diff --git a/package.json b/package.json
index f289862c68..20a95b5fe7 100644
--- a/package.json
+++ b/package.json
@@ -304,6 +304,7 @@
     "@types/tar": "^4.0.5",
     "@types/tcp-port-used": "^1.0.0",
     "@types/tempy": "^0.3.0",
+    "@types/triple-beam": "^1.3.2",
     "@types/url-parse": "^1.4.3",
     "@types/uuid": "^8.3.0",
     "@types/webdriverio": "^4.13.0",
diff --git a/src/common/sentry.ts b/src/common/sentry.ts
index da0e749994..06bef321d1 100644
--- a/src/common/sentry.ts
+++ b/src/common/sentry.ts
@@ -23,7 +23,7 @@ import { CaptureConsole, Dedupe, Offline } from "@sentry/integrations";
 import * as Sentry from "@sentry/electron";
 import { sentryDsn, isProduction } from "./vars";
 import { UserStore } from "./user-store";
-import logger from "../main/logger";
+import { inspect } from "util";
 
 /**
  * "Translate" 'browser' to 'main' as Lens developer more familiar with the term 'main'
@@ -51,10 +51,13 @@ export function SentryInit() {
         return event;
       }
 
-      logger.info(`🔒  [SENTRY-BEFORE-SEND-HOOK]: allowErrorReporting: ${allowErrorReporting}. Sentry event is caught but not sent to server.`);
-      logger.info("🔒  [SENTRY-BEFORE-SEND-HOOK]: === START OF SENTRY EVENT ===");
-      logger.info(event);
-      logger.info("🔒  [SENTRY-BEFORE-SEND-HOOK]: ===  END OF SENTRY EVENT  ===");
+      /**
+       * Directly write to stdout so that no other integrations capture this and create an infinite loop
+       */
+      process.stdout.write(`🔒  [SENTRY-BEFORE-SEND-HOOK]: allowErrorReporting: ${allowErrorReporting}. Sentry event is caught but not sent to server.`);
+      process.stdout.write("🔒  [SENTRY-BEFORE-SEND-HOOK]: === START OF SENTRY EVENT ===");
+      process.stdout.write(inspect(event, false, null, true));
+      process.stdout.write("🔒  [SENTRY-BEFORE-SEND-HOOK]: ===  END OF SENTRY EVENT  ===");
 
       // if return null, the event won't be sent
       // ref https://github.com/getsentry/sentry-javascript/issues/2039
@@ -64,12 +67,11 @@ export function SentryInit() {
     integrations: [
       new CaptureConsole({ levels: ["error"] }),
       new Dedupe(),
-      new Offline()
+      new Offline(),
     ],
     initialScope: {
       tags: {
-
-        "process": processName
+        "process": processName,
       }
     },
     environment: isProduction ? "production" : "development",
diff --git a/src/main/logger.ts b/src/main/logger.ts
index 89a0ede7f0..ffa695ac2e 100644
--- a/src/main/logger.ts
+++ b/src/main/logger.ts
@@ -21,31 +21,93 @@
 
 import { app, remote } from "electron";
 import winston from "winston";
+import Transport from "winston-transport";
 import { isDebugging, isTestEnv } from "../common/vars";
+import { LEVEL } from "triple-beam";
+import { Severity } from "@sentry/browser";
+import * as Sentry from "@sentry/electron";
 
-const logLevel = process.env.LOG_LEVEL ? process.env.LOG_LEVEL : isDebugging ? "debug" : "info";
-const consoleOptions: winston.transports.ConsoleTransportOptions = {
-  handleExceptions: false,
-  level: logLevel,
+const SENTRY_LEVELS_MAP = {
+  silly: Severity.Debug,
+  verbose: Severity.Debug,
+  debug: Severity.Debug,
+  info: Severity.Info,
+  warn: Severity.Warning,
+  error: Severity.Error,
 };
-const fileOptions: winston.transports.FileTransportOptions = {
-  handleExceptions: false,
-  level: logLevel,
-  filename: "lens.log",
-  dirname: (app ?? remote?.app)?.getPath("logs"),
-  maxsize: 16 * 1024,
-  maxFiles: 16,
-  tailable: true,
+const WINSTON_CMP: Record<WinstonLevel, Set<WinstonLevel>> = {
+  silly: new Set(["silly", "verbose", "debug", "info", "warn", "error"]),
+  verbose: new Set(["verbose", "debug", "info", "warn", "error"]),
+  debug: new Set(["debug", "info", "warn", "error"]),
+  info: new Set(["info", "warn", "error"]),
+  warn: new Set(["warn", "error"]),
+  error: new Set(["error"]),
 };
-const logger = winston.createLogger({
+
+type WinstonLevel = keyof typeof SENTRY_LEVELS_MAP;
+
+class SentryTransport extends Transport {
+  logLevels: Set<WinstonLevel>;
+
+  constructor(minWinstonLevel: WinstonLevel) {
+    super();
+
+    this.logLevels = WINSTON_CMP[minWinstonLevel];
+  }
+
+  log(info: any, next: () => void) {
+    setImmediate(() => {
+      this.emit("logged", info);
+    });
+
+    const { message, level: _, tags, user, ...extra } = info;
+    const winstonLevel: WinstonLevel = info[LEVEL];
+    const level = SENTRY_LEVELS_MAP[winstonLevel];
+
+    try {
+      if (this.logLevels.has(winstonLevel)) {
+        Sentry.captureMessage(message, {
+          level,
+          tags,
+          extra,
+        });
+      }
+    } finally {
+      next();
+    }
+  }
+}
+
+interface CreateLoggerOpts extends winston.LoggerOptions {
+  transports?: Transport[];
+}
+
+const logLevel = process.env.LOG_LEVEL || (isDebugging ? "debug" : "info");
+
+const loggerOpts: CreateLoggerOpts = {
   format: winston.format.combine(
     winston.format.colorize(),
     winston.format.simple(),
   ),
   transports: [
-    new winston.transports.Console(consoleOptions),
-    ...(isTestEnv ? [] : [new winston.transports.File(fileOptions)]),
+    new SentryTransport("error"),
+    new winston.transports.Console({
+      handleExceptions: false,
+      level: logLevel,
+    }),
   ],
-});
+};
 
-export default logger;
+if (!isTestEnv) {
+  loggerOpts.transports.push(new winston.transports.File({
+    handleExceptions: false,
+    level: logLevel,
+    filename: "lens.log",
+    dirname: (app ?? remote?.app)?.getPath("logs"),
+    maxsize: 16 * 1024,
+    maxFiles: 16,
+    tailable: true,
+  }));
+}
+
+export default winston.createLogger(loggerOpts);
diff --git a/yarn.lock b/yarn.lock
index dc2c28ce88..f6d70866db 100644
--- a/yarn.lock
+++ b/yarn.lock
@@ -2010,6 +2010,11 @@
   resolved "https://registry.yarnpkg.com/@types/tough-cookie/-/tough-cookie-4.0.0.tgz#fef1904e4668b6e5ecee60c52cc6a078ffa6697d"
   integrity sha512-I99sngh224D0M7XgW1s120zxCt3VYQ3IQsuw3P3jbq5GG4yc79+ZjyKznyOGIQrflfylLgcfekeZW/vk0yng6A==
 
+"@types/triple-beam@^1.3.2":
+  version "1.3.2"
+  resolved "https://registry.yarnpkg.com/@types/triple-beam/-/triple-beam-1.3.2.tgz#38ecb64f01aa0d02b7c8f4222d7c38af6316fef8"
+  integrity sha512-txGIh+0eDFzKGC25zORnswy+br1Ha7hj5cMVwKIU7+s0U2AxxJru/jZSMU6OC9MJWP6+pc/hc6ZjyZShpsyY2g==
+
 "@types/trusted-types@*":
   version "1.0.4"
   resolved "https://registry.yarnpkg.com/@types/trusted-types/-/trusted-types-1.0.4.tgz#922d092c84a776a59acb0bd6785fd82b59b9bad5"