diff --git a/.github/workflows/build.yaml b/.github/workflows/build.yaml
index 0a243e388740..beb2a43a31c0 100644
--- a/.github/workflows/build.yaml
+++ b/.github/workflows/build.yaml
@@ -32,7 +32,7 @@ jobs:
       helm: ${{ steps.filter.outputs.helm }}
     steps:
       - name: Checkout repo
-        uses: actions/checkout@v4
+        uses: actions/checkout@v5
       - name: Check changed files
         uses: dorny/paths-filter@v3
         id: filter
@@ -64,7 +64,7 @@ jobs:
     runs-on: ubuntu-22.04
     timeout-minutes: 5
     steps:
-      - uses: actions/checkout@v4
+      - uses: actions/checkout@v5
       - uses: actions/setup-node@v4
         with:
           node-version-file: .node-version
@@ -82,7 +82,7 @@ jobs:
     needs: changes
     if: needs.changes.outputs.docs == 'true'
     steps:
-      - uses: actions/checkout@v4
+      - uses: actions/checkout@v5
       - uses: actions/setup-node@v4
         with:
           node-version-file: .node-version
@@ -100,7 +100,7 @@ jobs:
     needs: changes
     if: needs.changes.outputs.helm == 'true'
     steps:
-      - uses: actions/checkout@v4
+      - uses: actions/checkout@v5
       - uses: azure/setup-helm@v4
         with:
           token: ${{ secrets.GITHUB_TOKEN }}
@@ -114,7 +114,7 @@ jobs:
     needs: changes
     if: needs.changes.outputs.code == 'true'
     steps:
-      - uses: actions/checkout@v4
+      - uses: actions/checkout@v5
       - uses: actions/setup-node@v4
         with:
           node-version-file: .node-version
@@ -132,7 +132,7 @@ jobs:
     if: needs.changes.outputs.ci == 'true'
     steps:
       - name: Checkout repo
-        uses: actions/checkout@v4
+        uses: actions/checkout@v5
       - name: Check workflow files
         run: |
           bash <(curl https://raw.githubusercontent.com/rhysd/actionlint/main/scripts/download-actionlint.bash) 1.7.1
@@ -146,7 +146,7 @@ jobs:
     needs: changes
     if: needs.changes.outputs.code == 'true'
     steps:
-      - uses: actions/checkout@v4
+      - uses: actions/checkout@v5
       - uses: actions/setup-node@v4
         with:
           node-version-file: .node-version
@@ -169,7 +169,7 @@ jobs:
       CODECOV_TOKEN: ${{ secrets.CODECOV_TOKEN }}
       DISABLE_V8_COMPILE_CACHE: 1
     steps:
-      - uses: actions/checkout@v4
+      - uses: actions/checkout@v5
         with:
           submodules: true
       - run: sudo apt update && sudo apt install -y libkrb5-dev
@@ -231,7 +231,7 @@ jobs:
     needs: [changes, build]
     if: needs.changes.outputs.code == 'true' || needs.changes.outputs.deps == 'true'
     steps:
-      - uses: actions/checkout@v4
+      - uses: actions/checkout@v5
       - run: sudo apt update && sudo apt install -y libkrb5-dev
       - uses: actions/setup-node@v4
         with:
@@ -241,7 +241,7 @@ jobs:
             package-lock.json
             test/package-lock.json
       - run: SKIP_SUBMODULE_DEPS=1 npm ci
-      - uses: actions/download-artifact@v4
+      - uses: actions/download-artifact@v5
         with:
           name: npm-package
       - run: tar -xzf package.tar.gz
@@ -265,7 +265,7 @@ jobs:
     needs: [changes, build]
     if: needs.changes.outputs.code == 'true' || needs.changes.outputs.deps == 'true'
     steps:
-      - uses: actions/checkout@v4
+      - uses: actions/checkout@v5
       - run: sudo apt update && sudo apt install -y libkrb5-dev
       - uses: actions/setup-node@v4
         with:
@@ -275,7 +275,7 @@ jobs:
             package-lock.json
             test/package-lock.json
       - run: SKIP_SUBMODULE_DEPS=1 npm ci
-      - uses: actions/download-artifact@v4
+      - uses: actions/download-artifact@v5
         with:
           name: npm-package
       - run: tar -xzf package.tar.gz
diff --git a/.github/workflows/installer.yaml b/.github/workflows/installer.yaml
index e8b04453dcfc..c33ee0070763 100644
--- a/.github/workflows/installer.yaml
+++ b/.github/workflows/installer.yaml
@@ -30,7 +30,7 @@ jobs:
     runs-on: ubuntu-latest
     steps:
       - name: Checkout repo
-        uses: actions/checkout@v4
+        uses: actions/checkout@v5
 
       - name: Install code-server
         run: ./install.sh
@@ -44,7 +44,7 @@ jobs:
     container: "alpine:3.17"
     steps:
       - name: Checkout repo
-        uses: actions/checkout@v4
+        uses: actions/checkout@v5
 
       - name: Install curl
         run: apk add curl
@@ -67,7 +67,7 @@ jobs:
 
     steps:
       - name: Checkout repo
-        uses: actions/checkout@v4
+        uses: actions/checkout@v5
 
       - name: Install code-server
         run: ./install.sh
diff --git a/.github/workflows/publish.yaml b/.github/workflows/publish.yaml
index 91e320087175..374c35876d41 100644
--- a/.github/workflows/publish.yaml
+++ b/.github/workflows/publish.yaml
@@ -25,7 +25,7 @@ jobs:
     runs-on: ubuntu-latest
     steps:
       - name: Checkout code-server
-        uses: actions/checkout@v4
+        uses: actions/checkout@v5
 
       - name: Install Node.js
         uses: actions/setup-node@v4
@@ -65,7 +65,7 @@ jobs:
         uses: Homebrew/actions/setup-homebrew@master
 
       - name: Checkout code-server
-        uses: actions/checkout@v4
+        uses: actions/checkout@v5
 
       - name: Configure git
         run: |
@@ -94,13 +94,13 @@ jobs:
     steps:
       # We need to checkout code-server so we can get the version
       - name: Checkout code-server
-        uses: actions/checkout@v4
+        uses: actions/checkout@v5
         with:
           fetch-depth: 0
           path: "./code-server"
 
       - name: Checkout code-server-aur repo
-        uses: actions/checkout@v4
+        uses: actions/checkout@v5
         with:
           repository: "cdrci/code-server-aur"
           token: ${{ secrets.HOMEBREW_GITHUB_API_TOKEN }}
@@ -148,7 +148,7 @@ jobs:
     runs-on: ubuntu-latest
     steps:
       - name: Checkout code-server
-        uses: actions/checkout@v4
+        uses: actions/checkout@v5
 
       - name: Set up QEMU
         uses: docker/setup-qemu-action@v3
diff --git a/.github/workflows/release.yaml b/.github/workflows/release.yaml
index a16fc6b90ac7..2536983d2b45 100644
--- a/.github/workflows/release.yaml
+++ b/.github/workflows/release.yaml
@@ -60,7 +60,7 @@ jobs:
 
     steps:
       - name: Checkout repo
-        uses: actions/checkout@v4
+        uses: actions/checkout@v5
 
       - name: Install Node.js
         uses: actions/setup-node@v4
@@ -94,7 +94,7 @@ jobs:
           echo "$HOME/.local/bin" >> $GITHUB_PATH
 
       - name: Download npm package
-        uses: actions/download-artifact@v4
+        uses: actions/download-artifact@v5
         with:
           name: npm-release-package
 
@@ -134,7 +134,7 @@ jobs:
 
     steps:
       - name: Checkout repo
-        uses: actions/checkout@v4
+        uses: actions/checkout@v5
 
       - name: Install Node.js
         uses: actions/setup-node@v4
@@ -160,7 +160,7 @@ jobs:
       - run: brew install python-setuptools
 
       - name: Download npm package
-        uses: actions/download-artifact@v4
+        uses: actions/download-artifact@v5
         with:
           name: npm-release-package
 
@@ -195,7 +195,7 @@ jobs:
 
     steps:
       - name: Checkout repo
-        uses: actions/checkout@v4
+        uses: actions/checkout@v5
 
       - name: Install Node.js
         uses: actions/setup-node@v4
@@ -221,7 +221,7 @@ jobs:
       - run: brew install python-setuptools
 
       - name: Download npm package
-        uses: actions/download-artifact@v4
+        uses: actions/download-artifact@v5
         with:
           name: npm-release-package
 
@@ -253,7 +253,7 @@ jobs:
     needs: npm-version
     steps:
       - name: Download npm package
-        uses: actions/download-artifact@v4
+        uses: actions/download-artifact@v5
         with:
           name: npm-release-package
 
diff --git a/.github/workflows/scripts.yaml b/.github/workflows/scripts.yaml
index d3ca65cbc548..a39d90ad4c96 100644
--- a/.github/workflows/scripts.yaml
+++ b/.github/workflows/scripts.yaml
@@ -41,7 +41,7 @@ jobs:
     container: "alpine:3.17"
     steps:
       - name: Checkout repo
-        uses: actions/checkout@v4
+        uses: actions/checkout@v5
 
       - name: Install test utilities
         run: apk add bats checkbashisms
@@ -58,7 +58,7 @@ jobs:
     timeout-minutes: 5
     steps:
       - name: Checkout repo
-        uses: actions/checkout@v4
+        uses: actions/checkout@v5
 
       - name: Install lint utilities
         run: sudo apt install shellcheck
diff --git a/.github/workflows/security.yaml b/.github/workflows/security.yaml
index a14094d92e82..d8afcfce34d7 100644
--- a/.github/workflows/security.yaml
+++ b/.github/workflows/security.yaml
@@ -25,7 +25,7 @@ jobs:
     timeout-minutes: 15
     steps:
       - name: Checkout repo
-        uses: actions/checkout@v4
+        uses: actions/checkout@v5
         with:
           fetch-depth: 0
 
@@ -46,12 +46,12 @@ jobs:
     runs-on: ubuntu-22.04
     steps:
       - name: Checkout repo
-        uses: actions/checkout@v4
+        uses: actions/checkout@v5
         with:
           fetch-depth: 0
 
       - name: Run Trivy vulnerability scanner in repo mode
-        uses: aquasecurity/trivy-action@dc5a429b52fcf669ce959baa2c2dd26090d2a6c4
+        uses: aquasecurity/trivy-action@b6643a29fecd7f34b3597bc6acb0a98b03d33ff8
         with:
           scan-type: "fs"
           scan-ref: "."
@@ -76,7 +76,7 @@ jobs:
 
     steps:
       - name: Checkout repository
-        uses: actions/checkout@v4
+        uses: actions/checkout@v5
 
       # Initializes the CodeQL tools for scanning.
       - name: Initialize CodeQL
diff --git a/.github/workflows/trivy-docker.yaml b/.github/workflows/trivy-docker.yaml
index 06ca72ae6429..97769603da9e 100644
--- a/.github/workflows/trivy-docker.yaml
+++ b/.github/workflows/trivy-docker.yaml
@@ -48,10 +48,10 @@ jobs:
 
     steps:
       - name: Checkout code
-        uses: actions/checkout@v4
+        uses: actions/checkout@v5
 
       - name: Run Trivy vulnerability scanner in image mode
-        uses: aquasecurity/trivy-action@dc5a429b52fcf669ce959baa2c2dd26090d2a6c4
+        uses: aquasecurity/trivy-action@b6643a29fecd7f34b3597bc6acb0a98b03d33ff8
         with:
           image-ref: "docker.io/codercom/code-server:latest"
           ignore-unfixed: true
diff --git a/.node-version b/.node-version
index 91d5f6ff8e3f..e2228113dd09 100644
--- a/.node-version
+++ b/.node-version
@@ -1 +1 @@
-22.18.0
+22.19.0
diff --git a/CHANGELOG.md b/CHANGELOG.md
index 4c177c17efda..3ba0b42cb005 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -22,6 +22,22 @@ Code v99.99.999
 
 ## Unreleased
 
+## [4.104.2](https://github.com/coder/code-server/releases/tag/v4.104.2) - 2025-09-26
+
+Code v1.104.2
+
+### Changed
+
+- Update to Code 1.104.2.
+
+## [4.104.1](https://github.com/coder/code-server/releases/tag/v4.104.1) - 2025-09-19
+
+Code v1.104.1
+
+### Changed
+
+- Update to Code 1.104.1.
+
 ## [4.104.0](https://github.com/coder/code-server/releases/tag/v4.104.0) - 2025-09-15
 
 Code v1.104.0
diff --git a/ci/helm-chart/Chart.yaml b/ci/helm-chart/Chart.yaml
index 7d62f273000c..00e7221ee109 100644
--- a/ci/helm-chart/Chart.yaml
+++ b/ci/helm-chart/Chart.yaml
@@ -15,9 +15,9 @@ type: application
 # This is the chart version. This version number should be incremented each time you make changes
 # to the chart and its templates, including the app version.
 # Versions are expected to follow Semantic Versioning (https://semver.org/)
-version: 3.31.0
+version: 3.31.2
 
 # This is the version number of the application being deployed. This version number should be
 # incremented each time you make changes to the application. Versions are not expected to
 # follow Semantic Versioning. They should reflect the version the application is using.
-appVersion: 4.104.0
+appVersion: 4.104.2
diff --git a/ci/helm-chart/values.yaml b/ci/helm-chart/values.yaml
index 7a9a2676144a..a414de0da0ec 100644
--- a/ci/helm-chart/values.yaml
+++ b/ci/helm-chart/values.yaml
@@ -6,7 +6,7 @@ replicaCount: 1
 
 image:
   repository: codercom/code-server
-  tag: '4.104.0'
+  tag: '4.104.2'
   pullPolicy: Always
 
 # Specifies one or more secrets to be used when pulling images from a
diff --git a/docs/FAQ.md b/docs/FAQ.md
index 2e01306cb2f2..a695cc64ac6a 100644
--- a/docs/FAQ.md
+++ b/docs/FAQ.md
@@ -322,12 +322,8 @@ As long as there is an active browser connection, code-server touches
 `~/.local/share/code-server/heartbeat` once a minute.
 
 If you want to shutdown code-server if there hasn't been an active connection
-after a predetermined amount of time, you can do so by checking continuously for
-the last modified time on the heartbeat file. If it is older than X minutes (or
-whatever amount of time you'd like), you can kill code-server.
-
-Eventually, [#1636](https://github.com/coder/code-server/issues/1636) will make
-this process better.
+after a predetermined amount of time, you can use the --idle-timeout-seconds flag
+or set an `CODE_SERVER_IDLE_TIMEOUT_SECONDS` environment variable.
 
 ## How do I change the password?
 
diff --git a/docs/android.md b/docs/android.md
index 2659c44000b8..0b1dc24abf6e 100644
--- a/docs/android.md
+++ b/docs/android.md
@@ -14,8 +14,8 @@ curl -o- https://raw.githubusercontent.com/nvm-sh/nvm/v0.39.0/install.sh | bash
 7. Install and use Node.js 22:
 
 ```shell
-nvm install 18
-nvm use 18
+nvm install 22
+nvm use 22
 ```
 
 8. Install code-server globally on device with: `npm install --global code-server`
diff --git a/lib/vscode b/lib/vscode
index 0f0d87fa9e96..7d842fb85a02 160000
--- a/lib/vscode
+++ b/lib/vscode
@@ -1 +1 @@
-Subproject commit 0f0d87fa9e96c856c5212fc86db137ac0d783365
+Subproject commit 7d842fb85a0275a4a8e4d7e040d2625abbf7f084
diff --git a/package-lock.json b/package-lock.json
index 2c98099e0bb5..8bd50af3431d 100644
--- a/package-lock.json
+++ b/package-lock.json
@@ -128,9 +128,9 @@
       }
     },
     "node_modules/@eslint-community/eslint-utils": {
-      "version": "4.7.0",
-      "resolved": "https://registry.npmjs.org/@eslint-community/eslint-utils/-/eslint-utils-4.7.0.tgz",
-      "integrity": "sha512-dyybb3AcajC7uha6CvhdVRJqaKyn7w2YKqKyAN37NKYgZT36w+iRb0Dymmc5qEJ549c/S31cMMSFd75bteCpCw==",
+      "version": "4.9.0",
+      "resolved": "https://registry.npmjs.org/@eslint-community/eslint-utils/-/eslint-utils-4.9.0.tgz",
+      "integrity": "sha512-ayVFHdtZ+hsq1t2Dy24wCmGXGe4q9Gu3smhLYALJrr473ZH27MsnSL+LKUlimp4BWJqMDMLmPpx/Q9R3OAlL4g==",
       "dev": true,
       "license": "MIT",
       "dependencies": {
@@ -190,9 +190,9 @@
       }
     },
     "node_modules/@eslint/config-helpers": {
-      "version": "0.3.0",
-      "resolved": "https://registry.npmjs.org/@eslint/config-helpers/-/config-helpers-0.3.0.tgz",
-      "integrity": "sha512-ViuymvFmcJi04qdZeDc2whTHryouGcDlaxPqarTD0ZE10ISpxGUVZGZDx4w01upyIynL3iu6IXH2bS1NhclQMw==",
+      "version": "0.3.1",
+      "resolved": "https://registry.npmjs.org/@eslint/config-helpers/-/config-helpers-0.3.1.tgz",
+      "integrity": "sha512-xR93k9WhrDYpXHORXpxVL5oHj3Era7wo6k/Wd8/IsQNnZUTzkGS29lyn3nAT05v6ltUuTFVCCYDEGfy2Or/sPA==",
       "dev": true,
       "license": "Apache-2.0",
       "engines": {
@@ -200,9 +200,9 @@
       }
     },
     "node_modules/@eslint/core": {
-      "version": "0.15.1",
-      "resolved": "https://registry.npmjs.org/@eslint/core/-/core-0.15.1.tgz",
-      "integrity": "sha512-bkOp+iumZCCbt1K1CmWf0R9pM5yKpDv+ZXtvSyQpudrI9kuFLp+bM2WOPXImuD/ceQuaa8f5pj93Y7zyECIGNA==",
+      "version": "0.15.2",
+      "resolved": "https://registry.npmjs.org/@eslint/core/-/core-0.15.2.tgz",
+      "integrity": "sha512-78Md3/Rrxh83gCxoUc0EiciuOHsIITzLy53m3d9UyiW8y9Dj2D29FeETqyKA+BRK76tnTp6RXWb3pCay8Oyomg==",
       "dev": true,
       "license": "Apache-2.0",
       "dependencies": {
@@ -250,9 +250,9 @@
       }
     },
     "node_modules/@eslint/js": {
-      "version": "9.32.0",
-      "resolved": "https://registry.npmjs.org/@eslint/js/-/js-9.32.0.tgz",
-      "integrity": "sha512-BBpRFZK3eX6uMLKz8WxFOBIFFcGFJ/g8XuwjTHCqHROSIsopI+ddn/d5Cfh36+7+e5edVS8dbSHnBNhrLEX0zg==",
+      "version": "9.36.0",
+      "resolved": "https://registry.npmjs.org/@eslint/js/-/js-9.36.0.tgz",
+      "integrity": "sha512-uhCbYtYynH30iZErszX78U+nR3pJU3RHGQ57NXy5QupD4SBVwDeU8TNBy+MjMngc1UyIW9noKqsRqfjQTBU2dw==",
       "dev": true,
       "license": "MIT",
       "engines": {
@@ -273,13 +273,13 @@
       }
     },
     "node_modules/@eslint/plugin-kit": {
-      "version": "0.3.4",
-      "resolved": "https://registry.npmjs.org/@eslint/plugin-kit/-/plugin-kit-0.3.4.tgz",
-      "integrity": "sha512-Ul5l+lHEcw3L5+k8POx6r74mxEYKG5kOb6Xpy2gCRW6zweT6TEhAf8vhxGgjhqrd/VO/Dirhsb+1hNpD1ue9hw==",
+      "version": "0.3.5",
+      "resolved": "https://registry.npmjs.org/@eslint/plugin-kit/-/plugin-kit-0.3.5.tgz",
+      "integrity": "sha512-Z5kJ+wU3oA7MMIqVR9tyZRtjYPr4OC004Q4Rw7pgOKUOKkJfZ3O24nz3WYfGRpMDNmcOi3TwQOmgm7B7Tpii0w==",
       "dev": true,
       "license": "Apache-2.0",
       "dependencies": {
-        "@eslint/core": "^0.15.1",
+        "@eslint/core": "^0.15.2",
         "levn": "^0.4.1"
       },
       "engines": {
@@ -610,15 +610,14 @@
       "license": "MIT"
     },
     "node_modules/@types/express": {
-      "version": "5.0.0",
-      "resolved": "https://registry.npmjs.org/@types/express/-/express-5.0.0.tgz",
-      "integrity": "sha512-DvZriSMehGHL1ZNLzi6MidnsDhUZM/x2pRdDIKdwbUNqqwHxMlRdkxtn6/EPKyqKpHqTl/4nRZsRNLpZxZRpPQ==",
+      "version": "5.0.3",
+      "resolved": "https://registry.npmjs.org/@types/express/-/express-5.0.3.tgz",
+      "integrity": "sha512-wGA0NX93b19/dZC1J18tKWVIYWyyF2ZjT9vin/NRu0qzzvfVzWjs04iq2rQ3H65vCTQYlRqs3YHfY7zjdV+9Kw==",
       "dev": true,
       "license": "MIT",
       "dependencies": {
         "@types/body-parser": "*",
         "@types/express-serve-static-core": "^5.0.0",
-        "@types/qs": "*",
         "@types/serve-static": "*"
       }
     },
@@ -1640,18 +1639,18 @@
       }
     },
     "node_modules/body-parser": {
-      "version": "2.1.0",
-      "resolved": "https://registry.npmjs.org/body-parser/-/body-parser-2.1.0.tgz",
-      "integrity": "sha512-/hPxh61E+ll0Ujp24Ilm64cykicul1ypfwjVttduAiEdtnJFvLePSrIPk+HMImtNv5270wOGCb1Tns2rybMkoQ==",
+      "version": "2.2.0",
+      "resolved": "https://registry.npmjs.org/body-parser/-/body-parser-2.2.0.tgz",
+      "integrity": "sha512-02qvAaxv8tp7fBa/mw1ga98OGm+eCbqzJOKoRt70sLmfEEi+jyBYVTDGfCL/k06/4EMk/z01gCe7HoCH/f2LTg==",
       "license": "MIT",
       "dependencies": {
         "bytes": "^3.1.2",
         "content-type": "^1.0.5",
         "debug": "^4.4.0",
         "http-errors": "^2.0.0",
-        "iconv-lite": "^0.5.2",
+        "iconv-lite": "^0.6.3",
         "on-finished": "^2.4.1",
-        "qs": "6.14.0",
+        "qs": "^6.14.0",
         "raw-body": "^3.0.0",
         "type-is": "^2.0.0"
       },
@@ -2150,16 +2149,6 @@
         "node": ">= 0.8"
       }
     },
-    "node_modules/destroy": {
-      "version": "1.2.0",
-      "resolved": "https://registry.npmjs.org/destroy/-/destroy-1.2.0.tgz",
-      "integrity": "sha512-2sJGJTaXIIaR1w4iJSNoN0hnMY7Gpc/n8D4qSCJw8QqFWXf7cuAgnEHxBpweaVcPevC2l3KpjYCx3NypQQgaJg==",
-      "license": "MIT",
-      "engines": {
-        "node": ">= 0.8",
-        "npm": "1.2.8000 || >= 1.4.16"
-      }
-    },
     "node_modules/detect-libc": {
       "version": "2.0.3",
       "resolved": "https://registry.npmjs.org/detect-libc/-/detect-libc-2.0.3.tgz",
@@ -2490,20 +2479,20 @@
       }
     },
     "node_modules/eslint": {
-      "version": "9.32.0",
-      "resolved": "https://registry.npmjs.org/eslint/-/eslint-9.32.0.tgz",
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     "node_modules/v8-compile-cache-lib": {
       "version": "3.0.1",
       "resolved": "https://registry.npmjs.org/v8-compile-cache-lib/-/v8-compile-cache-lib-3.0.1.tgz",
diff --git a/patches/base-path.diff b/patches/base-path.diff
index 31db2231a939..5c6e5b8b1e31 100644
--- a/patches/base-path.diff
+++ b/patches/base-path.diff
@@ -105,8 +105,8 @@ Index: code-server/lib/vscode/src/vs/platform/remote/browser/browserSocketFactor
  			const webSocketSchema = (/^https:/.test(mainWindow.location.href) ? 'wss' : 'ws');
 +			path = (mainWindow.location.pathname + "/" + path).replace(/\/\/+/g, "/")
  			const socket = this._webSocketFactory.create(`${webSocketSchema}://${(/:/.test(host) && !/\[/.test(host)) ? `[${host}]` : host}:${port}${path}?${query}&skipWebSocketFrames=false`, debugLabel);
- 			const errorListener = socket.onError(reject);
- 			socket.onOpen(() => {
+ 			const disposables = new DisposableStore();
+ 			disposables.add(socket.onError(reject));
 Index: code-server/lib/vscode/src/vs/server/node/webClientServer.ts
 ===================================================================
 --- code-server.orig/lib/vscode/src/vs/server/node/webClientServer.ts
diff --git a/patches/cli-window-open.diff b/patches/cli-window-open.diff
index 8da64b2a5d70..3bc21fa3b4bc 100644
--- a/patches/cli-window-open.diff
+++ b/patches/cli-window-open.diff
@@ -17,7 +17,7 @@ Index: code-server/lib/vscode/src/vs/workbench/contrib/terminal/browser/remoteTe
 ===================================================================
 --- code-server.orig/lib/vscode/src/vs/workbench/contrib/terminal/browser/remoteTerminalBackend.ts
 +++ code-server/lib/vscode/src/vs/workbench/contrib/terminal/browser/remoteTerminalBackend.ts
-@@ -106,10 +106,14 @@ class RemoteTerminalBackend extends Base
+@@ -107,10 +107,14 @@ class RemoteTerminalBackend extends Base
  			}
  			const reqId = e.reqId;
  			const commandId = e.commandId;
diff --git a/patches/clipboard.diff b/patches/clipboard.diff
index 02c7d54dfd93..ecf6a09e30f3 100644
--- a/patches/clipboard.diff
+++ b/patches/clipboard.diff
@@ -65,7 +65,7 @@ Index: code-server/lib/vscode/src/vs/workbench/contrib/terminal/browser/remoteTe
 ===================================================================
 --- code-server.orig/lib/vscode/src/vs/workbench/contrib/terminal/browser/remoteTerminalBackend.ts
 +++ code-server/lib/vscode/src/vs/workbench/contrib/terminal/browser/remoteTerminalBackend.ts
-@@ -97,7 +97,7 @@ class RemoteTerminalBackend extends Base
+@@ -98,7 +98,7 @@ class RemoteTerminalBackend extends Base
  			}
  		});
  
@@ -78,7 +78,7 @@ Index: code-server/lib/vscode/src/vs/platform/environment/common/argv.ts
 ===================================================================
 --- code-server.orig/lib/vscode/src/vs/platform/environment/common/argv.ts
 +++ code-server/lib/vscode/src/vs/platform/environment/common/argv.ts
-@@ -135,6 +135,7 @@ export interface NativeParsedArgs {
+@@ -136,6 +136,7 @@ export interface NativeParsedArgs {
  	'disable-chromium-sandbox'?: boolean;
  	sandbox?: boolean;
  	'enable-coi'?: boolean;
@@ -90,7 +90,7 @@ Index: code-server/lib/vscode/src/vs/platform/environment/node/argv.ts
 ===================================================================
 --- code-server.orig/lib/vscode/src/vs/platform/environment/node/argv.ts
 +++ code-server/lib/vscode/src/vs/platform/environment/node/argv.ts
-@@ -104,6 +104,7 @@ export const OPTIONS: OptionDescriptions
+@@ -105,6 +105,7 @@ export const OPTIONS: OptionDescriptions
  	'user-data-dir': { type: 'string', cat: 'o', args: 'dir', description: localize('userDataDir', "Specifies the directory that user data is kept in. Can be used to open multiple distinct instances of Code.") },
  	'profile': { type: 'string', 'cat': 'o', args: 'profileName', description: localize('profileName', "Opens the provided folder or workspace with the given profile and associates the profile with the workspace. If the profile does not exist, a new empty one is created.") },
  	'help': { type: 'boolean', cat: 'o', alias: 'h', description: localize('help', "Print usage.") },
diff --git a/patches/external-file-actions.diff b/patches/external-file-actions.diff
index 8a6830d00eca..ef92e1c46361 100644
--- a/patches/external-file-actions.diff
+++ b/patches/external-file-actions.diff
@@ -125,13 +125,12 @@ Index: code-server/lib/vscode/src/vs/workbench/browser/contextkeys.ts
 ===================================================================
 --- code-server.orig/lib/vscode/src/vs/workbench/browser/contextkeys.ts
 +++ code-server/lib/vscode/src/vs/workbench/browser/contextkeys.ts
-@@ -7,11 +7,11 @@ import { Event } from '../../base/common
- import { Disposable, DisposableStore, MutableDisposable } from '../../base/common/lifecycle.js';
+@@ -6,10 +6,10 @@
+ import { Disposable } from '../../base/common/lifecycle.js';
  import { IContextKeyService, IContextKey, setConstant as setConstantContextKey } from '../../platform/contextkey/common/contextkey.js';
- import { InputFocusedContext, IsMacContext, IsLinuxContext, IsWindowsContext, IsWebContext, IsMacNativeContext, IsDevelopmentContext, IsIOSContext, ProductQualityContext, IsMobileContext, IsSimulationContext } from '../../platform/contextkey/common/contextkeys.js';
+ import { IsMacContext, IsLinuxContext, IsWindowsContext, IsWebContext, IsMacNativeContext, IsDevelopmentContext, IsIOSContext, ProductQualityContext, IsMobileContext } from '../../platform/contextkey/common/contextkeys.js';
 -import { SplitEditorsVertically, InEditorZenModeContext, AuxiliaryBarVisibleContext, SideBarVisibleContext, PanelAlignmentContext, PanelMaximizedContext, PanelVisibleContext, EmbedderIdentifierContext, EditorTabsVisibleContext, IsMainEditorCenteredLayoutContext, MainEditorAreaVisibleContext, DirtyWorkingCopiesContext, EmptyWorkspaceSupportContext, EnterMultiRootWorkspaceSupportContext, HasWebFileSystemAccess, IsMainWindowFullscreenContext, OpenFolderWorkspaceSupportContext, RemoteNameContext, VirtualWorkspaceContext, WorkbenchStateContext, WorkspaceFolderCountContext, PanelPositionContext, TemporaryWorkspaceContext, TitleBarVisibleContext, TitleBarStyleContext, IsAuxiliaryWindowFocusedContext, ActiveEditorGroupEmptyContext, ActiveEditorGroupIndexContext, ActiveEditorGroupLastContext, ActiveEditorGroupLockedContext, MultipleEditorGroupsContext, EditorsVisibleContext, AuxiliaryBarMaximizedContext, InAutomationContext } from '../common/contextkeys.js';
 +import { SplitEditorsVertically, InEditorZenModeContext, AuxiliaryBarVisibleContext, SideBarVisibleContext, PanelAlignmentContext, PanelMaximizedContext, PanelVisibleContext, EmbedderIdentifierContext, EditorTabsVisibleContext, IsMainEditorCenteredLayoutContext, MainEditorAreaVisibleContext, DirtyWorkingCopiesContext, EmptyWorkspaceSupportContext, EnterMultiRootWorkspaceSupportContext, HasWebFileSystemAccess, IsMainWindowFullscreenContext, OpenFolderWorkspaceSupportContext, RemoteNameContext, VirtualWorkspaceContext, WorkbenchStateContext, WorkspaceFolderCountContext, PanelPositionContext, TemporaryWorkspaceContext, TitleBarVisibleContext, TitleBarStyleContext, IsAuxiliaryWindowFocusedContext, ActiveEditorGroupEmptyContext, ActiveEditorGroupIndexContext, ActiveEditorGroupLastContext, ActiveEditorGroupLockedContext, MultipleEditorGroupsContext, EditorsVisibleContext, AuxiliaryBarMaximizedContext, InAutomationContext, IsEnabledFileDownloads, IsEnabledFileUploads } from '../common/contextkeys.js';
- import { trackFocus, addDisposableListener, EventType, onDidRegisterWindow, getActiveWindow, isEditableElement } from '../../base/browser/dom.js';
  import { preferredSideBySideGroupDirection, GroupDirection, IEditorGroupsService } from '../services/editor/common/editorGroupsService.js';
  import { IConfigurationService } from '../../platform/configuration/common/configuration.js';
 -import { IWorkbenchEnvironmentService } from '../services/environment/common/environmentService.js';
@@ -139,7 +138,7 @@ Index: code-server/lib/vscode/src/vs/workbench/browser/contextkeys.ts
  import { WorkbenchState, IWorkspaceContextService, isTemporaryWorkspace } from '../../platform/workspace/common/workspace.js';
  import { IWorkbenchLayoutService, Parts, positionToString } from '../services/layout/browser/layoutService.js';
  import { getRemoteName } from '../../platform/remote/common/remoteHosts.js';
-@@ -72,7 +72,7 @@ export class WorkbenchContextKeysHandler
+@@ -69,7 +69,7 @@ export class WorkbenchContextKeysHandler
  		@IContextKeyService private readonly contextKeyService: IContextKeyService,
  		@IWorkspaceContextService private readonly contextService: IWorkspaceContextService,
  		@IConfigurationService private readonly configurationService: IConfigurationService,
@@ -148,7 +147,7 @@ Index: code-server/lib/vscode/src/vs/workbench/browser/contextkeys.ts
  		@IProductService private readonly productService: IProductService,
  		@IEditorGroupsService private readonly editorGroupService: IEditorGroupsService,
  		@IEditorService private readonly editorService: IEditorService,
-@@ -208,6 +208,10 @@ export class WorkbenchContextKeysHandler
+@@ -199,6 +199,10 @@ export class WorkbenchContextKeysHandler
  		this.auxiliaryBarMaximizedContext = AuxiliaryBarMaximizedContext.bindTo(this.contextKeyService);
  		this.auxiliaryBarMaximizedContext.set(this.layoutService.isAuxiliaryBarMaximized());
  
diff --git a/patches/getting-started.diff b/patches/getting-started.diff
index 14ab7f4d57e1..c5fd5d6ccbac 100644
--- a/patches/getting-started.diff
+++ b/patches/getting-started.diff
@@ -213,16 +213,16 @@ Index: code-server/lib/vscode/src/vs/workbench/browser/contextkeys.ts
 ===================================================================
 --- code-server.orig/lib/vscode/src/vs/workbench/browser/contextkeys.ts
 +++ code-server/lib/vscode/src/vs/workbench/browser/contextkeys.ts
-@@ -7,7 +7,7 @@ import { Event } from '../../base/common
- import { Disposable, DisposableStore, MutableDisposable } from '../../base/common/lifecycle.js';
+@@ -6,7 +6,7 @@
+ import { Disposable } from '../../base/common/lifecycle.js';
  import { IContextKeyService, IContextKey, setConstant as setConstantContextKey } from '../../platform/contextkey/common/contextkey.js';
- import { InputFocusedContext, IsMacContext, IsLinuxContext, IsWindowsContext, IsWebContext, IsMacNativeContext, IsDevelopmentContext, IsIOSContext, ProductQualityContext, IsMobileContext, IsSimulationContext } from '../../platform/contextkey/common/contextkeys.js';
+ import { IsMacContext, IsLinuxContext, IsWindowsContext, IsWebContext, IsMacNativeContext, IsDevelopmentContext, IsIOSContext, ProductQualityContext, IsMobileContext } from '../../platform/contextkey/common/contextkeys.js';
 -import { SplitEditorsVertically, InEditorZenModeContext, AuxiliaryBarVisibleContext, SideBarVisibleContext, PanelAlignmentContext, PanelMaximizedContext, PanelVisibleContext, EmbedderIdentifierContext, EditorTabsVisibleContext, IsMainEditorCenteredLayoutContext, MainEditorAreaVisibleContext, DirtyWorkingCopiesContext, EmptyWorkspaceSupportContext, EnterMultiRootWorkspaceSupportContext, HasWebFileSystemAccess, IsMainWindowFullscreenContext, OpenFolderWorkspaceSupportContext, RemoteNameContext, VirtualWorkspaceContext, WorkbenchStateContext, WorkspaceFolderCountContext, PanelPositionContext, TemporaryWorkspaceContext, TitleBarVisibleContext, TitleBarStyleContext, IsAuxiliaryWindowFocusedContext, ActiveEditorGroupEmptyContext, ActiveEditorGroupIndexContext, ActiveEditorGroupLastContext, ActiveEditorGroupLockedContext, MultipleEditorGroupsContext, EditorsVisibleContext, AuxiliaryBarMaximizedContext, InAutomationContext, IsEnabledFileDownloads, IsEnabledFileUploads } from '../common/contextkeys.js';
 +import { SplitEditorsVertically, InEditorZenModeContext, AuxiliaryBarVisibleContext, SideBarVisibleContext, PanelAlignmentContext, PanelMaximizedContext, PanelVisibleContext, EmbedderIdentifierContext, EditorTabsVisibleContext, IsMainEditorCenteredLayoutContext, MainEditorAreaVisibleContext, DirtyWorkingCopiesContext, EmptyWorkspaceSupportContext, EnterMultiRootWorkspaceSupportContext, HasWebFileSystemAccess, IsMainWindowFullscreenContext, OpenFolderWorkspaceSupportContext, RemoteNameContext, VirtualWorkspaceContext, WorkbenchStateContext, WorkspaceFolderCountContext, PanelPositionContext, TemporaryWorkspaceContext, TitleBarVisibleContext, TitleBarStyleContext, IsAuxiliaryWindowFocusedContext, ActiveEditorGroupEmptyContext, ActiveEditorGroupIndexContext, ActiveEditorGroupLastContext, ActiveEditorGroupLockedContext, MultipleEditorGroupsContext, EditorsVisibleContext, AuxiliaryBarMaximizedContext, InAutomationContext, IsEnabledFileDownloads, IsEnabledFileUploads, IsEnabledCoderGettingStarted, } from '../common/contextkeys.js';
- import { trackFocus, addDisposableListener, EventType, onDidRegisterWindow, getActiveWindow, isEditableElement } from '../../base/browser/dom.js';
  import { preferredSideBySideGroupDirection, GroupDirection, IEditorGroupsService } from '../services/editor/common/editorGroupsService.js';
  import { IConfigurationService } from '../../platform/configuration/common/configuration.js';
-@@ -211,6 +211,7 @@ export class WorkbenchContextKeysHandler
+ import { IBrowserWorkbenchEnvironmentService } from '../services/environment/browser/environmentService.js';
+@@ -202,6 +202,7 @@ export class WorkbenchContextKeysHandler
  		// code-server
  		IsEnabledFileDownloads.bindTo(this.contextKeyService).set(this.environmentService.isEnabledFileDownloads ?? true)
  		IsEnabledFileUploads.bindTo(this.contextKeyService).set(this.environmentService.isEnabledFileUploads ?? true)
diff --git a/src/node/cli.ts b/src/node/cli.ts
index 70ede42a0591..0fce9cfbf25f 100644
--- a/src/node/cli.ts
+++ b/src/node/cli.ts
@@ -94,6 +94,7 @@ export interface UserProvidedArgs extends UserProvidedCodeArgs {
   "welcome-text"?: string
   "abs-proxy-base-path"?: string
   i18n?: string
+  "idle-timeout-seconds"?: number
   /* Positional arguments. */
   _?: string[]
 }
@@ -303,6 +304,10 @@ export const options: Options<Required<UserProvidedArgs>> = {
     path: true,
     description: "Path to JSON file with custom translations. Merges with default strings and supports all i18n keys.",
   },
+  "idle-timeout-seconds": {
+    type: "number",
+    description: "Timeout in seconds to wait before shutting down when idle.",
+  },
 }
 
 export const optionDescriptions = (opts: Partial<Options<Required<UserProvidedArgs>>> = options): string[] => {
@@ -396,6 +401,10 @@ export const parse = (
         throw new Error("--github-auth can only be set in the config file or passed in via $GITHUB_TOKEN")
       }
 
+      if (key === "idle-timeout-seconds" && Number(value) <= 60) {
+        throw new Error("--idle-timeout-seconds must be greater than 60 seconds.")
+      }
+
       const option = options[key]
       if (option.type === "boolean") {
         ;(args[key] as boolean) = true
@@ -611,6 +620,16 @@ export async function setDefaults(cliArgs: UserProvidedArgs, configArgs?: Config
     args["github-auth"] = process.env.GITHUB_TOKEN
   }
 
+  if (process.env.CODE_SERVER_IDLE_TIMEOUT_SECONDS) {
+    if (isNaN(Number(process.env.CODE_SERVER_IDLE_TIMEOUT_SECONDS))) {
+      logger.info("CODE_SERVER_IDLE_TIMEOUT_SECONDS must be a number")
+    }
+    if (Number(process.env.CODE_SERVER_IDLE_TIMEOUT_SECONDS) <= 60) {
+      throw new Error("--idle-timeout-seconds must be greater than 60 seconds.")
+    }
+    args["idle-timeout-seconds"] = Number(process.env.CODE_SERVER_IDLE_TIMEOUT_SECONDS)
+  }
+
   // Ensure they're not readable by child processes.
   delete process.env.PASSWORD
   delete process.env.HASHED_PASSWORD
diff --git a/src/node/heart.ts b/src/node/heart.ts
index aac917257f23..b78f4edb80d2 100644
--- a/src/node/heart.ts
+++ b/src/node/heart.ts
@@ -1,5 +1,6 @@
 import { logger } from "@coder/logger"
 import { promises as fs } from "fs"
+import { Emitter } from "../common/emitter"
 
 /**
  * Provides a heartbeat using a local file to indicate activity.
@@ -8,6 +9,9 @@ export class Heart {
   private heartbeatTimer?: NodeJS.Timeout
   private heartbeatInterval = 60000
   public lastHeartbeat = 0
+  private readonly _onChange = new Emitter<"alive" | "expired" | "unknown">()
+  readonly onChange = this._onChange.event
+  private state: "alive" | "expired" | "unknown" = "expired"
 
   public constructor(
     private readonly heartbeatPath: string,
@@ -17,6 +21,13 @@ export class Heart {
     this.alive = this.alive.bind(this)
   }
 
+  private setState(state: typeof this.state) {
+    if (this.state !== state) {
+      this.state = state
+      this._onChange.emit(this.state)
+    }
+  }
+
   public alive(): boolean {
     const now = Date.now()
     return now - this.lastHeartbeat < this.heartbeatInterval
@@ -28,6 +39,7 @@ export class Heart {
    */
   public async beat(): Promise<void> {
     if (this.alive()) {
+      this.setState("alive")
       return
     }
 
@@ -36,7 +48,22 @@ export class Heart {
     if (typeof this.heartbeatTimer !== "undefined") {
       clearTimeout(this.heartbeatTimer)
     }
-    this.heartbeatTimer = setTimeout(() => heartbeatTimer(this.isActive, this.beat), this.heartbeatInterval)
+
+    this.heartbeatTimer = setTimeout(async () => {
+      try {
+        if (await this.isActive()) {
+          this.beat()
+        } else {
+          this.setState("expired")
+        }
+      } catch (error: unknown) {
+        logger.warn((error as Error).message)
+        this.setState("unknown")
+      }
+    }, this.heartbeatInterval)
+
+    this.setState("alive")
+
     try {
       return await fs.writeFile(this.heartbeatPath, "")
     } catch (error: any) {
@@ -53,20 +80,3 @@ export class Heart {
     }
   }
 }
-
-/**
- * Helper function for the heartbeatTimer.
- *
- * If heartbeat is active, call beat. Otherwise do nothing.
- *
- * Extracted to make it easier to test.
- */
-export async function heartbeatTimer(isActive: Heart["isActive"], beat: Heart["beat"]) {
-  try {
-    if (await isActive()) {
-      beat()
-    }
-  } catch (error: unknown) {
-    logger.warn((error as Error).message)
-  }
-}
diff --git a/src/node/main.ts b/src/node/main.ts
index 6f8e28dbdea7..c2d3bd57852b 100644
--- a/src/node/main.ts
+++ b/src/node/main.ts
@@ -11,6 +11,7 @@ import { loadCustomStrings } from "./i18n"
 import { register } from "./routes"
 import { VSCodeModule } from "./routes/vscode"
 import { isDirectory, open } from "./util"
+import { wrapper } from "./wrapper"
 
 /**
  * Return true if the user passed an extension-related VS Code flag.
@@ -141,7 +142,7 @@ export const runCodeServer = async (
   const app = await createApp(args)
   const protocol = args.cert ? "https" : "http"
   const serverAddress = ensureAddress(app.server, protocol)
-  const disposeRoutes = await register(app, args)
+  const { disposeRoutes, heart } = await register(app, args)
 
   logger.info(`Using config file ${args.config}`)
   logger.info(`${protocol.toUpperCase()} server listening on ${serverAddress.toString()}`)
@@ -166,6 +167,27 @@ export const runCodeServer = async (
     logger.info("  - Not serving HTTPS")
   }
 
+  if (args["idle-timeout-seconds"]) {
+    logger.info(`  - Idle timeout set to ${args["idle-timeout-seconds"]} seconds`)
+
+    let idleShutdownTimer: NodeJS.Timeout | undefined
+    const startIdleShutdownTimer = () => {
+      idleShutdownTimer = setTimeout(() => {
+        logger.warn(`Idle timeout of ${args["idle-timeout-seconds"]} seconds exceeded`)
+        wrapper.exit(0)
+      }, args["idle-timeout-seconds"]! * 1000)
+    }
+
+    startIdleShutdownTimer()
+
+    heart.onChange((state) => {
+      clearTimeout(idleShutdownTimer)
+      if (state === "expired") {
+        startIdleShutdownTimer()
+      }
+    })
+  }
+
   if (args["disable-proxy"]) {
     logger.info("  - Proxy disabled")
   } else if (args["proxy-domain"].length > 0) {
diff --git a/src/node/routes/index.ts b/src/node/routes/index.ts
index 2841b5a01113..28bfc58d3ee7 100644
--- a/src/node/routes/index.ts
+++ b/src/node/routes/index.ts
@@ -28,7 +28,10 @@ import * as vscode from "./vscode"
 /**
  * Register all routes and middleware.
  */
-export const register = async (app: App, args: DefaultedArgs): Promise<Disposable["dispose"]> => {
+export const register = async (
+  app: App,
+  args: DefaultedArgs,
+): Promise<{ disposeRoutes: Disposable["dispose"]; heart: Heart }> => {
   const heart = new Heart(path.join(paths.data, "heartbeat"), async () => {
     return new Promise((resolve, reject) => {
       // getConnections appears to not call the callback when there are no more
@@ -173,8 +176,11 @@ export const register = async (app: App, args: DefaultedArgs): Promise<Disposabl
   app.router.use(errorHandler)
   app.wsRouter.use(wsErrorHandler)
 
-  return () => {
-    heart.dispose()
-    vscode.dispose()
+  return {
+    disposeRoutes: () => {
+      heart.dispose()
+      vscode.dispose()
+    },
+    heart,
   }
 }
diff --git a/test/package-lock.json b/test/package-lock.json
index f7ee4863c278..4e28618543cd 100644
--- a/test/package-lock.json
+++ b/test/package-lock.json
@@ -7,7 +7,7 @@
       "license": "MIT",
       "devDependencies": {
         "@jest-mock/express": "^1.4.5",
-        "@playwright/test": "^1.46.0",
+        "@playwright/test": "^1.56.1",
         "@types/jest": "^27.0.2",
         "@types/jsdom": "^16.2.13",
         "@types/node-fetch": "^2.5.8",
@@ -18,7 +18,7 @@
         "jest-fetch-mock": "^3.0.3",
         "jsdom": "^16.4.0",
         "node-fetch": "^2.6.7",
-        "playwright": "^1.46.0",
+        "playwright": "^1.56.1",
         "ts-jest": "^27.0.7",
         "wtfnode": "^0.9.1"
       }
@@ -1012,13 +1012,13 @@
       }
     },
     "node_modules/@playwright/test": {
-      "version": "1.47.2",
-      "resolved": "https://registry.npmjs.org/@playwright/test/-/test-1.47.2.tgz",
-      "integrity": "sha512-jTXRsoSPONAs8Za9QEQdyjFn+0ZQFjCiIztAIF6bi1HqhBzG9Ma7g1WotyiGqFSBRZjIEqMdT8RUlbk1QVhzCQ==",
+      "version": "1.56.1",
+      "resolved": "https://registry.npmjs.org/@playwright/test/-/test-1.56.1.tgz",
+      "integrity": "sha512-vSMYtL/zOcFpvJCW71Q/OEGQb7KYBPAdKh35WNSkaZA75JlAO8ED8UN6GUNTm3drWomcbcqRPFqQbLae8yBTdg==",
       "dev": true,
       "license": "Apache-2.0",
       "dependencies": {
-        "playwright": "1.47.2"
+        "playwright": "1.56.1"
       },
       "bin": {
         "playwright": "cli.js"
@@ -4305,13 +4305,13 @@
       }
     },
     "node_modules/playwright": {
-      "version": "1.47.2",
-      "resolved": "https://registry.npmjs.org/playwright/-/playwright-1.47.2.tgz",
-      "integrity": "sha512-nx1cLMmQWqmA3UsnjaaokyoUpdVaaDhJhMoxX2qj3McpjnsqFHs516QAKYhqHAgOP+oCFTEOCOAaD1RgD/RQfA==",
+      "version": "1.56.1",
+      "resolved": "https://registry.npmjs.org/playwright/-/playwright-1.56.1.tgz",
+      "integrity": "sha512-aFi5B0WovBHTEvpM3DzXTUaeN6eN0qWnTkKx4NQaH4Wvcmc153PdaY2UBdSYKaGYw+UyWXSVyxDUg5DoPEttjw==",
       "dev": true,
       "license": "Apache-2.0",
       "dependencies": {
-        "playwright-core": "1.47.2"
+        "playwright-core": "1.56.1"
       },
       "bin": {
         "playwright": "cli.js"
@@ -4324,9 +4324,9 @@
       }
     },
     "node_modules/playwright-core": {
-      "version": "1.47.2",
-      "resolved": "https://registry.npmjs.org/playwright-core/-/playwright-core-1.47.2.tgz",
-      "integrity": "sha512-3JvMfF+9LJfe16l7AbSmU555PaTl2tPyQsVInqm3id16pdDfvZ8TTZ/pyzmkbDrZTQefyzU7AIHlZqQnxpqHVQ==",
+      "version": "1.56.1",
+      "resolved": "https://registry.npmjs.org/playwright-core/-/playwright-core-1.56.1.tgz",
+      "integrity": "sha512-hutraynyn31F+Bifme+Ps9Vq59hKuUCz7H1kDOcBs+2oGguKkWTU50bBWrtz34OUWmIwpBTWDxaRPXrIXkgvmQ==",
       "dev": true,
       "license": "Apache-2.0",
       "bin": {
diff --git a/test/package.json b/test/package.json
index 6d2e92edd2ee..c8211337a79c 100644
--- a/test/package.json
+++ b/test/package.json
@@ -3,7 +3,7 @@
   "#": "We must put jest in a sub-directory otherwise VS Code somehow picks up the types and generates conflicts with mocha.",
   "devDependencies": {
     "@jest-mock/express": "^1.4.5",
-    "@playwright/test": "^1.46.0",
+    "@playwright/test": "^1.56.1",
     "@types/jest": "^27.0.2",
     "@types/jsdom": "^16.2.13",
     "@types/node-fetch": "^2.5.8",
@@ -14,7 +14,7 @@
     "jest-fetch-mock": "^3.0.3",
     "jsdom": "^16.4.0",
     "node-fetch": "^2.6.7",
-    "playwright": "^1.46.0",
+    "playwright": "^1.56.1",
     "ts-jest": "^27.0.7",
     "wtfnode": "^0.9.1"
   },
diff --git a/test/unit/node/heart.test.ts b/test/unit/node/heart.test.ts
index 7aa6f08dc2bf..7ad0d21752f2 100644
--- a/test/unit/node/heart.test.ts
+++ b/test/unit/node/heart.test.ts
@@ -1,6 +1,6 @@
 import { logger } from "@coder/logger"
 import { readFile, writeFile, stat, utimes } from "fs/promises"
-import { Heart, heartbeatTimer } from "../../../src/node/heart"
+import { Heart } from "../../../src/node/heart"
 import { clean, mockLogger, tmpdir } from "../../utils/helpers"
 
 const mockIsActive = (resolveTo: boolean) => jest.fn().mockResolvedValue(resolveTo)
@@ -82,31 +82,81 @@ describe("Heart", () => {
 })
 
 describe("heartbeatTimer", () => {
-  beforeAll(() => {
+  const testName = "heartbeatTimer"
+  let testDir = ""
+  beforeAll(async () => {
+    await clean(testName)
+    testDir = await tmpdir(testName)
     mockLogger()
   })
   afterAll(() => {
     jest.restoreAllMocks()
   })
+  beforeEach(() => {
+    jest.useFakeTimers()
+  })
   afterEach(() => {
     jest.resetAllMocks()
+    jest.clearAllTimers()
+    jest.useRealTimers()
   })
-  it("should call beat when isActive resolves to true", async () => {
+  it("should call isActive when timeout expires", async () => {
     const isActive = true
     const mockIsActive = jest.fn().mockResolvedValue(isActive)
-    const mockBeatFn = jest.fn()
-    await heartbeatTimer(mockIsActive, mockBeatFn)
+    const heart = new Heart(`${testDir}/shutdown.txt`, mockIsActive)
+    await heart.beat()
+    jest.advanceTimersByTime(60 * 1000)
     expect(mockIsActive).toHaveBeenCalled()
-    expect(mockBeatFn).toHaveBeenCalled()
   })
   it("should log a warning when isActive rejects", async () => {
     const errorMsg = "oh no"
     const error = new Error(errorMsg)
     const mockIsActive = jest.fn().mockRejectedValue(error)
-    const mockBeatFn = jest.fn()
-    await heartbeatTimer(mockIsActive, mockBeatFn)
+    const heart = new Heart(`${testDir}/shutdown.txt`, mockIsActive)
+    await heart.beat()
+    jest.advanceTimersByTime(60 * 1000)
+
     expect(mockIsActive).toHaveBeenCalled()
-    expect(mockBeatFn).not.toHaveBeenCalled()
     expect(logger.warn).toHaveBeenCalledWith(errorMsg)
   })
 })
+
+describe("stateChange", () => {
+  const testName = "stateChange"
+  let testDir = ""
+  let heart: Heart
+  beforeAll(async () => {
+    await clean(testName)
+    testDir = await tmpdir(testName)
+    mockLogger()
+  })
+  afterAll(() => {
+    jest.restoreAllMocks()
+  })
+  afterEach(() => {
+    jest.resetAllMocks()
+    if (heart) {
+      heart.dispose()
+    }
+  })
+  it("should change to alive after a beat", async () => {
+    heart = new Heart(`${testDir}/shutdown.txt`, mockIsActive(true))
+    const mockOnChange = jest.fn()
+    heart.onChange(mockOnChange)
+    await heart.beat()
+
+    expect(mockOnChange.mock.calls[0][0]).toBe("alive")
+  })
+  it.only("should change to expired when not active", async () => {
+    jest.useFakeTimers()
+    heart = new Heart(`${testDir}/shutdown.txt`, () => new Promise((resolve) => resolve(false)))
+    const mockOnChange = jest.fn()
+    heart.onChange(mockOnChange)
+    await heart.beat()
+
+    await jest.advanceTimersByTime(60 * 1000)
+    expect(mockOnChange.mock.calls[1][0]).toBe("expired")
+    jest.clearAllTimers()
+    jest.useRealTimers()
+  })
+})
diff --git a/test/unit/node/main.test.ts b/test/unit/node/main.test.ts
index 09ee6b512ef9..39ba2ca8bf9b 100644
--- a/test/unit/node/main.test.ts
+++ b/test/unit/node/main.test.ts
@@ -16,6 +16,7 @@ jest.mock("@coder/logger", () => ({
     debug: jest.fn(),
     warn: jest.fn(),
     error: jest.fn(),
+    named: jest.fn(),
     level: 0,
   },
   field: jest.fn(),
@@ -94,7 +95,7 @@ describe("main", () => {
 
       // Mock routes module
       jest.doMock("../../../src/node/routes", () => ({
-        register: jest.fn().mockResolvedValue(jest.fn()),
+        register: jest.fn().mockResolvedValue({ disposeRoutes: jest.fn() }),
       }))
 
       // Mock loadCustomStrings to succeed
@@ -131,7 +132,7 @@ describe("main", () => {
 
       // Mock routes module
       jest.doMock("../../../src/node/routes", () => ({
-        register: jest.fn().mockResolvedValue(jest.fn()),
+        register: jest.fn().mockResolvedValue({ disposeRoutes: jest.fn() }),
       }))
 
       // Import runCodeServer after mocking