diff --git a/package.json b/package.json
index 7e0c041002..c32fdc4699 100644
--- a/package.json
+++ b/package.json
@@ -42,6 +42,7 @@
     "onCommand:PowerShell.OpenExamplesFolder",
     "onCommand:PowerShell.EnableISEMode",
     "onCommand:PowerShell.DisableISEMode",
+    "onCommand:PowerShell.ToggleISEMode",
     "onView:PowerShellCommands"
   ],
   "dependencies": {
@@ -155,6 +156,11 @@
         "title": "Disable ISE Mode (restore to defaults)",
         "category": "PowerShell"
       },
+      {
+        "command": "PowerShell.ToggleISEMode",
+        "title": "Toggle ISE Mode",
+        "category": "PowerShell"
+      },
       {
         "command": "PowerShell.RefreshCommandsExplorer",
         "title": "Refresh Command Explorer",
diff --git a/src/features/ISECompatibility.ts b/src/features/ISECompatibility.ts
index d8abfa92b4..eb377a7c0c 100644
--- a/src/features/ISECompatibility.ts
+++ b/src/features/ISECompatibility.ts
@@ -25,22 +25,29 @@ export class ISECompatibilityFeature implements vscode.Disposable {
         { path: "editor", name: "wordSeparators", value: "`~!@#%^&*()-=+[{]}\\|;:'\",.<>/?" },
         { path: "powershell.buttons", name: "showPanelMovementButtons", value: true }
     ];
-    private iseCommandRegistration: vscode.Disposable;
-    private defaultCommandRegistration: vscode.Disposable;
+
+    private _commandRegistrations: vscode.Disposable[] = [];
+    private _iseModeEnabled: boolean;
 
     constructor() {
-        this.iseCommandRegistration = vscode.commands.registerCommand(
-            "PowerShell.EnableISEMode", this.EnableISEMode);
-        this.defaultCommandRegistration = vscode.commands.registerCommand(
-            "PowerShell.DisableISEMode", this.DisableISEMode);
+        // TODO: This test isn't great.
+        const testSetting = ISECompatibilityFeature.settings[ISECompatibilityFeature.settings.length - 1];
+        this._iseModeEnabled = vscode.workspace.getConfiguration(testSetting.path).get(testSetting.name) === testSetting.value;
+        this._commandRegistrations = [
+            vscode.commands.registerCommand("PowerShell.EnableISEMode", async () => { await this.EnableISEMode(); }),
+            vscode.commands.registerCommand("PowerShell.DisableISEMode", async () => { await this.DisableISEMode(); }),
+            vscode.commands.registerCommand("PowerShell.ToggleISEMode", async () => { await this.ToggleISEMode(); })
+        ]
     }
 
     public dispose() {
-        this.iseCommandRegistration.dispose();
-        this.defaultCommandRegistration.dispose();
+        for (const command of this._commandRegistrations) {
+            command.dispose();
+        }
     }
 
     private async EnableISEMode() {
+        this._iseModeEnabled = true;
         for (const iseSetting of ISECompatibilityFeature.settings) {
             try {
                 await vscode.workspace.getConfiguration(iseSetting.path).update(iseSetting.name, iseSetting.value, true);
@@ -63,6 +70,7 @@ export class ISECompatibilityFeature implements vscode.Disposable {
     }
 
     private async DisableISEMode() {
+        this._iseModeEnabled = false;
         for (const iseSetting of ISECompatibilityFeature.settings) {
             const currently = vscode.workspace.getConfiguration(iseSetting.path).get<string | boolean>(iseSetting.name);
             if (currently === iseSetting.value) {
@@ -70,4 +78,12 @@ export class ISECompatibilityFeature implements vscode.Disposable {
             }
         }
     }
+
+    private async ToggleISEMode() {
+        if (this._iseModeEnabled) {
+            await this.DisableISEMode();
+        } else {
+            await this.EnableISEMode();
+        }
+    }
 }
diff --git a/test/features/ISECompatibility.test.ts b/test/features/ISECompatibility.test.ts
index d93adca2e0..64782db7ed 100644
--- a/test/features/ISECompatibility.test.ts
+++ b/test/features/ISECompatibility.test.ts
@@ -11,6 +11,7 @@ describe("ISE compatibility feature", function () {
 
     async function enableISEMode() { await vscode.commands.executeCommand("PowerShell.EnableISEMode"); }
     async function disableISEMode() { await vscode.commands.executeCommand("PowerShell.DisableISEMode"); }
+    async function toggleISEMode() { await vscode.commands.executeCommand("PowerShell.ToggleISEMode"); }
 
     before(async function () {
         // Save user's current theme.
@@ -24,7 +25,7 @@ describe("ISE compatibility feature", function () {
         assert.strictEqual(vscode.workspace.getConfiguration("workbench").get("colorTheme"), currentTheme);
     });
 
-    describe("EnableISEMode command", async function () {
+    describe("Enable ISE Mode updates expected settings", async function () {
         before(enableISEMode);
         after(disableISEMode);
         for (const iseSetting of ISECompatibilityFeature.settings) {
@@ -35,17 +36,42 @@ describe("ISE compatibility feature", function () {
         }
     });
 
-    describe("DisableISEMode command", async function () {
+    describe("Disable ISE Mode reverts expected settings", async function () {
         before(enableISEMode);
         before(disableISEMode);
+        after(disableISEMode);
+        for (const iseSetting of ISECompatibilityFeature.settings) {
+            it(`Reverts ${iseSetting.name} correctly`, function () {
+                const currently = vscode.workspace.getConfiguration(iseSetting.path).get(iseSetting.name);
+                assert.notStrictEqual(currently, iseSetting.value);
+            });
+        }
+    });
+
+    describe("Toggle switches from enabled to disabled", async function () {
+        before(enableISEMode);
+        before(toggleISEMode);
+        after(disableISEMode);
         for (const iseSetting of ISECompatibilityFeature.settings) {
-            it(`Unsets ${iseSetting.name} correctly`, function () {
+            it(`Reverts ${iseSetting.name} correctly`, function () {
                 const currently = vscode.workspace.getConfiguration(iseSetting.path).get(iseSetting.name);
                 assert.notStrictEqual(currently, iseSetting.value);
             });
         }
     });
 
+    describe("Toggle switches from disabled to enabled", async function () {
+        before(disableISEMode);
+        before(toggleISEMode);
+        after(disableISEMode);
+        for (const iseSetting of ISECompatibilityFeature.settings) {
+            it(`Sets ${iseSetting.name} correctly`, function () {
+                const currently = vscode.workspace.getConfiguration(iseSetting.path).get(iseSetting.name);
+                assert.strictEqual(currently, iseSetting.value);
+            });
+        }
+    });
+
     describe("Color theme interactions", async function () {
         beforeEach(enableISEMode);