diff --git a/package.json b/package.json
index 2f762db75..353090c10 100644
--- a/package.json
+++ b/package.json
@@ -59,6 +59,15 @@
   "main": "./out/extension.js",
   "runme": {
     "features": {
+      "HostedPlayground": {
+        "enabled": false,
+        "conditions": {
+          "enabledForExtensions": {
+            "stateful.platform": false,
+            "stateful.runme": true
+          }
+        }
+      },
       "NewTreeProvider": {
         "enabled": false,
         "conditions": {
diff --git a/src/extension/extension.ts b/src/extension/extension.ts
index 6482d5277..14f2ae2a8 100644
--- a/src/extension/extension.ts
+++ b/src/extension/extension.ts
@@ -94,6 +94,7 @@ import getLogger from './logger'
 import { EnvironmentManager } from './environment/manager'
 import ContextState from './contextState'
 import { RunmeIdentity } from './grpc/serializerTypes'
+import * as features from './features'
 
 export class RunmeExtension {
   protected serializer?: SerializerBase
@@ -532,6 +533,12 @@ export class RunmeExtension {
         })
       }
     })
+
+    // only ever enabled in hosted playground
+    if (features.isOnInContextState(FeatureName.HostedPlayground)) {
+      await features.addTrustedDomains()
+      await features.autoOpenTerminal()
+    }
   }
 
   protected handleMasking(kernel: Kernel, maskingIsOn: boolean): (e: NotebookUiEvent) => void {
diff --git a/src/extension/features/addTrustedDomains.ts b/src/extension/features/addTrustedDomains.ts
new file mode 100644
index 000000000..8b5dbca81
--- /dev/null
+++ b/src/extension/features/addTrustedDomains.ts
@@ -0,0 +1,37 @@
+import { Uri, workspace } from 'vscode'
+import { parse as jsoncParse } from 'jsonc-parser'
+
+import { FeatureName } from '../../types'
+import getLogger from '../logger'
+
+import { isOnInContextState } from '.'
+
+const logger = getLogger('AddTrustedDomains')
+const trustedDomain = 'https://*.stateful.com'
+
+export async function addTrustedDomains() {
+  if (!isOnInContextState(FeatureName.HostedPlayground)) {
+    return
+  }
+
+  try {
+    const uri = Uri.parse('trustedDomains:/Trusted Domains')
+    const bytes = await workspace.fs.readFile(uri)
+    const json = jsoncParse(Buffer.from(bytes).toString('utf8')) as string[]
+    const isTrusted = json.some((entry) => entry === trustedDomain)
+
+    if (!isTrusted) {
+      json.push(trustedDomain)
+      await workspace.fs.writeFile(uri, Buffer.from(JSON.stringify(json)))
+    }
+  } catch (error) {
+    let message
+    if (error instanceof Error) {
+      message = error.message
+    } else {
+      message = JSON.stringify(error)
+    }
+
+    logger.error(message)
+  }
+}
diff --git a/src/extension/features/autoOpenTerminal.ts b/src/extension/features/autoOpenTerminal.ts
new file mode 100644
index 000000000..c78746af7
--- /dev/null
+++ b/src/extension/features/autoOpenTerminal.ts
@@ -0,0 +1,17 @@
+import { commands } from 'vscode'
+
+import { FeatureName } from '../../types'
+import ContextState from '../contextState'
+
+import { isOnInContextState } from '.'
+
+export async function autoOpenTerminal() {
+  if (!isOnInContextState(FeatureName.HostedPlayground)) {
+    return
+  }
+
+  if (!ContextState.getKey<boolean>(`${FeatureName.HostedPlayground}.autoOpenTerminal`)) {
+    await commands.executeCommand('workbench.action.terminal.new')
+    await ContextState.addKey(`${FeatureName.HostedPlayground}.autoOpenTerminal`, true)
+  }
+}
diff --git a/src/extension/features.ts b/src/extension/features/index.ts
similarity index 72%
rename from src/extension/features.ts
rename to src/extension/features/index.ts
index ef665c0fc..dfb8411cf 100644
--- a/src/extension/features.ts
+++ b/src/extension/features/index.ts
@@ -1,7 +1,9 @@
-import features, { FEATURES_CONTEXT_STATE_KEY } from '../features'
-import { FeatureName } from '../types'
+export * from './addTrustedDomains'
+export * from './autoOpenTerminal'
 
-import ContextState from './contextState'
+import features, { FEATURES_CONTEXT_STATE_KEY } from '../../features'
+import { FeatureName } from '../../types'
+import ContextState from '../contextState'
 
 export function isOnInContextState(featureName: FeatureName): boolean {
   const snapshot = ContextState.getKey<string>(FEATURES_CONTEXT_STATE_KEY)
@@ -14,10 +16,6 @@ export function isOnInContextState(featureName: FeatureName): boolean {
   return features.isOn(featureName, featureState$)
 }
 
-export default {
-  isOnInContextState,
-}
-
 export function getFeaturesContext() {
   const snapshot = ContextState.getKey<string>(FEATURES_CONTEXT_STATE_KEY)
   if (!snapshot) {
@@ -28,3 +26,7 @@ export function getFeaturesContext() {
 
   return featureState$.getValue().context
 }
+
+export default {
+  isOnInContextState,
+}
diff --git a/src/types.ts b/src/types.ts
index ec453b969..00c290348 100644
--- a/src/types.ts
+++ b/src/types.ts
@@ -772,6 +772,7 @@ export enum FeatureName {
   RequireStatefulAuth = 'RequireStatefulAuth',
   CopySelectionToClipboard = 'CopySelectionToClipboard',
   NewTreeProvider = 'NewTreeProvider',
+  HostedPlayground = 'HostedPlayground',
 }
 
 export type Feature = {
diff --git a/tests/extension/features.test.ts b/tests/extension/features.test.ts
index 9d5c80bf8..028b4bec4 100644
--- a/tests/extension/features.test.ts
+++ b/tests/extension/features.test.ts
@@ -190,3 +190,33 @@ describe('Feature Store', () => {
     expect(features.isOn(FeatureName.Gist, featureState$)).toBe(true)
   })
 })
+
+describe('Hosted Playground', () => {
+  let featureState$: FeatureObserver
+
+  beforeEach(() => {
+    featureState$ = features.loadState(packageJSON, {
+      os: 'linux',
+    })
+  })
+
+  it('should always be default disabled in Runme', () => {
+    const initialContext: FeatureContext = {
+      extensionId: ExtensionName.StatefulRunme,
+    }
+
+    features.updateState(featureState$, initialContext)
+
+    expect(features.isOn(FeatureName.HostedPlayground, featureState$)).toBe(false)
+  })
+
+  it('should always be default disabled in Stateful', () => {
+    const initialContext: FeatureContext = {
+      extensionId: ExtensionName.StatefulPlatform,
+    }
+
+    features.updateState(featureState$, initialContext)
+
+    expect(features.isOn(FeatureName.HostedPlayground, featureState$)).toBe(false)
+  })
+})