diff --git a/web/src/components/chat/MessageList.tsx b/web/src/components/chat/MessageList.tsx
index cf9e390..9dca5de 100644
--- a/web/src/components/chat/MessageList.tsx
+++ b/web/src/components/chat/MessageList.tsx
@@ -2,6 +2,7 @@ import { AlertCircleIcon } from "lucide-react";
 import { useMemo, type ReactNode } from "react";
 import type { AgentMessage, PendingTool, ToolExecution, ToolResultContentPart } from "@/lib/pi-events";
 import { contentText } from "@/lib/pi-events";
+import { friendlyErrorMessage } from "@/lib/error-messages";
 import { MessageShell } from "@/components/chat-ui/MessageShell";
 import { ZeroLoader } from "@/components/chat-ui/ZeroLoader";
 import { MessageView } from "./pi-transcript";
@@ -183,7 +184,7 @@ export function MessageList({
         <MessageShell role="assistant">
           <div className="flex items-center gap-3 text-destructive text-sm">
             <AlertCircleIcon className="size-4 shrink-0" />
-            <span>Something went wrong.</span>
+            <span>{friendlyErrorMessage(error.message)}</span>
           </div>
         </MessageShell>
       )}
diff --git a/web/src/components/chat/pi-transcript/MessageView.tsx b/web/src/components/chat/pi-transcript/MessageView.tsx
index b514f85..2a04df4 100644
--- a/web/src/components/chat/pi-transcript/MessageView.tsx
+++ b/web/src/components/chat/pi-transcript/MessageView.tsx
@@ -7,6 +7,7 @@ import type {
   UserMessage,
 } from "@/lib/pi-events";
 import { contentText } from "@/lib/pi-events";
+import { friendlyErrorMessage } from "@/lib/error-messages";
 import { MessageShell } from "@/components/chat-ui/MessageShell";
 import { Markdown } from "@/components/chat-ui/Markdown";
 import { ToolCallCard } from "./ToolCallCard";
@@ -147,7 +148,9 @@ function AssistantMessageView({
           {message.stopReason === "aborted" ? (
             <div className="text-sm text-muted-foreground italic">Agent was interrupted.</div>
           ) : (
-            <div className="text-sm text-destructive">{message.errorMessage}</div>
+            <div className="text-sm text-destructive">
+              {friendlyErrorMessage(message.errorMessage)}
+            </div>
           )}
         </MessageShell>
       )}
diff --git a/web/src/lib/error-messages.ts b/web/src/lib/error-messages.ts
new file mode 100644
index 0000000..ec3d357
--- /dev/null
+++ b/web/src/lib/error-messages.ts
@@ -0,0 +1,50 @@
+/**
+ * Chat errors arrive from the server as raw technical strings (an exception's
+ * `err.message`: stack-y SDK errors, HTTP status text, provider payloads). We
+ * don't want to surface those verbatim — they're noise to the user and can leak
+ * internals. This maps a raw error to a short, generic, user-facing line.
+ *
+ * A few broad, genuinely-actionable categories get a tailored (but still
+ * non-technical) message; everything else falls back to a single generic line.
+ */
+const GENERIC = "Something went wrong. Please try again.";
+
+const CATEGORIES: Array<{ match: RegExp; message: string }> = [
+  {
+    // Rate limits / provider overload (429, "overloaded", "capacity").
+    match: /\b(429|rate.?limit|overloaded|too many requests|capacity)\b/i,
+    message: "The service is busy right now. Please try again in a moment.",
+  },
+  {
+    // Network / connectivity failures.
+    match: /\b(network|fetch failed|econnrefused|enotfound|econnreset|socket|offline|dns)\b/i,
+    message: "Connection problem. Please check your network and try again.",
+  },
+  {
+    // Request took too long.
+    match: /\b(timed?.?out|timeout|etimedout|deadline)\b/i,
+    message: "The request timed out. Please try again.",
+  },
+  {
+    // Conversation exceeded the model's context window.
+    match: /\b(context length|context window|too many tokens|maximum.*tokens|token limit)\b/i,
+    message: "This conversation is too long for the model. Try starting a new chat.",
+  },
+  {
+    // Auth / permission issues.
+    match: /\b(401|403|unauthorized|forbidden|invalid api key|authentication)\b/i,
+    message: "There was an authentication problem. Please reconnect and try again.",
+  },
+];
+
+/**
+ * Turn a raw error string into a generic, user-facing message. Returns the
+ * generic fallback when the input is empty or unrecognized.
+ */
+export function friendlyErrorMessage(raw?: string | null): string {
+  if (!raw) return GENERIC;
+  for (const { match, message } of CATEGORIES) {
+    if (match.test(raw)) return message;
+  }
+  return GENERIC;
+}
diff --git a/web/src/pages/CanvasPage.tsx b/web/src/pages/CanvasPage.tsx
index 8dda24b..8cdb614 100644
--- a/web/src/pages/CanvasPage.tsx
+++ b/web/src/pages/CanvasPage.tsx
@@ -793,6 +793,20 @@ export function CanvasPage() {
           onPointerMove={onCanvasPointerMove}
           onWheel={onWheel}
         >
+          {/* Background dot grid — pans and zooms with the view. */}
+          <defs>
+            <pattern
+              id="canvas-dots"
+              width={24 * view.scale}
+              height={24 * view.scale}
+              patternUnits="userSpaceOnUse"
+              patternTransform={`translate(${view.tx} ${view.ty})`}
+            >
+              <circle cx={1} cy={1} r={1} fill="currentColor" className="text-border" />
+            </pattern>
+          </defs>
+          <rect x={0} y={0} width="100%" height="100%" fill="url(#canvas-dots)" pointerEvents="none" />
+
           <g transform={`translate(${view.tx} ${view.ty}) scale(${view.scale})`}>
             {list.map((s) => (
               <ShapeView
@@ -880,13 +894,6 @@ export function CanvasPage() {
           />
         )}
 
-        {list.length === 0 && (
-          <div className="pointer-events-none absolute inset-0 flex items-center justify-center">
-            <p className="text-sm text-muted-foreground">
-              Pick a tool and click to start — or ask the agent to draw here.
-            </p>
-          </div>
-        )}
       </div>
 
       <AlertDialog open={confirmClearOpen} onOpenChange={setConfirmClearOpen}>