diff --git a/electron/helpers/config-file-reader.ts b/electron/helpers/config-file-reader.ts
index 5f61e43..1b29784 100644
--- a/electron/helpers/config-file-reader.ts
+++ b/electron/helpers/config-file-reader.ts
@@ -1,6 +1,6 @@
 import fs from "node:fs";
 
-import { Logging } from "../utils/logging";
+import { Logging, LogLevel } from "../utils/logging";
 
 export abstract class ConfigFileReader {
   static get(file: string, section: string, key: string) {
@@ -9,7 +9,10 @@ export abstract class ConfigFileReader {
     try {
       contents = fs.readFileSync(file, { encoding: "utf-8" });
     } catch (error) {
-      Logging.instance().log(`Failed to read file: ${file}. Error: ${error}`);
+      Logging.instance().log(
+        `Failed to read file: ${file}. Error: ${error}`,
+        LogLevel.ERROR,
+      );
       return null;
     }
 
diff --git a/electron/helpers/dependencies.ts b/electron/helpers/dependencies.ts
index 87f0728..a9f3694 100644
--- a/electron/helpers/dependencies.ts
+++ b/electron/helpers/dependencies.ts
@@ -1,4 +1,7 @@
-import { LogLevel, Logging } from "../utils/logging";
+import fs, { createWriteStream } from "node:fs";
+import path from "node:path";
+import { pipeline } from "node:stream";
+import { promisify } from "node:util";
 import {
   addHours,
   formatDistanceToNow,
@@ -7,6 +10,10 @@ import {
   intervalToDuration,
   isBefore,
 } from "date-fns";
+import fetch from "node-fetch";
+import unzpier from "unzipper";
+import { z } from "zod";
+
 import {
   exec,
   getArch,
@@ -15,15 +22,8 @@ import {
   getResourcesFolderPath,
   parseJSONObject,
 } from "../utils";
-import fs, { createWriteStream } from "node:fs";
-
+import { Logging, LogLevel } from "../utils/logging";
 import { ConfigFile } from "./config-file";
-import fetch from "node-fetch";
-import path from "node:path";
-import { pipeline } from "node:stream";
-import { promisify } from "node:util";
-import unzpier from "unzipper";
-import { z } from "zod";
 
 const streamPipeline = promisify(pipeline);
 
@@ -164,7 +164,7 @@ export abstract class Dependencies {
 
     const [output, err] = await exec(cli, "--version");
     if (err) {
-      Logging.instance().log(`Error 1: ${err}`, LogLevel.ERROR);
+      Logging.instance().log(`Error: ${err}`, LogLevel.ERROR, true);
     }
 
     // disable updating wakatime-cli when it was built from source
@@ -240,6 +240,7 @@ export abstract class Dependencies {
         Logging.instance().log(
           `Failed to remove file: ${cli}. Error: ${error}`,
           LogLevel.ERROR,
+          true,
         );
       }
     }
diff --git a/electron/main.ts b/electron/main.ts
index 1ca8400..7bd85c8 100644
--- a/electron/main.ts
+++ b/electron/main.ts
@@ -201,7 +201,11 @@ function createTray() {
       tray.popUpContextMenu();
       wakatime?.fetchToday();
     } catch (error) {
-      Logging.instance().log(`Tray click error: ${error}`);
+      Logging.instance().log(
+        `Tray click error: ${error}`,
+        LogLevel.ERROR,
+        true,
+      );
     }
   };
   tray.addListener("click", handleClick);
diff --git a/electron/watchers/wakatime.ts b/electron/watchers/wakatime.ts
index 72078b8..8754b58 100644
--- a/electron/watchers/wakatime.ts
+++ b/electron/watchers/wakatime.ts
@@ -185,7 +185,7 @@ export class Wakatime {
     }
 
     const cli = getCLIPath();
-    Logging.instance().log(`Sending heartbeat: ${cli} ${args}`, LogLevel.DEBUG);
+    Logging.instance().log(`Sending heartbeat: ${cli} ${args}`);
 
     try {
       const [output, err] = await exec(cli, ...args);
@@ -193,15 +193,21 @@ export class Wakatime {
         Logging.instance().log(
           `Error sending heartbeat: ${err}`,
           LogLevel.ERROR,
+          true,
         );
       }
       if (output) {
-        Logging.instance().log(output);
+        Logging.instance().log(
+          `Output from wakatime-cli when sending heartbeat: ${output}`,
+          LogLevel.ERROR,
+          true,
+        );
       }
     } catch (error) {
       Logging.instance().log(
-        `Failed to send heartbeat: ${error}`,
+        `Exception when sending heartbeat: ${error}`,
         LogLevel.ERROR,
+        true,
       );
     }
 
@@ -246,6 +252,13 @@ export class Wakatime {
         );
         return;
       }
+      if (output) {
+        Logging.instance().log(
+          `Output from wakatime-cli when fetching code time: ${output}`,
+          LogLevel.ERROR,
+          true,
+        );
+      }
       this.lastCodeTimeText = output;
       this.tray?.setTitle(` ${output}`);
       this.tray?.setToolTip(` ${output}`);
@@ -268,11 +281,11 @@ export class Wakatime {
     autoUpdater.autoRunAppAfterInstall = true;
 
     autoUpdater.on("checking-for-update", () => {
-      Logging.instance().log("Checking for update");
+      Logging.instance().log("Checking for updates");
     });
     autoUpdater.on("update-available", async (res) => {
       Logging.instance().log(
-        `Update available. Version: ${res.version}, Files: ${res.files.map((file) => file.url).join(", ")}`,
+        `New version available. Version: ${res.version}, Files: ${res.files.map((file) => file.url).join(", ")}`,
       );
       if (!this.canPromptToUpdate(res.version)) {
         Logging.instance().log(
@@ -304,7 +317,10 @@ export class Wakatime {
       Logging.instance().log("Update cancelled");
     });
     autoUpdater.on("error", (err) => {
-      Logging.instance().log(`electron-updater error. Error: ${err.message}`);
+      Logging.instance().log(
+        `electron-updater error. Error: ${err.message}`,
+        LogLevel.ERROR,
+      );
     });
   }
 
diff --git a/electron/watchers/watcher.ts b/electron/watchers/watcher.ts
index ad27b46..3c91035 100644
--- a/electron/watchers/watcher.ts
+++ b/electron/watchers/watcher.ts
@@ -51,7 +51,7 @@ export class Watcher {
         isWrite: false,
       });
     } catch (error) {
-      Logging.instance().log((error as Error).message);
+      Logging.instance().log((error as Error).message, LogLevel.ERROR, true);
     }
   };
 
@@ -79,7 +79,6 @@ export class Watcher {
 
         Logging.instance().log(
           `App changed from ${this.activeWindow?.info.name || "nil"} to ${windowInfo.info.name}`,
-          LogLevel.DEBUG,
         );
 
         this.activeWindow = windowInfo;
@@ -91,13 +90,11 @@ export class Watcher {
           if (isMonitored) {
             Logging.instance().log(
               `Monitoring ${windowInfo.info.name}: ${this.activeWindow.info.path}`,
-              LogLevel.DEBUG,
             );
             this.watchKeyboardEvents();
           } else {
             Logging.instance().log(
               `Not monitoring ${windowInfo.info.name}: ${this.activeWindow.info.path}`,
-              LogLevel.DEBUG,
             );
           }
         }