diff --git a/e2e/playwright/fixtures/sceneFixture.ts b/e2e/playwright/fixtures/sceneFixture.ts
index c054e9a08..06be6fdfc 100644
--- a/e2e/playwright/fixtures/sceneFixture.ts
+++ b/e2e/playwright/fixtures/sceneFixture.ts
@@ -44,6 +44,7 @@ export class SceneFixture {
   public page: Page
   public streamWrapper!: Locator
   public networkToggleConnected!: Locator
+  public engineConnectionsSpinner!: Locator
   public startEditSketchBtn!: Locator
 
   constructor(page: Page) {
@@ -52,6 +53,7 @@ export class SceneFixture {
     this.networkToggleConnected = page
       .getByTestId('network-toggle-ok')
       .or(page.getByTestId('network-toggle-other'))
+    this.engineConnectionsSpinner = page.getByTestId(`loading-engine`)
     this.startEditSketchBtn = page
       .getByRole('button', { name: 'Start Sketch' })
       .or(page.getByRole('button', { name: 'Edit Sketch' }))
@@ -228,6 +230,7 @@ export class SceneFixture {
   connectionEstablished = async () => {
     const timeout = 30000
     await expect(this.networkToggleConnected).toBeVisible({ timeout })
+    await expect(this.engineConnectionsSpinner).not.toBeVisible()
   }
 
   settled = async (cmdBar: CmdBarFixture) => {
@@ -235,6 +238,7 @@ export class SceneFixture {
 
     await expect(this.startEditSketchBtn).not.toBeDisabled({ timeout: 15_000 })
     await expect(this.startEditSketchBtn).toBeVisible()
+    await expect(this.engineConnectionsSpinner).not.toBeVisible()
 
     await cmdBar.openCmdBar()
     await cmdBar.chooseCommand('Settings · app · show debug panel')
diff --git a/src/components/EngineStream.tsx b/src/components/EngineStream.tsx
index 85c7e66b9..b08fb2a6e 100644
--- a/src/components/EngineStream.tsx
+++ b/src/components/EngineStream.tsx
@@ -5,7 +5,10 @@ import { useModelingContext } from '@src/hooks/useModelingContext'
 import { useNetworkContext } from '@src/hooks/useNetworkContext'
 import { NetworkHealthState } from '@src/hooks/useNetworkStatus'
 import { getArtifactOfTypes } from '@src/lang/std/artifactGraph'
-import { EngineCommandManagerEvents } from '@src/lang/std/engineConnection'
+import {
+  EngineCommandManagerEvents,
+  EngineConnectionStateType,
+} from '@src/lang/std/engineConnection'
 import { btnName } from '@src/lib/cameraControls'
 import { PATHS } from '@src/lib/paths'
 import { sendSelectEventToEngine } from '@src/lib/selections'
@@ -25,6 +28,7 @@ import {
   EngineStreamTransition,
 } from '@src/machines/engineStreamMachine'
 
+import Loading from '@src/components/Loading'
 import { useSelector } from '@xstate/react'
 import type { MouseEventHandler } from 'react'
 import { useEffect, useRef, useState } from 'react'
@@ -426,6 +430,12 @@ export const EngineStream = (props: {
         }
         menuTargetElement={videoWrapperRef}
       />
+      {engineCommandManager.engineConnection?.state.type !==
+        EngineConnectionStateType.ConnectionEstablished && (
+        <Loading dataTestId="loading-engine" className="fixed inset-0">
+          Connecting to engine
+        </Loading>
+      )}
     </div>
   )
 }
diff --git a/src/components/Loading.tsx b/src/components/Loading.tsx
index b9950069f..e2de68cf0 100644
--- a/src/components/Loading.tsx
+++ b/src/components/Loading.tsx
@@ -1,6 +1,10 @@
+import type { MarkedOptions } from '@ts-stack/markdown'
+import { Marked, escape, unescape } from '@ts-stack/markdown'
 import { useEffect, useState } from 'react'
 
+import { CustomIcon } from '@src/components/CustomIcon'
 import { Spinner } from '@src/components/Spinner'
+import type { ErrorType } from '@src/lang/std/engineConnection'
 import {
   CONNECTION_ERROR_TEXT,
   ConnectionError,
@@ -9,15 +13,33 @@ import {
   EngineConnectionEvents,
   EngineConnectionStateType,
 } from '@src/lang/std/engineConnection'
+import { SafeRenderer } from '@src/lib/markdown'
 import { engineCommandManager } from '@src/lib/singletons'
 
 interface LoadingProps extends React.PropsWithChildren {
   className?: string
+  dataTestId?: string
 }
 
-const Loading = ({ children, className }: LoadingProps) => {
-  const [error, setError] = useState<ConnectionError>(ConnectionError.Unset)
+const markedOptions: MarkedOptions = {
+  gfm: true,
+  breaks: true,
+  sanitize: true,
+  unescape,
+  escape,
+}
 
+const Loading = ({ children, className, dataTestId }: LoadingProps) => {
+  const [error, setError] = useState<ErrorType>({
+    error: ConnectionError.Unset,
+  })
+  const isUnrecoverableError = error.error > ConnectionError.VeryLongLoadingTime
+  const colorClass =
+    error.error === ConnectionError.Unset
+      ? 'text-primary'
+      : !isUnrecoverableError
+        ? 'text-warn-60'
+        : 'text-chalkboard-60 dark:text-chalkboard-40'
   useEffect(() => {
     const onConnectionStateChange = ({ detail: state }: CustomEvent) => {
       if (
@@ -26,7 +48,7 @@ const Loading = ({ children, className }: LoadingProps) => {
         state.value?.type !== DisconnectingType.Error
       )
         return
-      setError(state.value.value.error)
+      setError(state.value.value)
     }
 
     const onEngineAvailable = ({ detail: engineConnection }: CustomEvent) => {
@@ -36,10 +58,27 @@ const Loading = ({ children, className }: LoadingProps) => {
       )
     }
 
-    engineCommandManager.addEventListener(
-      EngineCommandManagerEvents.EngineAvailable,
-      onEngineAvailable as EventListener
-    )
+    if (engineCommandManager.engineConnection) {
+      // Do an initial state check in case there is an immediate issue
+      onConnectionStateChange(
+        new CustomEvent(EngineConnectionEvents.ConnectionStateChanged, {
+          detail: engineCommandManager.engineConnection.state,
+        })
+      )
+      // Set up a listener on the state for future updates
+      onEngineAvailable(
+        new CustomEvent(EngineCommandManagerEvents.EngineAvailable, {
+          detail: engineCommandManager.engineConnection,
+        })
+      )
+    } else {
+      // If there is no engine connection yet, listen for it to be there *then*
+      // attach the listener
+      engineCommandManager.addEventListener(
+        EngineCommandManagerEvents.EngineAvailable,
+        onEngineAvailable as EventListener
+      )
+    }
 
     return () => {
       engineCommandManager.removeEventListener(
@@ -55,30 +94,59 @@ const Loading = ({ children, className }: LoadingProps) => {
 
   useEffect(() => {
     // Don't set long loading time if there's a more severe error
-    if (error > ConnectionError.LongLoadingTime) return
+    if (isUnrecoverableError) return
 
-    const timer = setTimeout(() => {
-      setError(ConnectionError.LongLoadingTime)
+    const shorterTimer = setTimeout(() => {
+      setError({ error: ConnectionError.LongLoadingTime })
     }, 4000)
+    const longerTimer = setTimeout(() => {
+      setError({ error: ConnectionError.VeryLongLoadingTime })
+    }, 7000)
 
-    return () => clearTimeout(timer)
-  }, [error, setError])
+    return () => {
+      clearTimeout(shorterTimer)
+      clearTimeout(longerTimer)
+    }
+  }, [error, setError, isUnrecoverableError])
 
   return (
     <div
-      className={`body-bg flex flex-col items-center justify-center h-screen ${className}`}
-      data-testid="loading"
+      className={`body-bg flex flex-col items-center justify-center h-screen ${colorClass} ${className}`}
+      data-testid={dataTestId ? dataTestId : 'loading'}
     >
-      <Spinner />
-      <p className="text-base mt-4 text-primary">{children || 'Loading'}</p>
-      <p
-        className={
-          'text-sm mt-4 text-primary/60 transition-opacity duration-500' +
-          (error !== ConnectionError.Unset ? ' opacity-100' : ' opacity-0')
-        }
-      >
-        {CONNECTION_ERROR_TEXT[error]}
+      {isUnrecoverableError ? (
+        <CustomIcon
+          name="close"
+          className="w-8 h-8 !text-chalkboard-10 bg-destroy-60 rounded-full"
+        />
+      ) : (
+        <Spinner />
+      )}
+      <p className={`text-base mt-4`}>
+        {isUnrecoverableError ? 'An error occurred' : children || 'Loading'}
       </p>
+      {CONNECTION_ERROR_TEXT[error.error] && (
+        <div
+          className={
+            'text-center text-sm mt-4 text-opacity-70 transition-opacity duration-500' +
+            (error.error !== ConnectionError.Unset
+              ? ' opacity-100'
+              : ' opacity-0')
+          }
+          dangerouslySetInnerHTML={{
+            __html: Marked.parse(
+              CONNECTION_ERROR_TEXT[error.error] +
+                (error.context
+                  ? '\n\nThe error details are: ' + error.context
+                  : ''),
+              {
+                renderer: new SafeRenderer(markedOptions),
+                ...markedOptions,
+              }
+            ),
+          }}
+        ></div>
+      )}
     </div>
   )
 }
diff --git a/src/components/Spinner.tsx b/src/components/Spinner.tsx
index 539511f0c..fca2cc826 100644
--- a/src/components/Spinner.tsx
+++ b/src/components/Spinner.tsx
@@ -12,7 +12,7 @@ export const Spinner = (props: SVGProps<SVGSVGElement>) => {
         cx="5"
         cy="5"
         r="4"
-        stroke="var(--primary)"
+        stroke="currentColor"
         fill="none"
         strokeDasharray="4, 4"
         className="animate-spin origin-center"
diff --git a/src/lang/std/engineConnection.ts b/src/lang/std/engineConnection.ts
index fbc6e5df7..05c795042 100644
--- a/src/lang/std/engineConnection.ts
+++ b/src/lang/std/engineConnection.ts
@@ -67,6 +67,7 @@ export enum DisconnectingType {
 export enum ConnectionError {
   Unset = 0,
   LongLoadingTime,
+  VeryLongLoadingTime,
 
   ICENegotiate,
   DataChannelError,
@@ -78,6 +79,7 @@ export enum ConnectionError {
   MissingAuthToken,
   BadAuthToken,
   TooManyConnections,
+  Outage,
 
   // An unknown error is the most severe because it has not been classified
   // or encountered before.
@@ -88,6 +90,8 @@ export const CONNECTION_ERROR_TEXT: Record<ConnectionError, string> = {
   [ConnectionError.Unset]: '',
   [ConnectionError.LongLoadingTime]:
     'Loading is taking longer than expected...',
+  [ConnectionError.VeryLongLoadingTime]:
+    'Loading seems stuck. Do you have a firewall turned on?',
   [ConnectionError.ICENegotiate]: 'ICE negotiation failed.',
   [ConnectionError.DataChannelError]: 'The data channel signaled an error.',
   [ConnectionError.WebSocketError]: 'The websocket signaled an error.',
@@ -97,7 +101,10 @@ export const CONNECTION_ERROR_TEXT: Record<ConnectionError, string> = {
     'Your authorization token is missing; please login again.',
   [ConnectionError.BadAuthToken]:
     'Your authorization token is invalid; please login again.',
-  [ConnectionError.TooManyConnections]: 'There are too many connections.',
+  [ConnectionError.TooManyConnections]:
+    'There are too many open engine connections associated with your account.',
+  [ConnectionError.Outage]:
+    'We seem to be experiencing an outage. Please visit [status.zoo.dev](https://status.zoo.dev) for updates.',
   [ConnectionError.Unknown]:
     'An unexpected error occurred. Please report this to us.',
 }
@@ -1002,6 +1009,20 @@ class EngineConnection extends EventTarget {
               }
               this.disconnectAll()
             }
+
+            if (firstError.error_code === 'internal_api') {
+              this.state = {
+                type: EngineConnectionStateType.Disconnecting,
+                value: {
+                  type: DisconnectingType.Error,
+                  value: {
+                    error: ConnectionError.Outage,
+                    context: firstError.message,
+                  },
+                },
+              }
+              this.disconnectAll()
+            }
             return
           }