diff --git a/src/configuration/iconfiguration.ts b/src/configuration/iconfiguration.ts
index 1aa1acf6b50..7c419faeaa2 100644
--- a/src/configuration/iconfiguration.ts
+++ b/src/configuration/iconfiguration.ts
@@ -21,6 +21,7 @@ export interface IAutoSwitchInputMethod {
   switchIMCmd: string;
   obtainIMCmd: string;
 }
+
 export interface IDebugConfiguration {
   /**
    * Boolean indicating whether all logs should be suppressed
diff --git a/src/configuration/remapper.ts b/src/configuration/remapper.ts
index e9ef7452c86..96507cb2b44 100644
--- a/src/configuration/remapper.ts
+++ b/src/configuration/remapper.ts
@@ -86,7 +86,7 @@ export class Remapper implements IRemapper {
         ModeName[vimState.currentMode]
       }. keybindings=${this._configKey}.`
     );
-    let remapping: IKeyRemapping | undefined = Remapper.findMatchingRemap(
+    let remapping: IKeyRemapping | undefined = this.findMatchingRemap(
       userDefinedRemappings,
       keys,
       vimState.currentMode
@@ -181,7 +181,7 @@ export class Remapper implements IRemapper {
     }
   }
 
-  protected static findMatchingRemap(
+  protected findMatchingRemap(
     userDefinedRemappings: Map<string, IKeyRemapping>,
     inputtedKeys: string[],
     currentMode: ModeName
@@ -197,6 +197,7 @@ export class Remapper implements IRemapper {
     for (let sliceLength = startingSliceLength; sliceLength >= range[0]; sliceLength--) {
       const keySlice = inputtedKeys.slice(-sliceLength).join('');
 
+      this._logger.verbose(`trying to find matching remap for keySlice=${keySlice}.`);
       if (userDefinedRemappings.has(keySlice)) {
         // In Insert mode, we allow users to precede remapped commands
         // with extraneous keystrokes (eg. "hello world jj")
diff --git a/src/mode/modeHandler.ts b/src/mode/modeHandler.ts
index 41935dfec76..7893b0c6e4b 100644
--- a/src/mode/modeHandler.ts
+++ b/src/mode/modeHandler.ts
@@ -269,25 +269,28 @@ export class ModeHandler implements vscode.Disposable {
     this.vimState.recordedState.commandList.push(key);
 
     try {
-      // Take the count prefix out to perform the correct remapping.
-      const withinTimeout = now - this.vimState.lastKeyPressedTimestamp < configuration.timeout;
-      const isOperatorCombination = this.vimState.recordedState.operator;
+      const isWithinTimeout = now - this.vimState.lastKeyPressedTimestamp < configuration.timeout;
+      if (!isWithinTimeout) {
+        // sufficient time has elapsed since the prior keypress,
+        // only consider the last keypress for remapping
+        this.vimState.recordedState.commandList = [
+          this.vimState.recordedState.commandList[
+            this.vimState.recordedState.commandList.length - 1
+          ],
+        ];
+      }
 
       let handled = false;
+      const isOperatorCombination = this.vimState.recordedState.operator;
 
-      /**
-       * Check that
-       *
-       * 1) We are not already performing a nonrecursive remapping.
-       * 2) We aren't in normal mode performing on an operator
-       *    Note: ciwjj should be remapped if jj -> <Esc> in insert mode
-       *          dd should not remap the second "d", if d -> "_d in normal mode
-       * 3) We haven't timed out of our previous remapping.
-       */
+      // Check for remapped keys if:
+      // 1. We are not currently performing a non-recursive remapping
+      // 2. We are not in normal mode performing on an operator
+      //    Example: ciwjj should be remapped if jj -> <Esc> in insert mode
+      //             dd should not remap the second "d", if d -> "_d in normal mode
       if (
         !this.vimState.isCurrentlyPerformingRemapping &&
-        (!isOperatorCombination || this.vimState.currentMode !== ModeName.Normal) &&
-        (withinTimeout || this.vimState.recordedState.commandList.length === 1)
+        (!isOperatorCombination || this.vimState.currentMode !== ModeName.Normal)
       ) {
         handled = await this._remappers.sendKey(
           this.vimState.recordedState.commandList,
diff --git a/test/configuration/remapper.test.ts b/test/configuration/remapper.test.ts
index 87c2f75bb9d..8945afd6dfd 100644
--- a/test/configuration/remapper.test.ts
+++ b/test/configuration/remapper.test.ts
@@ -22,6 +22,10 @@ suite('Remapper', () => {
       before: ['j', 'j'],
       after: ['<Esc>'],
     },
+    {
+      before: ['<c-e>'],
+      after: ['<Esc>'],
+    },
   ];
   const defaultNormalModeKeyBindings: IKeyRemapping[] = [
     {
@@ -77,7 +81,7 @@ suite('Remapper', () => {
       inputtedKeys: string[],
       currentMode: ModeName
     ) {
-      return TestRemapper.findMatchingRemap(userDefinedRemappings, inputtedKeys, currentMode);
+      return super.findMatchingRemap(userDefinedRemappings, inputtedKeys, currentMode);
     }
 
     public getRemappedKeySequenceLengthRange(
@@ -297,6 +301,43 @@ suite('Remapper', () => {
     assert.equal(vscode.window.visibleTextEditors.length, 0);
   });
 
+  test('<c-e> -> <esc> in insert mode should go to normal mode', async () => {
+    const expectedDocumentContent = 'lorem ipsum';
+
+    // setup
+    await setupWithBindings({
+      insertModeKeyBindings: defaultInsertModeKeyBindings,
+      normalModeKeyBindings: defaultNormalModeKeyBindings,
+      visualModeKeyBindings: defaultVisualModeKeyBindings,
+    });
+
+    let remapper = new Remappers();
+
+    const edit = new vscode.WorkspaceEdit();
+    edit.insert(
+      vscode.window.activeTextEditor!.document.uri,
+      new vscode.Position(0, 0),
+      expectedDocumentContent
+    );
+    vscode.workspace.applyEdit(edit);
+
+    await modeHandler.handleKeyEvent('i');
+    assertEqual(modeHandler.currentMode.name, ModeName.Insert);
+
+    // act
+    let actual = false;
+    try {
+      actual = await remapper.sendKey(['<C-e>'], modeHandler, modeHandler.vimState);
+    } catch (e) {
+      assert.fail(e);
+    }
+
+    // assert
+    assert.equal(actual, true);
+    assertEqual(modeHandler.currentMode.name, ModeName.Normal);
+    assert.equal(vscode.window.activeTextEditor!.document.getText(), expectedDocumentContent);
+  });
+
   test('leader, w -> closeActiveEditor in normal mode through modehandler', async () => {
     // setup
     await setupWithBindings({