diff --git a/.github/workflows/ci.yml b/.github/workflows/ci.yml
index 9f4f4e1..897e774 100644
--- a/.github/workflows/ci.yml
+++ b/.github/workflows/ci.yml
@@ -22,5 +22,6 @@ jobs:
       - run: bun ci
       - run: bun run lint
       - run: bun run typecheck
+      - run: bun run test:scripts
       - run: bun run compile
       - run: xvfb-run -a bun run test:coverage
diff --git a/.github/workflows/create-draft-release.yml b/.github/workflows/create-draft-release.yml
new file mode 100644
index 0000000..db23d1f
--- /dev/null
+++ b/.github/workflows/create-draft-release.yml
@@ -0,0 +1,39 @@
+name: Create Draft Release
+
+on:
+  pull_request:
+    types:
+      - closed
+
+permissions: {}
+
+jobs:
+  create-draft-release:
+    if: github.event.pull_request.merged == true && contains(github.event.pull_request.labels.*.name, 'release')
+    runs-on: ubuntu-latest
+    timeout-minutes: 5
+    permissions:
+      contents: write
+    steps:
+      - uses: actions/checkout@df4cb1c069e1874edd31b4311f1884172cec0e10 # v6.0.3
+        with:
+          ref: ${{ github.event.repository.default_branch }}
+          persist-credentials: true
+      - name: Extract release details
+        id: release-details
+        run: |
+          set -euo pipefail
+          version="$(node scripts/prepare-release.mjs current-version)"
+          echo "version=$version" >> "$GITHUB_OUTPUT"
+          node scripts/prepare-release.mjs release-notes > draft-release-notes.md
+      - name: Create draft release
+        env:
+          GH_TOKEN: ${{ github.token }}
+          VERSION: ${{ steps.release-details.outputs.version }}
+        run: |
+          set -euo pipefail
+          gh release create "$VERSION" \
+            --draft \
+            --title "$VERSION" \
+            --notes-file draft-release-notes.md \
+            --target "$(git rev-parse HEAD)"
diff --git a/.github/workflows/labeler.yml b/.github/workflows/labeler.yml
index 30408da..6399c09 100644
--- a/.github/workflows/labeler.yml
+++ b/.github/workflows/labeler.yml
@@ -31,5 +31,5 @@ jobs:
     steps:
       - uses: agilepathway/label-checker@c3d16ad512e7cea5961df85ff2486bb774caf3c5 # v1.6.65
         with:
-          one_of: breaking,security,feature,bug,refactor,upgrade,docs,internal
+          one_of: breaking,security,feature,bug,refactor,upgrade,docs,internal,release
           repo_token: ${{ secrets.GITHUB_TOKEN }}
diff --git a/.github/workflows/prepare-release.yml b/.github/workflows/prepare-release.yml
new file mode 100644
index 0000000..bf5f355
--- /dev/null
+++ b/.github/workflows/prepare-release.yml
@@ -0,0 +1,63 @@
+name: Prepare Release
+
+on:
+  workflow_dispatch:
+    inputs:
+      bump:
+        description: Release bump
+        required: true
+        type: choice
+        options:
+          - patch
+          - minor
+          - major
+      date:
+        description: Release date in YYYY-MM-DD format. Defaults to today.
+        required: false
+        type: string
+
+permissions: {}
+
+jobs:
+  prepare-release:
+    runs-on: ubuntu-latest
+    timeout-minutes: 5
+    permissions:
+      contents: write
+      issues: write
+      pull-requests: write
+    steps:
+      - uses: actions/checkout@df4cb1c069e1874edd31b4311f1884172cec0e10 # v6.0.3
+        with:
+          token: ${{ secrets.FASTAPI_VSCODE_LATEST_CHANGES }} # zizmor: ignore[secrets-outside-env]
+          persist-credentials: true
+      - name: Prepare release
+        env:
+          BUMP: ${{ inputs.bump }}
+          DATE: ${{ inputs.date }}
+        run: node scripts/prepare-release.mjs prepare "$BUMP" "$DATE"
+      - name: Get release version
+        id: release-version
+        run: |
+          set -euo pipefail
+          version="$(node scripts/prepare-release.mjs current-version)"
+          echo "version=$version" >> "$GITHUB_OUTPUT"
+      - name: Create release pull request
+        env:
+          GH_TOKEN: ${{ secrets.FASTAPI_VSCODE_LATEST_CHANGES }}
+          VERSION: ${{ steps.release-version.outputs.version }}
+        run: |
+          set -euo pipefail
+          branch="release-${VERSION}-${GITHUB_RUN_ID}-${GITHUB_RUN_ATTEMPT}"
+          git config user.name "github-actions[bot]"
+          git config user.email "github-actions[bot]@users.noreply.github.com"
+          git switch -c "$branch"
+          git add package.json CHANGELOG.md
+          git commit -m "🔖 Release version ${VERSION}"
+          git push --set-upstream origin "$branch"
+          gh pr create \
+            --base main \
+            --head "$branch" \
+            --title "🔖 Release version ${VERSION}" \
+            --body "Prepare release ${VERSION}." \
+            --label release
diff --git a/CHANGELOG.md b/CHANGELOG.md
index 8795296..151eb89 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -2,10 +2,6 @@
 
 ## Latest Changes
 
-### Internal
-
-* 🔖 Release version 0.2.2. PR [#169](https://github.com/fastapi/fastapi-vscode/pull/169) by [@savannahostrowski](https://github.com/savannahostrowski).
-
 ## 0.2.2
 
 ### Fixes
diff --git a/package.json b/package.json
index 458a5fd..256c5c6 100644
--- a/package.json
+++ b/package.json
@@ -334,8 +334,9 @@
     "watch": "bun run esbuild.js --watch",
     "package": "vsce package",
     "publish:marketplace": "vsce publish",
-    "lint": "biome check --write --unsafe --no-errors-on-unmatched --files-ignore-unknown=true src/",
-    "test": "bun run compile && vscode-test",
+    "lint": "biome check --write --unsafe --no-errors-on-unmatched --files-ignore-unknown=true src/ scripts/",
+    "test": "bun run test:scripts && bun run compile && vscode-test",
+    "test:scripts": "node --test scripts/*.test.mjs",
     "test:coverage": "bash scripts/test-coverage.sh",
     "test:web": "bun run compile && bunx @vscode/test-web --extensionDevelopmentPath=. --browserType=none",
     "typecheck": "tsc --noEmit",
@@ -366,7 +367,7 @@
     "web-tree-sitter": "^0.26.3"
   },
   "lint-staged": {
-    "**/*.{ts,js,json}": [
+    "**/*.{ts,js,mjs,json}": [
       "biome check --write"
     ]
   }
diff --git a/scripts/prepare-release.mjs b/scripts/prepare-release.mjs
new file mode 100644
index 0000000..18e70d1
--- /dev/null
+++ b/scripts/prepare-release.mjs
@@ -0,0 +1,184 @@
+/**
+ * Prepare a release by bumping the version in package.json and rolling CHANGELOG.md.
+ */
+
+import { readFileSync, writeFileSync } from "node:fs"
+import { dirname, join } from "node:path"
+import { fileURLToPath, pathToFileURL } from "node:url"
+
+const ROOT = join(dirname(fileURLToPath(import.meta.url)), "..")
+const VERSION_FILE =
+  process.env.PREPARE_RELEASE_VERSION_FILE ?? join(ROOT, "package.json")
+const CHANGELOG_FILE =
+  process.env.PREPARE_RELEASE_RELEASE_NOTES_FILE ?? join(ROOT, "CHANGELOG.md")
+
+const RELEASE_NOTES_HEADER = "# Release Notes\n\n"
+const LATEST_CHANGES_HEADER = "## Latest Changes"
+
+// Matches the single top-level `"version": "X.Y.Z"` in package.json.
+const VERSION_PATTERN =
+  /^(?<indent>\s*)"version":\s*"(?<version>\d+\.\d+\.\d+)"/m
+// Matches any version section heading, with or without a date suffix,
+// e.g. `## 0.2.2` or `## 0.2.2 (2026-06-16)`.
+const VERSION_HEADING_PATTERN = /^## \d+\.\d+\.\d+(?: \([^)]+\))?\s*$/m
+
+function parseVersion(version) {
+  if (!/^\d+\.\d+\.\d+$/.test(version)) {
+    throw new Error(`Invalid version: '${version}'. Expected format: X.Y.Z`)
+  }
+  return version.split(".").map(Number)
+}
+
+function bumpVersion(version, bump) {
+  const [major, minor, patch] = parseVersion(version)
+  if (bump === "major") return `${major + 1}.0.0`
+  if (bump === "minor") return `${major}.${minor + 1}.0`
+  if (bump === "patch") return `${major}.${minor}.${patch + 1}`
+  throw new Error(`Invalid bump: '${bump}'. Expected major, minor, or patch.`)
+}
+
+function getCurrentVersion(content) {
+  const matches = [...content.matchAll(new RegExp(VERSION_PATTERN, "gm"))]
+  if (matches.length !== 1) {
+    throw new Error(
+      `Expected exactly one "version" assignment in package.json, found ${matches.length}`,
+    )
+  }
+  return matches[0].groups.version
+}
+
+function updateVersionFile(content, version) {
+  const current = getCurrentVersion(content)
+  if (compareVersions(parseVersion(version), parseVersion(current)) <= 0) {
+    throw new Error(
+      `New version ${version} must be greater than current version ${current}`,
+    )
+  }
+  return content.replace(VERSION_PATTERN, `$<indent>"version": "${version}"`)
+}
+
+function compareVersions(a, b) {
+  for (let i = 0; i < 3; i++) {
+    if (a[i] !== b[i]) return a[i] - b[i]
+  }
+  return 0
+}
+
+function updateChangelog(content, version, date) {
+  if (!content.startsWith(RELEASE_NOTES_HEADER)) {
+    throw new Error(
+      `CHANGELOG.md must start with '${RELEASE_NOTES_HEADER.trim()}'`,
+    )
+  }
+  if (versionHeadingRegex(version).test(content)) {
+    throw new Error(`CHANGELOG.md already contains a section for ${version}`)
+  }
+
+  const latestHeader = `${RELEASE_NOTES_HEADER}${LATEST_CHANGES_HEADER}\n`
+  if (!content.startsWith(latestHeader)) {
+    throw new Error(`CHANGELOG.md must start with '${latestHeader.trim()}'`)
+  }
+
+  return content.replace(
+    latestHeader,
+    `${RELEASE_NOTES_HEADER}${LATEST_CHANGES_HEADER}\n\n## ${version} (${date})\n`,
+  )
+}
+
+function getReleaseNotesBody(content, version) {
+  const match = versionHeadingRegex(version).exec(content)
+  if (!match) {
+    throw new Error(`Could not find CHANGELOG section for ${version}`)
+  }
+
+  const rest = content.slice(match.index + match[0].length)
+  const next = VERSION_HEADING_PATTERN.exec(rest)
+  const body = (next ? rest.slice(0, next.index) : rest).trim()
+  if (!body) {
+    throw new Error(`CHANGELOG section for ${version} is empty`)
+  }
+  return `${body}\n`
+}
+
+function versionHeadingRegex(version) {
+  return new RegExp(`^## ${escapeRegExp(version)}(?: \\([^)]+\\))?\\s*$`, "m")
+}
+
+function escapeRegExp(value) {
+  return value.replace(/[.*+?^${}()|[\]\\]/g, "\\$&")
+}
+
+/** Validates a YYYY-MM-DD date, or returns today (UTC) when empty. */
+function resolveDate(input) {
+  if (!input) return new Date().toISOString().slice(0, 10)
+  const parsed = new Date(`${input}T00:00:00Z`)
+  if (
+    Number.isNaN(parsed.getTime()) ||
+    parsed.toISOString().slice(0, 10) !== input
+  ) {
+    throw new Error(`Invalid date: '${input}'. Expected format: YYYY-MM-DD`)
+  }
+  return input
+}
+
+function commandPrepare(bump, dateArg) {
+  if (!bump) throw new Error("Usage: prepare <patch|minor|major> [YYYY-MM-DD]")
+  const date = resolveDate(dateArg)
+  const pkg = readFileSync(VERSION_FILE, "utf8")
+  const changelog = readFileSync(CHANGELOG_FILE, "utf8")
+  const version = bumpVersion(getCurrentVersion(pkg), bump)
+
+  writeFileSync(VERSION_FILE, updateVersionFile(pkg, version))
+  writeFileSync(CHANGELOG_FILE, updateChangelog(changelog, version, date))
+  process.stdout.write(`Prepared release ${version} (${date})\n`)
+}
+
+function commandCurrentVersion() {
+  process.stdout.write(
+    `${getCurrentVersion(readFileSync(VERSION_FILE, "utf8"))}\n`,
+  )
+}
+
+function commandReleaseNotes() {
+  const version = getCurrentVersion(readFileSync(VERSION_FILE, "utf8"))
+  process.stdout.write(
+    getReleaseNotesBody(readFileSync(CHANGELOG_FILE, "utf8"), version),
+  )
+}
+
+function main(argv) {
+  const [command, arg, arg2] = argv
+  try {
+    if (command === "prepare") commandPrepare(arg, arg2)
+    else if (command === "current-version") commandCurrentVersion()
+    else if (command === "release-notes") commandReleaseNotes()
+    else {
+      process.stderr.write(
+        "Usage: prepare-release.mjs <prepare <bump>|current-version|release-notes>\n",
+      )
+      process.exit(2)
+    }
+  } catch (error) {
+    process.stderr.write(`${error.message}\n`)
+    process.exit(1)
+  }
+}
+
+// Run as a CLI only when executed directly, so tests can import the pure
+// functions below without triggering file writes.
+if (
+  process.argv[1] &&
+  import.meta.url === pathToFileURL(process.argv[1]).href
+) {
+  main(process.argv.slice(2))
+}
+
+export {
+  parseVersion,
+  bumpVersion,
+  getCurrentVersion,
+  updateVersionFile,
+  updateChangelog,
+  getReleaseNotesBody,
+  resolveDate,
+}
diff --git a/scripts/prepare-release.test.mjs b/scripts/prepare-release.test.mjs
new file mode 100644
index 0000000..2975afc
--- /dev/null
+++ b/scripts/prepare-release.test.mjs
@@ -0,0 +1,263 @@
+import assert from "node:assert/strict"
+import { execFileSync } from "node:child_process"
+import { mkdtempSync, readFileSync, rmSync, writeFileSync } from "node:fs"
+import { tmpdir } from "node:os"
+import { join } from "node:path"
+import { test } from "node:test"
+import { fileURLToPath } from "node:url"
+import {
+  bumpVersion,
+  getCurrentVersion,
+  getReleaseNotesBody,
+  parseVersion,
+  resolveDate,
+  updateChangelog,
+  updateVersionFile,
+} from "./prepare-release.mjs"
+
+const SCRIPT = fileURLToPath(new URL("./prepare-release.mjs", import.meta.url))
+
+// Runs the CLI in a throwaway dir with the version/changelog files pointed at
+// temp copies, so nothing touches the real repo files. Returns { stdout }.
+function withCli(versionContent, changelogContent, run) {
+  const dir = mkdtempSync(join(tmpdir(), "prepare-release-"))
+  try {
+    const versionFile = join(dir, "package.json")
+    const changelogFile = join(dir, "CHANGELOG.md")
+    if (versionContent !== null) writeFileSync(versionFile, versionContent)
+    if (changelogContent !== null)
+      writeFileSync(changelogFile, changelogContent)
+    const stdout = (args) =>
+      execFileSync("node", [SCRIPT, ...args], {
+        encoding: "utf8",
+        env: {
+          ...process.env,
+          PREPARE_RELEASE_VERSION_FILE: versionFile,
+          PREPARE_RELEASE_RELEASE_NOTES_FILE: changelogFile,
+        },
+      })
+    return run({ versionFile, changelogFile, stdout })
+  } finally {
+    rmSync(dir, { recursive: true, force: true })
+  }
+}
+
+const PACKAGE_JSON = `{
+  "name": "fastapi",
+  "version": "0.2.2",
+  "publisher": "FastAPILabs"
+}
+`
+
+const CHANGELOG = `# Release Notes
+
+## Latest Changes
+
+### Fixes
+
+* 🐛 Fix a thing. PR [#1](https://example.com/1).
+
+## 0.2.1
+
+### Docs
+
+* 📝 Document a thing. PR [#2](https://example.com/2).
+`
+
+test("parseVersion accepts X.Y.Z and rejects anything else", () => {
+  assert.deepEqual(parseVersion("1.2.3"), [1, 2, 3])
+  assert.throws(() => parseVersion("1.2"), /Invalid version/)
+  assert.throws(() => parseVersion("1.2.3-rc1"), /Invalid version/)
+  assert.throws(() => parseVersion("v1.2.3"), /Invalid version/)
+})
+
+test("bumpVersion increments the right component and resets lower ones", () => {
+  assert.equal(bumpVersion("0.2.2", "patch"), "0.2.3")
+  assert.equal(bumpVersion("0.2.2", "minor"), "0.3.0")
+  assert.equal(bumpVersion("0.2.2", "major"), "1.0.0")
+  assert.throws(() => bumpVersion("0.2.2", "huge"), /Invalid bump/)
+})
+
+test("getCurrentVersion extracts the single version field", () => {
+  assert.equal(getCurrentVersion(PACKAGE_JSON), "0.2.2")
+})
+
+test("getCurrentVersion requires exactly one version field", () => {
+  assert.throws(() => getCurrentVersion(`{ "name": "x" }`), /found 0/)
+  const twoVersions = `{\n  "version": "1.0.0",\n  "version": "2.0.0"\n}\n`
+  assert.throws(() => getCurrentVersion(twoVersions), /found 2/)
+})
+
+test("updateVersionFile replaces the version and preserves the rest", () => {
+  const updated = updateVersionFile(PACKAGE_JSON, "0.2.3")
+  assert.match(updated, /"version": "0.2.3"/)
+  assert.match(updated, /"name": "fastapi"/)
+  assert.match(updated, /"publisher": "FastAPILabs"/)
+  assert.doesNotMatch(updated, /0\.2\.2/)
+})
+
+test("updateVersionFile rejects a non-newer version", () => {
+  assert.throws(
+    () => updateVersionFile(PACKAGE_JSON, "0.2.2"),
+    /must be greater/,
+  )
+  assert.throws(
+    () => updateVersionFile(PACKAGE_JSON, "0.2.1"),
+    /must be greater/,
+  )
+})
+
+test("updateChangelog inserts a dated heading under Latest Changes", () => {
+  const updated = updateChangelog(CHANGELOG, "0.3.0", "2026-06-16")
+  assert.match(
+    updated,
+    /## Latest Changes\n\n## 0\.3\.0 \(2026-06-16\)\n\n### Fixes/,
+  )
+  // Existing content is preserved below the new section.
+  assert.match(updated, /## 0\.2\.1\n\n### Docs/)
+})
+
+test("updateChangelog rejects a version that already has a section", () => {
+  // 0.2.1 exists as a plain (undated) heading already.
+  assert.throws(
+    () => updateChangelog(CHANGELOG, "0.2.1", "2026-06-16"),
+    /already contains a section/,
+  )
+})
+
+test("updateChangelog requires the expected header", () => {
+  assert.throws(
+    () => updateChangelog("## Latest Changes\n", "0.3.0", "2026-06-16"),
+    /must start with/,
+  )
+})
+
+test("getReleaseNotesBody extracts a dated section", () => {
+  const content = `# Release Notes
+
+## Latest Changes
+
+## 0.3.0 (2026-06-16)
+
+### Fixes
+
+* 🐛 Fixed it. PR [#9](https://example.com/9).
+
+## 0.2.2
+
+### Docs
+
+* old
+`
+  assert.equal(
+    getReleaseNotesBody(content, "0.3.0"),
+    "### Fixes\n\n* 🐛 Fixed it. PR [#9](https://example.com/9).\n",
+  )
+})
+
+test("getReleaseNotesBody extracts a plain (undated) section", () => {
+  assert.equal(
+    getReleaseNotesBody(CHANGELOG, "0.2.1"),
+    "### Docs\n\n* 📝 Document a thing. PR [#2](https://example.com/2).\n",
+  )
+})
+
+test("getReleaseNotesBody keeps non-version h2 content inside a section", () => {
+  const content = `# Release Notes
+
+## Latest Changes
+
+## 0.3.0 (2026-06-16)
+
+### Fixes
+
+* 🐛 Fixed it.
+
+## Acknowledgements
+
+Thanks everyone.
+
+## 0.2.2
+
+* old
+`
+  const body = getReleaseNotesBody(content, "0.3.0")
+  assert.match(body, /## Acknowledgements/)
+  assert.match(body, /Thanks everyone\./)
+  assert.doesNotMatch(body, /old/)
+})
+
+test("getReleaseNotesBody requires the version section to exist", () => {
+  assert.throws(() => getReleaseNotesBody(CHANGELOG, "9.9.9"), /Could not find/)
+})
+
+test("getReleaseNotesBody rejects an empty section", () => {
+  const content = `# Release Notes
+
+## Latest Changes
+
+## 0.3.0 (2026-06-16)
+
+## 0.2.2
+
+* old
+`
+  assert.throws(() => getReleaseNotesBody(content, "0.3.0"), /is empty/)
+})
+
+test("resolveDate passes through a valid date", () => {
+  assert.equal(resolveDate("2026-06-16"), "2026-06-16")
+})
+
+test("resolveDate defaults to a YYYY-MM-DD date when empty", () => {
+  assert.match(resolveDate(""), /^\d{4}-\d{2}-\d{2}$/)
+  assert.match(resolveDate(undefined), /^\d{4}-\d{2}-\d{2}$/)
+})
+
+test("resolveDate rejects malformed or impossible dates", () => {
+  assert.throws(() => resolveDate("2026-13-40"), /Invalid date/)
+  assert.throws(() => resolveDate("06-16-2026"), /Invalid date/)
+  assert.throws(() => resolveDate("not-a-date"), /Invalid date/)
+})
+
+// --- CLI end-to-end (run against temp files; never touches the repo) ---
+
+test("CLI prepare updates both files and prints the new version", () => {
+  const pkg = `{\n  "name": "x",\n  "version": "0.2.2"\n}\n`
+  const changelog =
+    "# Release Notes\n\n## Latest Changes\n\n### Fixes\n\n* Fix something.\n"
+  withCli(pkg, changelog, ({ versionFile, changelogFile, stdout }) => {
+    const out = stdout(["prepare", "patch", "2026-06-16"])
+    assert.match(out, /Prepared release 0\.2\.3 \(2026-06-16\)/)
+    assert.match(readFileSync(versionFile, "utf8"), /"version": "0.2.3"/)
+    assert.match(
+      readFileSync(changelogFile, "utf8"),
+      /## 0\.2\.3 \(2026-06-16\)/,
+    )
+  })
+})
+
+test("CLI prepare reads file paths from PREPARE_RELEASE_* env vars", () => {
+  const pkg = `{\n  "version": "1.4.9"\n}\n`
+  const changelog = "# Release Notes\n\n## Latest Changes\n\n* something\n"
+  withCli(pkg, changelog, ({ versionFile, stdout }) => {
+    stdout(["prepare", "minor"])
+    assert.match(readFileSync(versionFile, "utf8"), /"version": "1.5.0"/)
+  })
+})
+
+test("CLI current-version prints the version", () => {
+  const pkg = `{\n  "version": "0.2.2"\n}\n`
+  withCli(pkg, null, ({ stdout }) => {
+    assert.equal(stdout(["current-version"]), "0.2.2\n")
+  })
+})
+
+test("CLI release-notes prints the current version's section body", () => {
+  const pkg = `{\n  "version": "0.2.2"\n}\n`
+  const changelog =
+    "# Release Notes\n\n## Latest Changes\n\n## 0.2.2\n\n### Fixes\n\n* Fix it.\n\n## 0.2.1\n\n* old\n"
+  withCli(pkg, changelog, ({ stdout }) => {
+    assert.equal(stdout(["release-notes"]), "### Fixes\n\n* Fix it.\n")
+  })
+})