diff --git a/extension.ts b/extension.ts
index 3eefa3c6..9760787d 100644
--- a/extension.ts
+++ b/extension.ts
@@ -20,7 +20,7 @@ import { Notation } from './src/configuration/notation';
 import { StatusBar } from './src/statusBar';
 import { taskQueue } from './src/taskQueue';
 import { ModeHandlerMap } from './src/mode/modeHandlerMap';
-import { Logger } from './src/util/logger';
+import logger from './src/util/logger';
 
 let extensionContext: vscode.ExtensionContext;
 
@@ -95,7 +95,6 @@ export async function activate(context: vscode.ExtensionContext) {
   let compositionState = new CompositionState();
 
   extensionContext.subscriptions.push(StatusBar);
-  extensionContext.subscriptions.push(Logger);
 
   // Reload active configurations
   vscode.workspace.onDidChangeConfiguration(() => {
@@ -366,5 +365,5 @@ async function handleActiveEditorChange(): Promise<void> {
 }
 
 process.on('unhandledRejection', function(reason: any, p: any) {
-  Logger.debug(`Unhandled Rejection at: Promise ${p}. Reason: ${reason}.`);
+  logger.error(`Unhandled Rejection at: Promise ${p}. Reason: ${reason}.`);
 });
diff --git a/package-lock.json b/package-lock.json
index c3de0a86..f6a99e31 100644
--- a/package-lock.json
+++ b/package-lock.json
@@ -275,6 +275,14 @@
       "integrity": "sha1-WWZ/QfrdTyDMvCu5a41Pf3jsA2c=",
       "dev": true
     },
+    "async": {
+      "version": "2.6.1",
+      "resolved": "https://registry.npmjs.org/async/-/async-2.6.1.tgz",
+      "integrity": "sha512-fNEiL2+AZt6AlAw/29Cr0UDe4sRAHCpEHh54WMz+Bb7QfNcFw4h3loofyJpLeQs4Yx7yuqu/2dLgM5hKOs6HlQ==",
+      "requires": {
+        "lodash": "^4.17.10"
+      }
+    },
     "asynckit": {
       "version": "0.4.0",
       "resolved": "https://registry.npmjs.org/asynckit/-/asynckit-0.4.0.tgz",
@@ -621,6 +629,22 @@
         "object-visit": "^1.0.0"
       }
     },
+    "color": {
+      "version": "0.8.0",
+      "resolved": "https://registry.npmjs.org/color/-/color-0.8.0.tgz",
+      "integrity": "sha1-iQwHw/1OZJU3Y4kRz2keVFi2/KU=",
+      "requires": {
+        "color-convert": "^0.5.0",
+        "color-string": "^0.3.0"
+      },
+      "dependencies": {
+        "color-convert": {
+          "version": "0.5.3",
+          "resolved": "https://registry.npmjs.org/color-convert/-/color-convert-0.5.3.tgz",
+          "integrity": "sha1-vbbGnOZg+t/+CwAHzER+G59ygr0="
+        }
+      }
+    },
     "color-convert": {
       "version": "1.9.1",
       "resolved": "https://registry.npmjs.org/color-convert/-/color-convert-1.9.1.tgz",
@@ -633,8 +657,15 @@
     "color-name": {
       "version": "1.1.3",
       "resolved": "https://registry.npmjs.org/color-name/-/color-name-1.1.3.tgz",
-      "integrity": "sha1-p9BVi9icQveV3UIyj3QIMcpTvCU=",
-      "dev": true
+      "integrity": "sha1-p9BVi9icQveV3UIyj3QIMcpTvCU="
+    },
+    "color-string": {
+      "version": "0.3.0",
+      "resolved": "https://registry.npmjs.org/color-string/-/color-string-0.3.0.tgz",
+      "integrity": "sha1-J9RvtnAlxcL6JZk7+/V55HhBuZE=",
+      "requires": {
+        "color-name": "^1.0.0"
+      }
     },
     "color-support": {
       "version": "1.1.3",
@@ -642,6 +673,25 @@
       "integrity": "sha512-qiBjkpbMLO/HL68y+lh4q0/O1MZFj2RX6X/KmMa3+gJD3z+WwI1ZzDHysvqHGS3mP6mznPckpXmw1nI9cJjyRg==",
       "dev": true
     },
+    "colornames": {
+      "version": "0.0.2",
+      "resolved": "https://registry.npmjs.org/colornames/-/colornames-0.0.2.tgz",
+      "integrity": "sha1-2BH9bIT1kClJmorEQ2ICk1uSvjE="
+    },
+    "colors": {
+      "version": "1.3.0",
+      "resolved": "https://registry.npmjs.org/colors/-/colors-1.3.0.tgz",
+      "integrity": "sha512-EDpX3a7wHMWFA7PUHWPHNWqOxIIRSJetuwl0AS5Oi/5FMV8kWm69RTlgm00GKjBO1xFHMtBbL49yRtMMdticBw=="
+    },
+    "colorspace": {
+      "version": "1.0.1",
+      "resolved": "https://registry.npmjs.org/colorspace/-/colorspace-1.0.1.tgz",
+      "integrity": "sha1-yZx5btMRKLmHalLh7l7gOkpxl0k=",
+      "requires": {
+        "color": "0.8.x",
+        "text-hex": "0.0.x"
+      }
+    },
     "combined-stream": {
       "version": "1.0.6",
       "resolved": "https://registry.npmjs.org/combined-stream/-/combined-stream-1.0.6.tgz",
@@ -752,15 +802,6 @@
       "integrity": "sha1-QGXiATz5+5Ft39gu+1Bq1MZ2kGI=",
       "dev": true
     },
-    "debug": {
-      "version": "2.6.9",
-      "resolved": "https://registry.npmjs.org/debug/-/debug-2.6.9.tgz",
-      "integrity": "sha512-bC7ElrdJaJnPbAP+1EotYvqZsb3ecl5wi6Bfi6BJTUcNowp6cvspg0jXznRTKDjm/E7AdgFBVeAPVMNcKGsHMA==",
-      "dev": true,
-      "requires": {
-        "ms": "2.0.0"
-      }
-    },
     "debug-fabulous": {
       "version": "1.1.0",
       "resolved": "https://registry.npmjs.org/debug-fabulous/-/debug-fabulous-1.1.0.tgz",
@@ -894,6 +935,16 @@
       "integrity": "sha1-9B8cEL5LAOh7XxPaaAdZ8sW/0+I=",
       "dev": true
     },
+    "diagnostics": {
+      "version": "1.1.0",
+      "resolved": "https://registry.npmjs.org/diagnostics/-/diagnostics-1.1.0.tgz",
+      "integrity": "sha1-4QkJALSVI+hSe+IPCBJ1IF8q42o=",
+      "requires": {
+        "colorspace": "1.0.x",
+        "enabled": "1.0.x",
+        "kuler": "0.0.x"
+      }
+    },
     "diff": {
       "version": "3.5.0",
       "resolved": "https://registry.npmjs.org/diff/-/diff-3.5.0.tgz",
@@ -988,6 +1039,14 @@
         "jsbn": "~0.1.0"
       }
     },
+    "enabled": {
+      "version": "1.0.2",
+      "resolved": "https://registry.npmjs.org/enabled/-/enabled-1.0.2.tgz",
+      "integrity": "sha1-ll9lE9LC0cX0ZStkouM5ZGf8L5M=",
+      "requires": {
+        "env-variable": "0.0.x"
+      }
+    },
     "end-of-stream": {
       "version": "0.1.5",
       "resolved": "https://registry.npmjs.org/end-of-stream/-/end-of-stream-0.1.5.tgz",
@@ -997,6 +1056,11 @@
         "once": "~1.3.0"
       }
     },
+    "env-variable": {
+      "version": "0.0.4",
+      "resolved": "https://registry.npmjs.org/env-variable/-/env-variable-0.0.4.tgz",
+      "integrity": "sha512-+jpGxSWG4vr6gVxUHOc4p+ilPnql7NzZxOZBxNldsKGjCF+97df3CbuX7XMaDa5oAVkKQj4rKp38rYdC4VcpDg=="
+    },
     "error-ex": {
       "version": "1.3.1",
       "resolved": "https://registry.npmjs.org/error-ex/-/error-ex-1.3.1.tgz",
@@ -1122,6 +1186,15 @@
         "to-regex": "^3.0.1"
       },
       "dependencies": {
+        "debug": {
+          "version": "2.6.9",
+          "resolved": "https://registry.npmjs.org/debug/-/debug-2.6.9.tgz",
+          "integrity": "sha512-bC7ElrdJaJnPbAP+1EotYvqZsb3ecl5wi6Bfi6BJTUcNowp6cvspg0jXznRTKDjm/E7AdgFBVeAPVMNcKGsHMA==",
+          "dev": true,
+          "requires": {
+            "ms": "2.0.0"
+          }
+        },
         "define-property": {
           "version": "0.2.5",
           "resolved": "https://registry.npmjs.org/define-property/-/define-property-0.2.5.tgz",
@@ -1332,6 +1405,11 @@
         "pend": "~1.2.0"
       }
     },
+    "fecha": {
+      "version": "2.3.3",
+      "resolved": "https://registry.npmjs.org/fecha/-/fecha-2.3.3.tgz",
+      "integrity": "sha512-lUGBnIamTAwk4znq5BcqsDaxSmZ9nDVJaij6NvRt/Tg4R69gERA+otPKbS86ROw9nxVMw2/mp1fnaiWqbs6Sdg=="
+    },
     "filename-regex": {
       "version": "2.0.1",
       "resolved": "https://registry.npmjs.org/filename-regex/-/filename-regex-2.0.1.tgz",
@@ -3535,6 +3613,14 @@
       "integrity": "sha512-s5kLOcnH0XqDO+FvuaLX8DDjZ18CGFk7VygH40QoKPUQhW4e2rvM0rwUq0t8IQDOwYSeLK01U90OjzBTme2QqA==",
       "dev": true
     },
+    "kuler": {
+      "version": "0.0.0",
+      "resolved": "https://registry.npmjs.org/kuler/-/kuler-0.0.0.tgz",
+      "integrity": "sha1-tmu0a5NOVQ9Z2BiEjgq7pPf1VTw=",
+      "requires": {
+        "colornames": "0.0.2"
+      }
+    },
     "lazystream": {
       "version": "1.0.0",
       "resolved": "https://registry.npmjs.org/lazystream/-/lazystream-1.0.0.tgz",
@@ -3729,6 +3815,24 @@
         "lodash.escape": "^3.0.0"
       }
     },
+    "logform": {
+      "version": "1.7.0",
+      "resolved": "https://registry.npmjs.org/logform/-/logform-1.7.0.tgz",
+      "integrity": "sha512-IyyAkQiA0I3LEar69J0bR5kg7204883jsWW4os9ypXiEsHueuPwfEClC3aSelhG+pIbMD0l23nAkz5VRXZYMWA==",
+      "requires": {
+        "colors": "^1.2.1",
+        "fecha": "^2.3.3",
+        "ms": "^2.1.1",
+        "triple-beam": "^1.2.0"
+      },
+      "dependencies": {
+        "ms": {
+          "version": "2.1.1",
+          "resolved": "https://registry.npmjs.org/ms/-/ms-2.1.1.tgz",
+          "integrity": "sha512-tgp+dl5cGk28utYktBsrFqA7HKgrhgPsg6Z/EfhWI4gl1Hwq8B/GmY/0oXZ6nF8hDVesS/FpnYaD/kOWhYQvyg=="
+        }
+      }
+    },
     "loud-rejection": {
       "version": "1.6.0",
       "resolved": "https://registry.npmjs.org/loud-rejection/-/loud-rejection-1.6.0.tgz",
@@ -4296,6 +4400,11 @@
         "wrappy": "1"
       }
     },
+    "one-time": {
+      "version": "0.0.4",
+      "resolved": "https://registry.npmjs.org/one-time/-/one-time-0.0.4.tgz",
+      "integrity": "sha1-+M33eISCb+Tf+T46nMN7HkSAdC4="
+    },
     "orchestrator": {
       "version": "0.3.8",
       "resolved": "https://registry.npmjs.org/orchestrator/-/orchestrator-0.3.8.tgz",
@@ -5037,6 +5146,15 @@
         "use": "^3.1.0"
       },
       "dependencies": {
+        "debug": {
+          "version": "2.6.9",
+          "resolved": "https://registry.npmjs.org/debug/-/debug-2.6.9.tgz",
+          "integrity": "sha512-bC7ElrdJaJnPbAP+1EotYvqZsb3ecl5wi6Bfi6BJTUcNowp6cvspg0jXznRTKDjm/E7AdgFBVeAPVMNcKGsHMA==",
+          "dev": true,
+          "requires": {
+            "ms": "2.0.0"
+          }
+        },
         "define-property": {
           "version": "0.2.5",
           "resolved": "https://registry.npmjs.org/define-property/-/define-property-0.2.5.tgz",
@@ -5249,6 +5367,11 @@
         "tweetnacl": "~0.14.0"
       }
     },
+    "stack-trace": {
+      "version": "0.0.10",
+      "resolved": "https://registry.npmjs.org/stack-trace/-/stack-trace-0.0.10.tgz",
+      "integrity": "sha1-VHxws0fo0ytOEI6hoqFZ5f3eGcA="
+    },
     "stat-mode": {
       "version": "0.2.2",
       "resolved": "https://registry.npmjs.org/stat-mode/-/stat-mode-0.2.2.tgz",
@@ -5406,6 +5529,11 @@
         "inherits": "2"
       }
     },
+    "text-hex": {
+      "version": "0.0.0",
+      "resolved": "https://registry.npmjs.org/text-hex/-/text-hex-0.0.0.tgz",
+      "integrity": "sha1-V4+8haapJjbkLdF7QdAhjM6esrM="
+    },
     "through": {
       "version": "2.3.8",
       "resolved": "https://registry.npmjs.org/through/-/through-2.3.8.tgz",
@@ -5538,6 +5666,11 @@
       "integrity": "sha1-WIeWa7WCpFA6QetST301ARgVphM=",
       "dev": true
     },
+    "triple-beam": {
+      "version": "1.3.0",
+      "resolved": "https://registry.npmjs.org/triple-beam/-/triple-beam-1.3.0.tgz",
+      "integrity": "sha512-XrHUvV5HpdLmIj4uVMxHggLbFSZYIn7HEWsqePZcI50pco+MPqJ50wMGY794X7AOOhxOBAjbkqfAbEe/QMp2Lw=="
+    },
     "tslib": {
       "version": "1.9.1",
       "resolved": "https://registry.npmjs.org/tslib/-/tslib-1.9.1.tgz",
@@ -6114,6 +6247,37 @@
         "isexe": "^2.0.0"
       }
     },
+    "winston": {
+      "version": "3.0.0-rc6",
+      "resolved": "https://registry.npmjs.org/winston/-/winston-3.0.0-rc6.tgz",
+      "integrity": "sha512-4QwLccPbU/aJMA+j6uYTQ8TobwLKPWhpceJZwz1lkQ+wYv7bxGyAHIdbfEOrxsKHD8zRCcgCXPbbpV3BDRD1rw==",
+      "requires": {
+        "async": "^2.6.0",
+        "diagnostics": "^1.0.1",
+        "is-stream": "^1.1.0",
+        "logform": "^1.7.0",
+        "one-time": "0.0.4",
+        "stack-trace": "0.0.x",
+        "triple-beam": "^1.3.0",
+        "winston-transport": "^4.0.0"
+      }
+    },
+    "winston-console-for-electron": {
+      "version": "0.0.3",
+      "resolved": "https://registry.npmjs.org/winston-console-for-electron/-/winston-console-for-electron-0.0.3.tgz",
+      "integrity": "sha512-wwAdjWYgqsqJiMxir1LMfySFKOn8EJ7rgoA2EBxHnMZ5Dw6i6FV/ZfeNzzceDej6E4Zx9Iw35Fjr1g/rMkVQMQ==",
+      "requires": {
+        "winston-transport": "4.1.0"
+      }
+    },
+    "winston-transport": {
+      "version": "4.1.0",
+      "resolved": "https://registry.npmjs.org/winston-transport/-/winston-transport-4.1.0.tgz",
+      "integrity": "sha512-rNMfXfGfTyiOrAJ9KLLy0nlow98NyD0oNCOSnP3jnNVHoKsJGLDsa8BaOH+ftKDR5pZKJMBhbQNEft7Vr+dJLw==",
+      "requires": {
+        "triple-beam": "^1.2.0"
+      }
+    },
     "wrappy": {
       "version": "1.0.2",
       "resolved": "https://registry.npmjs.org/wrappy/-/wrappy-1.0.2.tgz",
diff --git a/package.json b/package.json
index 9978b26a..affc934f 100644
--- a/package.json
+++ b/package.json
@@ -340,6 +340,13 @@
       "title": "Vim Configuration",
       "type": "object",
       "properties": {
+        "vim.debug": {
+          "type": "object",
+          "description": "Extension debugging options",
+          "default": {
+            "loggingLevel": "error"
+          }
+        },
         "vim.otherModesKeyBindings": {
           "type": "array",
           "description": "Remapped keys in normal mode. Allows mapping to vim commands or vscode actions. See README for more."
@@ -587,7 +594,9 @@
     "lodash": "4.17.10",
     "neovim-client": "2.1.0",
     "promised-neovim-client": "2.0.2",
-    "untildify": "3.0.3"
+    "untildify": "3.0.3",
+    "winston": "^3.0.0-rc6",
+    "winston-console-for-electron": "0.0.3"
   },
   "devDependencies": {
     "@types/clipboardy": "1.1.0",
diff --git a/src/cmd_line/commandLine.ts b/src/cmd_line/commandLine.ts
index 4506d43a..989e9d0f 100644
--- a/src/cmd_line/commandLine.ts
+++ b/src/cmd_line/commandLine.ts
@@ -1,13 +1,12 @@
 import * as vscode from 'vscode';
 
 import { configuration } from '../configuration/configuration';
-import { Neovim } from '../neovim/neovim';
+import logger from '../util/logger';
 import { VimState } from '../state/vimState';
 import { StatusBar } from '../statusBar';
 import * as parser from './parser';
 import * as util from '../util';
 import { VimError, ErrorCode } from '../error';
-import { Logger } from '../util/logger';
 import { CommandLineHistory } from './commandLineHistory';
 
 export class CommandLine {
@@ -15,7 +14,7 @@ export class CommandLine {
 
   public static async PromptAndRun(initialText: string, vimState: VimState): Promise<void> {
     if (!vscode.window.activeTextEditor) {
-      Logger.debug('CommandLine: No active document');
+      logger.debug('CommandLine: No active document');
       return;
     }
 
@@ -79,7 +78,7 @@ export class CommandLine {
     vimState: VimState
   ): Promise<string | undefined> {
     if (!vscode.window.activeTextEditor) {
-      Logger.debug('CommandLine: No active document.');
+      logger.debug('CommandLine: No active document.');
       return '';
     }
 
diff --git a/src/cmd_line/commandLineHistory.ts b/src/cmd_line/commandLineHistory.ts
index 6f202863..5355d466 100644
--- a/src/cmd_line/commandLineHistory.ts
+++ b/src/cmd_line/commandLineHistory.ts
@@ -1,7 +1,7 @@
 import * as vscode from 'vscode';
 
 import { configuration } from '../configuration/configuration';
-import { Logger } from '../util/logger';
+import logger from '../util/logger';
 
 export class CommandLineHistory {
   private _history: string[] = [];
@@ -49,14 +49,14 @@ export class CommandLineHistory {
 
         if (err) {
           if (err.code === 'ENOENT') {
-            Logger.debug('CommandLineHistory: History does not exist.');
+            logger.debug('CommandLineHistory: History does not exist.');
             // add ccommands that were run before history was loaded.
             if (this._history.length > 0) {
               this.save();
             }
             resolve();
           } else {
-            Logger.error(err.message, 'Failed to load history.');
+            logger.error(`Failed to load history. err=${err.message}.`);
             reject();
           }
           return;
@@ -77,14 +77,14 @@ export class CommandLineHistory {
             }
             resolve();
           } else {
-            Logger.error(
+            logger.error(
               'CommandLineHistory: The history format is unknown.',
               'Failed to load history.'
             );
             reject();
           }
         } catch (e) {
-          Logger.error(e.message, 'Failed to load history.');
+          logger.error(e.message, 'Failed to load history.');
           reject();
         }
       });
@@ -94,7 +94,7 @@ export class CommandLineHistory {
   public async save(): Promise<void> {
     return new Promise<void>((resolve, reject) => {
       if (this._is_loading) {
-        Logger.debug('CommandLineHistory: Failed to save history because history is loading.');
+        logger.debug('CommandLineHistory: Failed to save history because history is loading.');
         resolve();
         return;
       }
@@ -105,7 +105,7 @@ export class CommandLineHistory {
         if (!err) {
           resolve();
         } else {
-          Logger.error(err.message, 'Failed to save history.');
+          logger.error(err.message, 'Failed to save history.');
           reject();
         }
       });
diff --git a/src/configuration/configuration.ts b/src/configuration/configuration.ts
index 6477bd8b..b2b04a68 100644
--- a/src/configuration/configuration.ts
+++ b/src/configuration/configuration.ts
@@ -3,7 +3,12 @@ import * as vscode from 'vscode';
 import { Globals } from '../globals';
 import { taskQueue } from '../taskQueue';
 import { Notation } from './notation';
-import { IConfiguration, IKeyRemapping, IModeSpecificStrings } from './iconfiguration';
+import {
+  IConfiguration,
+  IKeyRemapping,
+  IModeSpecificStrings,
+  IDebugConfiguration,
+} from './iconfiguration';
 
 const packagejson: {
   contributes: {
@@ -230,6 +235,10 @@ class Configuration implements IConfiguration {
     replace: '#000000',
   };
 
+  debug: IDebugConfiguration = {
+    loggingLevel: 'error',
+  };
+
   searchHighlightColor = 'rgba(150, 150, 255, 0.3)';
 
   @overlapSetting({ codeName: 'tabSize', default: 8 })
@@ -368,4 +377,4 @@ function overlapSetting(args: {
   };
 }
 
-export let configuration = new Configuration();
+export const configuration = new Configuration();
diff --git a/src/configuration/iconfiguration.ts b/src/configuration/iconfiguration.ts
index 270745c3..d3736030 100644
--- a/src/configuration/iconfiguration.ts
+++ b/src/configuration/iconfiguration.ts
@@ -15,6 +15,14 @@ export interface IKeyRemapping {
   commands?: { command: string; args: any[] }[];
 }
 
+export interface IDebugConfiguration {
+  /**
+   * Maximum level of messages to log.
+   * Supported values: ['error', 'warn', 'info', 'verbose', 'debug', 'silly']
+   */
+  loggingLevel: string;
+}
+
 export interface IConfiguration {
   /**
    * Use the system's clipboard when copying.
@@ -131,6 +139,11 @@ export interface IConfiguration {
    */
   statusBarColors: IModeSpecificStrings<string>;
 
+  /**
+   * Extension debugging settings
+   */
+  debug: IDebugConfiguration;
+
   /**
    * Color of search highlights.
    */
diff --git a/src/history/historyTracker.ts b/src/history/historyTracker.ts
index e30b191b..bb8180b2 100644
--- a/src/history/historyTracker.ts
+++ b/src/history/historyTracker.ts
@@ -17,7 +17,7 @@ import { Position } from './../common/motion/position';
 import { RecordedState } from './../state/recordedState';
 import { VimState } from './../state/vimState';
 import { TextEditor } from './../textEditor';
-import { Logger } from './../util/logger';
+import logger from './../util/logger';
 
 const diffEngine = new DiffMatchPatch.diff_match_patch();
 diffEngine.Diff_Timeout = 1; // 1 second
@@ -184,7 +184,7 @@ export class HistoryTracker {
   private get currentHistoryStep(): HistoryStep {
     if (this.currentHistoryStepIndex === -1) {
       let msg = 'HistoryTracker: Tried to modify history at index -1';
-      Logger.debug(msg);
+      logger.debug(msg);
       throw new Error(msg);
     }
 
@@ -455,7 +455,7 @@ export class HistoryTracker {
    */
   async undoAndRemoveChanges(n: number): Promise<void> {
     if (this.currentHistoryStep.changes.length < n) {
-      Logger.debug('HistoryTracker: Something bad happened in removeChange');
+      logger.debug('HistoryTracker: Something bad happened in removeChange');
       return;
     }
 
diff --git a/src/mode/modeHandler.ts b/src/mode/modeHandler.ts
index 81f5c689..dc8a99e0 100644
--- a/src/mode/modeHandler.ts
+++ b/src/mode/modeHandler.ts
@@ -30,7 +30,7 @@ import {
   TextTransformations,
 } from './../transformations/transformations';
 import { Mode, ModeName, VSCodeVimCursorType } from './mode';
-import { Logger } from '../util/logger';
+import logger from '../util/logger';
 
 export class ModeHandler implements vscode.Disposable {
   private _disposables: vscode.Disposable[] = [];
@@ -865,7 +865,7 @@ export class ModeHandler implements vscode.Disposable {
 
     if (textTransformations.length > 0) {
       if (areAnyTransformationsOverlapping(textTransformations)) {
-        Logger.debug(
+        logger.debug(
           `Text transformations are overlapping. Falling back to serial
            transformations. This is generally a very bad sign. Try to make
            your text transformations operate on non-overlapping ranges.`
@@ -1370,7 +1370,7 @@ export class ModeHandler implements vscode.Disposable {
       }
     }
 
-    let text = [];
+    let text: string[] = [];
 
     if (configuration.showmodename) {
       text.push(this.currentMode.getStatusBarText(this.vimState));
diff --git a/src/neovim/neovim.ts b/src/neovim/neovim.ts
index a4757901..873b8148 100644
--- a/src/neovim/neovim.ts
+++ b/src/neovim/neovim.ts
@@ -5,12 +5,11 @@ import { attach, Nvim } from 'promised-neovim-client';
 import * as vscode from 'vscode';
 
 import { configuration } from '../configuration/configuration';
-import { ModeName } from '../mode/mode';
 import { Register, RegisterMode } from '../register/register';
 import { TextEditor } from '../textEditor';
 import { Position } from './../common/motion/position';
 import { VimState } from './../state/vimState';
-import { Logger } from '../util/logger';
+import logger from '../util/logger';
 
 export class Neovim implements vscode.Disposable {
   private process: ChildProcess;
@@ -25,7 +24,7 @@ export class Neovim implements vscode.Disposable {
       cwd: dir,
     });
     this.process.on('error', err => {
-      Logger.error(err.message, `Neovim: Error spawning neovim. Error=${err.message}.`);
+      logger.error(err.message, `Neovim: Error spawning neovim. Error=${err.message}.`);
       configuration.enableNeovim = false;
     });
     this.nvim = await attach(this.process.stdin, this.process.stdout);
@@ -115,7 +114,7 @@ export class Neovim implements vscode.Disposable {
       fixedLines.join('\n')
     );
 
-    Logger.debug(
+    logger.debug(
       `Neovim: ${lines.length} lines in nvim but ${TextEditor.getLineCount()} in editor.`
     );
 
diff --git a/src/state/recordedState.ts b/src/state/recordedState.ts
index 28be288f..ccec9c29 100644
--- a/src/state/recordedState.ts
+++ b/src/state/recordedState.ts
@@ -69,7 +69,7 @@ export class RecordedState {
    */
   public getCurrentCommandWithoutCountPrefix(): string[] {
     const commandList = this.commandList;
-    const result = [];
+    const result: string[] = [];
     let previousWasCount = true;
 
     for (const commandKey of commandList) {
diff --git a/src/state/searchState.ts b/src/state/searchState.ts
index 79355a00..472a9dcd 100644
--- a/src/state/searchState.ts
+++ b/src/state/searchState.ts
@@ -1,6 +1,6 @@
 import * as vscode from 'vscode';
 
-import { configuration } from '../../src/configuration/configuration';
+import { configuration } from '../configuration/configuration';
 import { Position } from './../common/motion/position';
 import { ModeName } from './../mode/mode';
 import { TextEditor } from './../textEditor';
@@ -111,7 +111,7 @@ export class SearchState {
       const finalPos = new Position(TextEditor.getLineCount() - 1, 0).getLineEndIncludingEOL();
       const text = TextEditor.getText(new vscode.Range(new Position(0, 0), finalPos));
       const lineLengths = text.split('\n').map(x => x.length + 1);
-      let sumLineLengths = [];
+      let sumLineLengths: number[] = [];
       let curLength = 0;
       for (const length of lineLengths) {
         sumLineLengths.push(curLength);
diff --git a/src/state/vimState.ts b/src/state/vimState.ts
index fefa330f..cc265a71 100644
--- a/src/state/vimState.ts
+++ b/src/state/vimState.ts
@@ -1,4 +1,3 @@
-import { Nvim } from 'promised-neovim-client';
 import * as vscode from 'vscode';
 
 import { ModeName } from '../mode/mode';
@@ -13,7 +12,7 @@ import { GlobalState } from './../state/globalState';
 import { ReplaceState } from './../state/replaceState';
 import { RecordedState } from './recordedState';
 import { Neovim } from '../neovim/neovim';
-import { Logger } from '../util/logger';
+import logger from '../util/logger';
 
 /**
  * The VimState class holds permanent state that carries over from action
@@ -147,7 +146,7 @@ export class VimState implements vscode.Disposable {
   public set allCursors(value: Range[]) {
     for (const cursor of value) {
       if (!cursor.start.isValid() || !cursor.stop.isValid()) {
-        Logger.debug('VimState: invalid value for set cursor position. This is probably bad?');
+        logger.debug('VimState: invalid value for set cursor position. This is probably bad?');
       }
     }
 
diff --git a/src/statusBar.ts b/src/statusBar.ts
index cfad38b4..aaa6f179 100644
--- a/src/statusBar.ts
+++ b/src/statusBar.ts
@@ -1,5 +1,4 @@
 import * as vscode from 'vscode';
-
 import { ModeName } from './mode/mode';
 
 class StatusBarImpl implements vscode.Disposable {
@@ -57,4 +56,4 @@ class StatusBarImpl implements vscode.Disposable {
   }
 }
 
-export let StatusBar = new StatusBarImpl();
+export const StatusBar = new StatusBarImpl();
diff --git a/src/util.ts b/src/util.ts
index bd54c73b..9e0e95e5 100644
--- a/src/util.ts
+++ b/src/util.ts
@@ -3,7 +3,7 @@ import * as vscode from 'vscode';
 
 import { Position } from './common/motion/position';
 import { Range } from './common/motion/range';
-import { Logger } from './util/logger';
+import logger from './util/logger';
 
 export async function showInfo(message: string): Promise<{}> {
   return vscode.window.showInformationMessage('Vim: ' + message) as {};
@@ -20,7 +20,7 @@ export class Clipboard {
     try {
       clipboardy.writeSync(text);
     } catch (e) {
-      Logger.error(e, `Clipboard: Error copying to clipboard. Error=${e}`);
+      logger.error(e, `Clipboard: Error copying to clipboard. Error=${e}`);
     }
   }
 
@@ -85,7 +85,7 @@ export async function getExternalExtensionDirPath(): Promise<string> {
       if (!err || err.code === 'EEXIST') {
         resolve(extensionFolder);
       } else {
-        Logger.debug(err.message);
+        logger.error(err.message);
         reject(err);
       }
     });
diff --git a/src/util/logger.ts b/src/util/logger.ts
index e00c795c..9e86f053 100644
--- a/src/util/logger.ts
+++ b/src/util/logger.ts
@@ -1,64 +1,11 @@
-import * as vscode from 'vscode';
+import { configuration } from '../configuration/configuration';
+import * as winston from 'winston';
+import { ConsoleForElectron } from 'winston-console-for-electron';
 
-enum LoggingLevel {
-  Error = 0,
-  Warn = 1,
-  Debug = 2,
-}
+const logger = winston.createLogger({
+  level: configuration.debug.loggingLevel,
+  format: winston.format.simple(),
+  transports: [new ConsoleForElectron()],
+});
 
-class LoggerImpl implements vscode.Disposable {
-  private _channel: vscode.OutputChannel;
-
-  constructor() {
-    this._channel = vscode.window.createOutputChannel('vscodevim');
-  }
-
-  public debug(message?: string): void {
-    this.emitMessage(LoggingLevel.Debug, message);
-  }
-
-  public error(message?: string, friendlyMessage?: string): void {
-    this.emitMessage(LoggingLevel.Error, message);
-    vscode.window.showErrorMessage(`Error: ${friendlyMessage} || ${message}`);
-  }
-
-  private emitMessage(loggingLevel: LoggingLevel, message?: string) {
-    if (message === undefined) {
-      return;
-    }
-
-    message = `${LoggerImpl.getNow()} - ${message}`;
-
-    this._channel.appendLine(message);
-
-    switch (loggingLevel) {
-      case LoggingLevel.Error:
-        console.error(message);
-        break;
-      case LoggingLevel.Warn:
-        console.warn(message);
-        break;
-      case LoggingLevel.Debug:
-        console.log(message);
-        break;
-    }
-  }
-
-  private static getNow(): string {
-    const now = new Date();
-    let time = [String(now.getHours()), String(now.getMinutes()), String(now.getSeconds())];
-    for (let i = 0; i < time.length; i++) {
-      if (Number(time[i]) < 10) {
-        time[i] = '0' + time[i];
-      }
-    }
-
-    return time.join(':');
-  }
-
-  dispose() {
-    this._channel.dispose();
-  }
-}
-
-export let Logger = new LoggerImpl();
+export default logger;
diff --git a/test/testConfiguration.ts b/test/testConfiguration.ts
index 3b1f2087..4e65f69b 100644
--- a/test/testConfiguration.ts
+++ b/test/testConfiguration.ts
@@ -40,6 +40,9 @@ export class Configuration implements IConfiguration {
     visualblock: '#86592d';
     replace: '#000000';
   };
+  debug: {
+    loggingLevel: 'info';
+  };
   searchHighlightColor = 'rgba(150, 150, 255, 0.3)';
   tabstop = 2;
   userCursor = vscode.TextEditorCursorStyle.Line;
diff --git a/tsconfig.json b/tsconfig.json
index 324bc4d6..4d7b879f 100644
--- a/tsconfig.json
+++ b/tsconfig.json
@@ -3,7 +3,6 @@
     "module": "commonjs",
     "target": "es6",
     "outDir": "out",
-    "noImplicitAny": true,
     "noImplicitReturns": true,
     "noUnusedLocals": false,
     "noUnusedParameters": false,