diff --git a/.cirrus.yml b/.cirrus.yml
index 1352be767..e838d93fc 100644
--- a/.cirrus.yml
+++ b/.cirrus.yml
@@ -14,6 +14,7 @@ env:
   ARTIFACTORY_DEPLOY_REPO: sonarsource-public-qa
   NPM_CONFIG_registry: https://repox.jfrog.io/artifactory/api/npm/npm
   NPM_CONFIG_//repox.jfrog.io/artifactory/api/npm/:_authToken: VAULT[development/artifactory/token/${CIRRUS_REPO_OWNER}-${CIRRUS_REPO_NAME}-private-reader access_token]
+  SENTRY_UPLOAD_TOKEN: VAULT[development/kv/data/sentry/sq-ide-upload data.token]
 
   ARTIFACTORY_PRIVATE_READER_USERNAME: $ARTIFACTORY_PRIVATE_USERNAME
   ARTIFACTORY_PRIVATE_READER_PASSWORD: $ARTIFACTORY_PRIVATE_PASSWORD
diff --git a/build-sonarlint/deployUtils.mjs b/build-sonarlint/deployUtils.mjs
index ad561aeff..c160c64d6 100644
--- a/build-sonarlint/deployUtils.mjs
+++ b/build-sonarlint/deployUtils.mjs
@@ -10,7 +10,7 @@ import { getPackageJSON } from './fsUtils.mjs';
 import { join, extname, basename } from 'path';
 import dateformat from 'dateformat';
 import { computeDependencyHashes, fileHashsum } from './hashes.mjs';
-import jarDependencies from '../scripts/dependencies.json' assert { type: "json" } ;
+import jarDependencies from '../scripts/dependencies.json' with { type: "json" } ;
 import { createReadStream } from 'fs';
 import fetch, { Headers } from 'node-fetch';
 import { globbySync } from 'globby';
diff --git a/its/userdir/User/settings.json b/its/userdir/User/settings.json
index ed41f9377..12ad97e90 100644
--- a/its/userdir/User/settings.json
+++ b/its/userdir/User/settings.json
@@ -14,7 +14,7 @@
   // Enable auto import of Git repositories
   "git.openRepositoryInParentFolders": "always",
   // Disable SonarLint product telemetry in ITs
-  "sonarlint.ls.vmargs": " -Dsonarlint.telemetry.disabled=true ",
+  "sonarlint.ls.vmargs": " -Dsonarlint.telemetry.disabled=true -Dsonarlint.monitoring.disabled=true ",
   "sonarlint.output.showAnalyzerLogs": true,
   "sonarlint.output.showVerboseLogs": true
 }
diff --git a/package-lock.json b/package-lock.json
index 949fee6e0..5c1870fc2 100644
--- a/package-lock.json
+++ b/package-lock.json
@@ -9,6 +9,7 @@
       "version": "4.15.0-SNAPSHOT",
       "license": "SEE LICENSE IN LICENSE.txt",
       "dependencies": {
+        "@sentry/node": "^8.44.0",
         "@vscode/webview-ui-toolkit": "1.0.0",
         "@xmldom/xmldom": "^0.9.6",
         "compare-versions": "4.1.3",
@@ -33,12 +34,13 @@
       },
       "devDependencies": {
         "@cyclonedx/bom": "^4.1.0",
+        "@sentry/webpack-plugin": "^2.22.7",
         "@types/chai": "^4.3.9",
         "@types/follow-redirects": "^1.14.4",
         "@types/lodash": "^4.14.194",
         "@types/luxon": "^3.2.0",
         "@types/mocha": "^10.0.10",
-        "@types/node": "^10.17.17",
+        "@types/node": "^22.9.3",
         "@types/vscode": "^1.73.1",
         "@vscode/test-electron": "^2.4.1",
         "@vscode/vsce": "2.21.1",
@@ -938,13 +940,918 @@
         "node": ">=8.0"
       }
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+      "version": "1.9.0",
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@@ -4553,6 +5574,12 @@
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       "version": "2.1.3",
       "resolved": "https://repox.jfrog.io/artifactory/api/npm/npm/ms/-/ms-2.1.3.tgz",
-      "integrity": "sha512-6FlzubTLZG3J2a/NVCAleEhjzq5oxgHyaCU9yYXvcLsvoVaHJq/s5xXI6/XXP6tz7R9xAOtHnSO/tXtF3WRTlA==",
-      "dev": true
+      "integrity": "sha512-6FlzubTLZG3J2a/NVCAleEhjzq5oxgHyaCU9yYXvcLsvoVaHJq/s5xXI6/XXP6tz7R9xAOtHnSO/tXtF3WRTlA=="
     },
     "node_modules/mute-stream": {
       "version": "0.0.8",
@@ -5150,7 +6176,6 @@
       "version": "1.0.7",
       "resolved": "https://repox.jfrog.io/artifactory/api/npm/npm/path-parse/-/path-parse-1.0.7.tgz",
       "integrity": "sha512-LDJzPVEEEPR+y48z93A0Ed0yXb8pAByGWo/k5YYdYgpY2/2EsOsksJrq7lOHxryrVOn1ejG6oAp8ahvOIQD8sw==",
-      "dev": true,
       "license": "MIT"
     },
     "node_modules/path-scurry": {
@@ -5220,6 +6245,37 @@
       "resolved": "https://repox.jfrog.io/artifactory/api/npm/npm/pend/-/pend-1.2.0.tgz",
       "integrity": "sha512-F3asv42UuXchdzt+xXqfW1OGlVBe+mxa2mqI0pg5yAHZPvFmY3Y6drSf/GQ1A86WgWEN9Kzh/WrgKa6iGcHXLg=="
     },
+    "node_modules/pg-int8": {
+      "version": "1.0.1",
+      "resolved": "https://repox.jfrog.io/artifactory/api/npm/npm/pg-int8/-/pg-int8-1.0.1.tgz",
+      "integrity": "sha512-WCtabS6t3c8SkpDBUlb1kjOs7l66xsGdKpIPZsg4wR+B3+u9UAum2odSsF9tnvxg80h4ZxLWMy4pRjOsFIqQpw==",
+      "license": "ISC",
+      "engines": {
+        "node": ">=4.0.0"
+      }
+    },
+    "node_modules/pg-protocol": {
+      "version": "1.7.0",
+      "resolved": "https://repox.jfrog.io/artifactory/api/npm/npm/pg-protocol/-/pg-protocol-1.7.0.tgz",
+      "integrity": "sha512-hTK/mE36i8fDDhgDFjy6xNOG+LCorxLG3WO17tku+ij6sVHXh1jQUJ8hYAnRhNla4QVD2H8er/FOjc/+EgC6yQ==",
+      "license": "MIT"
+    },
+    "node_modules/pg-types": {
+      "version": "2.2.0",
+      "resolved": "https://repox.jfrog.io/artifactory/api/npm/npm/pg-types/-/pg-types-2.2.0.tgz",
+      "integrity": "sha512-qTAAlrEsl8s4OiEQY69wDvcMIdQN6wdz5ojQiOy6YRMuynxenON0O5oCpJI6lshc6scgAY8qvJ2On/p+CXY0GA==",
+      "license": "MIT",
+      "dependencies": {
+        "pg-int8": "1.0.1",
+        "postgres-array": "~2.0.0",
+        "postgres-bytea": "~1.0.0",
+        "postgres-date": "~1.0.4",
+        "postgres-interval": "^1.1.0"
+      },
+      "engines": {
+        "node": ">=4"
+      }
+    },
     "node_modules/picocolors": {
       "version": "1.0.0",
       "resolved": "https://repox.jfrog.io/artifactory/api/npm/npm/picocolors/-/picocolors-1.0.0.tgz",
@@ -5333,6 +6389,45 @@
         "node": ">=8"
       }
     },
+    "node_modules/postgres-array": {
+      "version": "2.0.0",
+      "resolved": "https://repox.jfrog.io/artifactory/api/npm/npm/postgres-array/-/postgres-array-2.0.0.tgz",
+      "integrity": "sha512-VpZrUqU5A69eQyW2c5CA1jtLecCsN2U/bD6VilrFDWq5+5UIEVO7nazS3TEcHf1zuPYO/sqGvUvW62g86RXZuA==",
+      "license": "MIT",
+      "engines": {
+        "node": ">=4"
+      }
+    },
+    "node_modules/postgres-bytea": {
+      "version": "1.0.0",
+      "resolved": "https://repox.jfrog.io/artifactory/api/npm/npm/postgres-bytea/-/postgres-bytea-1.0.0.tgz",
+      "integrity": "sha512-xy3pmLuQqRBZBXDULy7KbaitYqLcmxigw14Q5sj8QBVLqEwXfeybIKVWiqAXTlcvdvb0+xkOtDbfQMOf4lST1w==",
+      "license": "MIT",
+      "engines": {
+        "node": ">=0.10.0"
+      }
+    },
+    "node_modules/postgres-date": {
+      "version": "1.0.7",
+      "resolved": "https://repox.jfrog.io/artifactory/api/npm/npm/postgres-date/-/postgres-date-1.0.7.tgz",
+      "integrity": "sha512-suDmjLVQg78nMK2UZ454hAG+OAW+HQPZ6n++TNDUX+L0+uUlLywnoxJKDou51Zm+zTCjrCl0Nq6J9C5hP9vK/Q==",
+      "license": "MIT",
+      "engines": {
+        "node": ">=0.10.0"
+      }
+    },
+    "node_modules/postgres-interval": {
+      "version": "1.2.0",
+      "resolved": "https://repox.jfrog.io/artifactory/api/npm/npm/postgres-interval/-/postgres-interval-1.2.0.tgz",
+      "integrity": "sha512-9ZhXKM/rw350N1ovuWHbGxnGh/SNJ4cnxHiM0rxE4VN41wsg8P8zWn9hv/buK00RP4WvlOyr/RBDiptyxVbkZQ==",
+      "license": "MIT",
+      "dependencies": {
+        "xtend": "^4.0.0"
+      },
+      "engines": {
+        "node": ">=0.10.0"
+      }
+    },
     "node_modules/prebuild-install": {
       "version": "7.1.1",
       "resolved": "https://repox.jfrog.io/artifactory/api/npm/npm/prebuild-install/-/prebuild-install-7.1.1.tgz",
@@ -5377,6 +6472,16 @@
       "resolved": "https://repox.jfrog.io/artifactory/api/npm/npm/process-nextick-args/-/process-nextick-args-2.0.1.tgz",
       "integrity": "sha512-3ouUOpQhtgrbOa17J7+uxOTpITYWaGP7/AhoR3+A+/1e9skrzelGi/dXzEYyvbxubEF6Wn2ypscTKiKJFFn1ag=="
     },
+    "node_modules/progress": {
+      "version": "2.0.3",
+      "resolved": "https://repox.jfrog.io/artifactory/api/npm/npm/progress/-/progress-2.0.3.tgz",
+      "integrity": "sha512-7PiHtLll5LdnKIMw100I+8xJXR5gW2QwWYkT6iJva0bXitZKa/XMrSbdmg3r2Xnaidz9Qumd0VPaMrZlF9V9sA==",
+      "dev": true,
+      "license": "MIT",
+      "engines": {
+        "node": ">=0.4.0"
+      }
+    },
     "node_modules/properties": {
       "version": "1.2.1",
       "resolved": "https://repox.jfrog.io/artifactory/api/npm/npm/properties/-/properties-1.2.1.tgz",
@@ -5613,11 +6718,24 @@
         "node": ">=0.10.0"
       }
     },
+    "node_modules/require-in-the-middle": {
+      "version": "7.4.0",
+      "resolved": "https://repox.jfrog.io/artifactory/api/npm/npm/require-in-the-middle/-/require-in-the-middle-7.4.0.tgz",
+      "integrity": "sha512-X34iHADNbNDfr6OTStIAHWSAvvKQRYgLO6duASaVf7J2VA3lvmNYboAHOuLC2huav1IwgZJtyEcJCKVzFxOSMQ==",
+      "license": "MIT",
+      "dependencies": {
+        "debug": "^4.3.5",
+        "module-details-from-path": "^1.0.3",
+        "resolve": "^1.22.8"
+      },
+      "engines": {
+        "node": ">=8.6.0"
+      }
+    },
     "node_modules/resolve": {
       "version": "1.22.8",
       "resolved": "https://repox.jfrog.io/artifactory/api/npm/npm/resolve/-/resolve-1.22.8.tgz",
       "integrity": "sha512-oKWePCxqpd6FlLvGV1VU0x7bkPmmCNolxzjMf4NczoDnQcIWrAF+cPtZn5i6n+RfD2d9i0tzpKnG6Yk168yIyw==",
-      "dev": true,
       "license": "MIT",
       "dependencies": {
         "is-core-module": "^2.13.0",
@@ -5900,6 +7018,12 @@
         "node": ">=8"
       }
     },
+    "node_modules/shimmer": {
+      "version": "1.2.1",
+      "resolved": "https://repox.jfrog.io/artifactory/api/npm/npm/shimmer/-/shimmer-1.2.1.tgz",
+      "integrity": "sha512-sQTKC1Re/rM6XyFM6fIAGHRPVGvyXfgzIDvzoq608vM+jeyVD0Tu1E6Np0Kc2zAIFWIj963V2800iF/9LPieQw==",
+      "license": "BSD-2-Clause"
+    },
     "node_modules/side-channel": {
       "version": "1.0.4",
       "resolved": "https://repox.jfrog.io/artifactory/api/npm/npm/side-channel/-/side-channel-1.0.4.tgz",
@@ -6312,7 +7436,6 @@
       "version": "1.0.0",
       "resolved": "https://repox.jfrog.io/artifactory/api/npm/npm/supports-preserve-symlinks-flag/-/supports-preserve-symlinks-flag-1.0.0.tgz",
       "integrity": "sha512-ot0WnXS9fgdkgIcePe6RHNk1WA8+muPa6cSjeR3V8K27q9BB1rTE3R1p7Hv0z1ZyAc8s6Vvv8DIyWf681MAt0w==",
-      "dev": true,
       "license": "MIT",
       "engines": {
         "node": ">= 0.4"
@@ -6774,6 +7897,12 @@
       "resolved": "https://repox.jfrog.io/artifactory/api/npm/npm/underscore/-/underscore-1.13.6.tgz",
       "integrity": "sha512-+A5Sja4HP1M08MaXya7p5LvjuM7K6q/2EaC0+iovj/wOcMsTzMvDFbasi/oSapiwOlt252IqsKqPjCl7huKS0A=="
     },
+    "node_modules/undici-types": {
+      "version": "6.20.0",
+      "resolved": "https://repox.jfrog.io/artifactory/api/npm/npm/undici-types/-/undici-types-6.20.0.tgz",
+      "integrity": "sha512-Ny6QZ2Nju20vw1SRHe3d9jVu6gJ+4e3+MMpqu7pqE5HT6WsTSlce++GQmK5UXS8mzV8DSYHrQH+Xrf2jVcuKNg==",
+      "license": "MIT"
+    },
     "node_modules/unicorn-magic": {
       "version": "0.1.0",
       "resolved": "https://repox.jfrog.io/artifactory/api/npm/npm/unicorn-magic/-/unicorn-magic-0.1.0.tgz",
@@ -6794,6 +7923,19 @@
         "node": ">= 10.0.0"
       }
     },
+    "node_modules/unplugin": {
+      "version": "1.0.1",
+      "resolved": "https://repox.jfrog.io/artifactory/api/npm/npm/unplugin/-/unplugin-1.0.1.tgz",
+      "integrity": "sha512-aqrHaVBWW1JVKBHmGo33T5TxeL0qWzfvjWokObHA9bYmN7eNDkwOxmLjhioHl9878qDFMAaT51XNroRyuz7WxA==",
+      "dev": true,
+      "license": "MIT",
+      "dependencies": {
+        "acorn": "^8.8.1",
+        "chokidar": "^3.5.3",
+        "webpack-sources": "^3.2.3",
+        "webpack-virtual-modules": "^0.5.0"
+      }
+    },
     "node_modules/unzipper": {
       "version": "0.12.3",
       "resolved": "https://repox.jfrog.io/artifactory/api/npm/npm/unzipper/-/unzipper-0.12.3.tgz",
@@ -6844,6 +7986,20 @@
       "resolved": "https://repox.jfrog.io/artifactory/api/npm/npm/util-deprecate/-/util-deprecate-1.0.2.tgz",
       "integrity": "sha512-EPD5q1uXyFxJpCrLnCc1nHnq3gOa6DZBocAIiI2TaSCA7VCJ1UJDMagCzIkXNsUYfD1daK//LTEQ8xiIbrHtcw=="
     },
+    "node_modules/uuid": {
+      "version": "9.0.1",
+      "resolved": "https://repox.jfrog.io/artifactory/api/npm/npm/uuid/-/uuid-9.0.1.tgz",
+      "integrity": "sha512-b+1eJOlsR9K8HJpow9Ok3fiWOWSIcIzXodvv0rQjVoOVNpWMpxf1wZNpt4y9h10odCNrqnYp1OBzRktckBe3sA==",
+      "dev": true,
+      "funding": [
+        "https://github.com/sponsors/broofa",
+        "https://github.com/sponsors/ctavan"
+      ],
+      "license": "MIT",
+      "bin": {
+        "uuid": "dist/bin/uuid"
+      }
+    },
     "node_modules/validate-npm-package-license": {
       "version": "3.0.4",
       "resolved": "https://repox.jfrog.io/artifactory/api/npm/npm/validate-npm-package-license/-/validate-npm-package-license-3.0.4.tgz",
@@ -7064,6 +8220,13 @@
         "node": ">=10.13.0"
       }
     },
+    "node_modules/webpack-virtual-modules": {
+      "version": "0.5.0",
+      "resolved": "https://repox.jfrog.io/artifactory/api/npm/npm/webpack-virtual-modules/-/webpack-virtual-modules-0.5.0.tgz",
+      "integrity": "sha512-kyDivFZ7ZM0BVOUteVbDFhlRt7Ah/CSPwJdi8hBpkK7QLumUqdLtVfm/PX/hkcnrvr0i77fO5+TjZ94Pe+C9iw==",
+      "dev": true,
+      "license": "MIT"
+    },
     "node_modules/whatwg-url": {
       "version": "5.0.0",
       "resolved": "https://repox.jfrog.io/artifactory/api/npm/npm/whatwg-url/-/whatwg-url-5.0.0.tgz",
diff --git a/package.json b/package.json
index 050d070f7..0fc1d2a0a 100644
--- a/package.json
+++ b/package.json
@@ -541,6 +541,11 @@
         "category": "SonarQube",
         "icon": "$(export)",
         "enablement": "view == SonarLint.ConnectedMode"
+      },
+      {
+        "command": "SonarLint.CheckMonitoring",
+        "title": "Send A Monitoring Event",
+        "category": "SonarQube"
       }
     ],
     "viewsContainers": {
@@ -867,7 +872,9 @@
     "package-all": "node build-sonarlint/package-all.mjs"
   },
   "dependencies": {
+    "@sentry/node": "^8.44.0",
     "@vscode/webview-ui-toolkit": "1.0.0",
+    "@xmldom/xmldom": "^0.9.6",
     "compare-versions": "4.1.3",
     "diff": "^5.1.0",
     "expand-home-dir": "0.0.3",
@@ -886,17 +893,17 @@
     "tar": "^7.4.3",
     "underscore": "^1.13.6",
     "vscode-languageclient": "^8.0.2",
-    "@xmldom/xmldom": "^0.9.6",
     "zlib": "^1.0.5"
   },
   "devDependencies": {
     "@cyclonedx/bom": "^4.1.0",
+    "@sentry/webpack-plugin": "^2.22.7",
     "@types/chai": "^4.3.9",
     "@types/follow-redirects": "^1.14.4",
     "@types/lodash": "^4.14.194",
     "@types/luxon": "^3.2.0",
     "@types/mocha": "^10.0.10",
-    "@types/node": "^10.17.17",
+    "@types/node": "^22.9.3",
     "@types/vscode": "^1.73.1",
     "@vscode/test-electron": "^2.4.1",
     "@vscode/vsce": "2.21.1",
@@ -923,10 +930,10 @@
     "through2": "^2.0.5",
     "ts-loader": "^9.5.1",
     "typescript": "^4.9.5",
+    "unzipper": "^0.12.3",
     "vinyl": "^2.2.1",
     "webpack": "^5.94.0",
-    "webpack-cli": "^5.1.4",
-    "unzipper": "^0.12.3"
+    "webpack-cli": "^5.1.4"
   },
   "prettier": {
     "jsxBracketSameLine": true,
diff --git a/scripts/dependencies.json b/scripts/dependencies.json
index 5eac01c51..00dc2c525 100644
--- a/scripts/dependencies.json
+++ b/scripts/dependencies.json
@@ -2,7 +2,7 @@
   {
     "groupId": "org.sonarsource.sonarlint.ls",
     "artifactId": "sonarlint-language-server",
-    "version": "3.15.0.75834",
+    "version": "3.15.0.75832",
     "output": "server/sonarlint-ls.jar"
   },
   {
diff --git a/src/extension.ts b/src/extension.ts
index e9ad8d7be..35a508cf2 100644
--- a/src/extension.ts
+++ b/src/extension.ts
@@ -5,6 +5,10 @@
  * Licensed under the LGPLv3 License. See LICENSE.txt in the project root for license information.
  * ------------------------------------------------------------------------------------------ */
 'use strict';
+
+// Must be kept at the top for Node instrumentation to work correctly
+import { withMonitoring } from './monitoring/monitoring';
+
 import * as ChildProcess from 'child_process';
 import { DateTime } from 'luxon';
 import * as Path from 'path';
@@ -154,6 +158,7 @@ export async function activate(context: VSCode.ExtensionContext) {
     installTime = new Date().toISOString();
     context.globalState.update(installTimeKey, installTime);
   }
+
   loadInitialSettings();
   util.setExtensionContext(context);
   initLogOutput(context);
@@ -352,6 +357,14 @@ function suggestBinding(params: protocol.SuggestBindingParams) {
 }
 
 function registerCommands(context: VSCode.ExtensionContext) {
+  function checkMonitoring () {
+    throw new Error('Test from a command handler');
+  }
+
+  context.subscriptions.push(
+    VSCode.commands.registerCommand('SonarLint.CheckMonitoring', () => withMonitoring(checkMonitoring))
+  );
+
   context.subscriptions.push(
     VSCode.commands.registerCommand('SonarLint.OpenSample', async () => {
       const sampleFileUri = VSCode.Uri.joinPath(context.extensionUri, 'walkthrough', 'sample.py');
diff --git a/src/lsp/server.ts b/src/lsp/server.ts
index 706281167..6f98debf5 100644
--- a/src/lsp/server.ts
+++ b/src/lsp/server.ts
@@ -26,6 +26,7 @@ export function languageServerCommand(
   if (DEBUG) {
     params.push('-agentlib:jdwp=transport=dt_socket,server=y,suspend=n,address=8000,quiet=y');
     params.push('-Dsonarlint.telemetry.disabled=true');
+    params.push('-Dsonarlint.monitoring.disabled=true');
   }
   const vmargs = getSonarLintConfiguration().get('ls.vmargs', '');
   parseVMargs(params, vmargs);
diff --git a/src/monitoring/dogfooding.ts b/src/monitoring/dogfooding.ts
new file mode 100644
index 000000000..2ebdc37ea
--- /dev/null
+++ b/src/monitoring/dogfooding.ts
@@ -0,0 +1,11 @@
+/* --------------------------------------------------------------------------------------------
+ * SonarLint for VisualStudio Code
+ * Copyright (C) 2017-2024 SonarSource SA
+ * sonarlint@sonarsource.com
+ * Licensed under the LGPLv3 License. See LICENSE.txt in the project root for license information.
+ * ------------------------------------------------------------------------------------------ */
+'use strict';
+
+export function isDogfoodingEnvironment() {
+  return process.env.SONARSOURCE_DOGFOODING === '1';
+}
diff --git a/src/monitoring/monitoring.ts b/src/monitoring/monitoring.ts
new file mode 100644
index 000000000..dfc262c45
--- /dev/null
+++ b/src/monitoring/monitoring.ts
@@ -0,0 +1,84 @@
+/* --------------------------------------------------------------------------------------------
+ * SonarLint for VisualStudio Code
+ * Copyright (C) 2017-2024 SonarSource SA
+ * sonarlint@sonarsource.com
+ * Licensed under the LGPLv3 License. See LICENSE.txt in the project root for license information.
+ * ------------------------------------------------------------------------------------------ */
+'use strict';
+
+import * as process from 'process';
+import {
+  defaultStackParser,
+  getDefaultIntegrations,
+  NodeClient,
+  makeNodeTransport,
+  Scope, EventHint
+} from '@sentry/node';
+import * as vscode from 'vscode';
+
+import { isDogfoodingEnvironment } from './dogfooding';
+import * as util from '../util/util';
+
+const SKIPPED_DEFAULT_INTEGRATIONS = [
+  'Breadcrumbs',
+  'GlobalHandlers'
+];
+
+class MonitoringService {
+
+  public static readonly instance = new MonitoringService();
+  private readonly scope: Scope;
+
+  private constructor() {
+    if(isDogfoodingEnvironment()) {
+      console.info('Initializing monitoring service in dogfooding environment');
+
+      // Following the recommendations on shared environment, we're initializing our Sentry client manually
+      // to avoid catching events from other extensions or from the VSCode platform itself
+      // See: https://docs.sentry.io/platforms/javascript/best-practices/shared-environments/
+
+      // Filter integrations that use the global variable
+      const integrations = getDefaultIntegrations({}).filter(
+        (defaultIntegration) => {
+          return !SKIPPED_DEFAULT_INTEGRATIONS.includes(defaultIntegration.name);
+        },
+      );
+
+      const client = new NodeClient({
+        dsn: 'https://5e3853ab83d91a04bfc8d81347dadc14@o1316750.ingest.us.sentry.io/4508460058214400',
+        transport: makeNodeTransport,
+        stackParser: defaultStackParser,
+        integrations,
+        environment: 'dogfood',
+        release: util.packageJson.version,
+        beforeSend: (event, hint) => {
+          event.tags = {
+            productKey: 'vscode',
+            ideVersion: vscode.version,
+            architecture: process.arch,
+            ...event.tags
+          }
+          return event;
+        }
+      });
+
+      this.scope = new Scope();
+      this.scope.setClient(client);
+
+      client.init();
+    }
+  }
+
+  public captureException(exception: Error, hint?: EventHint) {
+    this.scope.captureException(exception, hint);
+  }
+}
+
+export function withMonitoring(wrapped: () => any) {
+  try {
+    return wrapped();
+  } catch (error) {
+    MonitoringService.instance.captureException(error);
+    throw error;
+  }
+}
diff --git a/test/userdir/User/settings.json b/test/userdir/User/settings.json
index eb7c190c0..c754a47b9 100644
--- a/test/userdir/User/settings.json
+++ b/test/userdir/User/settings.json
@@ -12,7 +12,7 @@
   "editor.suggestSelection": "first",
   "vsintellicode.modify.editor.suggestSelection": "automaticallyOverrodeDefaultValue",
   // Disable SonarLint product telemetry in ITs
-  "sonarlint.ls.vmargs": " -Dsonarlint.telemetry.disabled=true ",
+  "sonarlint.ls.vmargs": " -Dsonarlint.telemetry.disabled=true -Dsonarlint.monitoring.disabled=true ",
   // Enable auto import of Git repositories
   "git.openRepositoryInParentFolders": "always",
   "sonarlint.output.showAnalyzerLogs": true,
diff --git a/webpack.config.js b/webpack.config.js
index 15cb700d8..2849a6198 100644
--- a/webpack.config.js
+++ b/webpack.config.js
@@ -46,6 +46,36 @@ const config = {
         ]
       }
     ]
-  }
+  },
+  plugins: []
 };
-module.exports = config;
+
+module.exports = (env, argv) => {
+
+  if (
+    // Only for production builds (e.g. CI)
+    argv.mode === 'production' &&
+    // Injected by Vault
+    process.env.SENTRY_UPLOAD_TOKEN &&
+    // Injected by CI
+    process.env.BUILD_NUMBER
+  ) {
+    console.log('Enabling Sentry upload plugin');
+    /**@type {import('webpack').WebpackPluginFunction}*/
+    const { sentryWebpackPlugin } = require('@sentry/webpack-plugin');
+    const { version } = require('./package.json');
+
+    config.plugins.push(sentryWebpackPlugin({
+      org: 'sonar-x0',
+      project: 'sonarqube-vscode',
+      authToken: process.env.SENTRY_UPLOAD_TOKEN,
+      release: {
+        name: version
+      }
+    }));
+  } else {
+    console.log('Not enabling Sentry upload plugin');
+  }
+
+  return config;
+}