diff --git a/examples/api-tests/src/keybindings.spec.js b/examples/api-tests/src/keybindings.spec.js
index 2087a697cfa15..5f862ee5cb3a9 100644
--- a/examples/api-tests/src/keybindings.spec.js
+++ b/examples/api-tests/src/keybindings.spec.js
@@ -93,7 +93,7 @@ describe('Keybindings', function () {
         assert.notEqual(executedCommand, id);
     });
 
-    it('later registered keybinding should has higher priority', async () => {
+    it('later registered keybinding should have higher priority', async () => {
         const id = '__test:keybindings.copy';
         toTearDown.push(commands.registerCommand({ id }, {
             execute: () => { }
diff --git a/packages/core/src/browser/keybinding.ts b/packages/core/src/browser/keybinding.ts
index 06b22cca8362f..394841590f893 100644
--- a/packages/core/src/browser/keybinding.ts
+++ b/packages/core/src/browser/keybinding.ts
@@ -232,7 +232,7 @@ export class KeybindingRegistry {
         try {
             this.resolveKeybinding(binding);
             const scoped = Object.assign(binding, { scope });
-            this.keymaps[scope].unshift(scoped);
+            this.insertBindingIntoScope(scoped, scope);
             return Disposable.create(() => {
                 const index = this.keymaps[scope].indexOf(scoped);
                 if (index !== -1) {
@@ -245,6 +245,22 @@ export class KeybindingRegistry {
         }
     }
 
+    /**
+     * Ensures that keybindings are inserted in order of increasing length of binding to ensure that if a
+     * user triggers a short keybinding (e.g. ctrl+k), the UI won't wait for a longer one (e.g. ctrl+k enter)
+     */
+    protected insertBindingIntoScope(item: common.Keybinding & { scope: KeybindingScope; }, scope: KeybindingScope): void {
+        const scopedKeymap = this.keymaps[scope];
+        const getNumberOfKeystrokes = (binding: common.Keybinding): number => (binding.keybinding.trim().match(/\s/)?.length ?? 0) + 1;
+        const numberOfKeystrokesInBinding = getNumberOfKeystrokes(item);
+        const indexOfFirstItemWithEqualStrokes = scopedKeymap.findIndex(existingBinding => getNumberOfKeystrokes(existingBinding) === numberOfKeystrokesInBinding);
+        if (indexOfFirstItemWithEqualStrokes > -1) {
+            scopedKeymap.splice(indexOfFirstItemWithEqualStrokes, 0, item);
+        } else {
+            scopedKeymap.push(item);
+        }
+    }
+
     /**
      * Ensure that the `resolved` property of the given binding is set by calling the KeyboardLayoutService.
      */
diff --git a/packages/editor-preview/src/browser/editor-preview-contribution.ts b/packages/editor-preview/src/browser/editor-preview-contribution.ts
index 0895e9e88ab6b..b5b870b7995f4 100644
--- a/packages/editor-preview/src/browser/editor-preview-contribution.ts
+++ b/packages/editor-preview/src/browser/editor-preview-contribution.ts
@@ -21,7 +21,7 @@ import { EditorPreviewWidget } from './editor-preview-widget';
 
 export namespace EditorPreviewCommands {
     export const PIN_PREVIEW_COMMAND: Command = {
-        id: 'editor-preview-pin-editor',
+        id: 'workbench.action.keepEditor',
         label: 'Keep Open'
     };
 }
diff --git a/packages/plugin-ext-vscode/src/browser/plugin-vscode-commands-contribution.ts b/packages/plugin-ext-vscode/src/browser/plugin-vscode-commands-contribution.ts
index c471856b1906f..7b5ad6809ecfa 100755
--- a/packages/plugin-ext-vscode/src/browser/plugin-vscode-commands-contribution.ts
+++ b/packages/plugin-ext-vscode/src/browser/plugin-vscode-commands-contribution.ts
@@ -418,7 +418,6 @@ export class PluginVscodeCommandsContribution implements CommandContribution {
 
         /**
          * TODO:
-         * Keep Open: workbench.action.keepEditor
          * Open Next: workbench.action.openNextRecentlyUsedEditorInGroup
          * Open Previous: workbench.action.openPreviousRecentlyUsedEditorInGroup
          * Copy Path of Active File: workbench.action.files.copyPathOfActiveFile