
+  dependencies:
+    ansi-regex "^5.0.0"
+
+wrap-ansi@^7.0.0:
+  version "7.0.0"
+  resolved "https://registry.yarnpkg.com/wrap-ansi/-/wrap-ansi-7.0.0.tgz#67e145cff510a6a6984bdf1152911d69d2eb9e43"
+  integrity sha512-YVGIj2kamLSTxw6NsZjoBxfSwsn0ycdesmc4p+Q21c5zPuZ1pl+NfxVdxPtdHvmNVOQ6XSYG4AUtyt/Fi7D16Q==
+  dependencies:
+    ansi-styles "^4.0.0"
+    string-width "^4.1.0"
+    strip-ansi "^6.0.0"
+
+y18n@^5.0.5:
+  version "5.0.8"
+  resolved "https://registry.yarnpkg.com/y18n/-/y18n-5.0.8.tgz#7f4934d0f7ca8c56f95314939ddcd2dd91ce1d55"
+  integrity sha512-0pfFzegeDWJHJIAmTLRP2DwHjdF5s7jo9tuztdQxAhINCdvS+3nGINqPd00AphqJR/0LhANUS6/+7SCb98YOfA==
+
+yargs-parser@^20.2.2:
+  version "20.2.7"
+  resolved "https://registry.yarnpkg.com/yargs-parser/-/yargs-parser-20.2.7.tgz#61df85c113edfb5a7a4e36eb8aa60ef423cbc90a"
+  integrity sha512-FiNkvbeHzB/syOjIUxFDCnhSfzAL8R5vs40MgLFBorXACCOAEaWu0gRZl14vG8MR9AOJIZbmkjhusqBYZ3HTHw==
+
+yargs@^17.0.1:
+  version "17.0.1"
+  resolved "https://registry.yarnpkg.com/yargs/-/yargs-17.0.1.tgz#6a1ced4ed5ee0b388010ba9fd67af83b9362e0bb"
+  integrity sha512-xBBulfCc8Y6gLFcrPvtqKz9hz8SO0l1Ni8GgDekvBX2ro0HRQImDGnikfc33cgzcYUSncapnNcZDjVFIH3f6KQ==
+  dependencies:
+    cliui "^7.0.2"
+    escalade "^3.1.1"
+    get-caller-file "^2.0.5"
+    require-directory "^2.1.1"
+    string-width "^4.2.0"
+    y18n "^5.0.5"
+    yargs-parser "^20.2.2"