diff --git a/app/api/chat/route.ts b/app/api/chat/route.ts
index 954da1b9..60276393 100644
--- a/app/api/chat/route.ts
+++ b/app/api/chat/route.ts
@@ -579,6 +579,83 @@ function lastToolResultsHadFailure(messages: ChatMessage[], lookback = 3) {
   return false;
 }
 
+// Pull a short, human-readable error out of the most recent failing tool
+// result so the build-health status can say WHAT broke (not just "didn't
+// reach a clean stopping point"). Secrets are already redacted upstream.
+function extractLastToolFailure(
+  messages: ChatMessage[],
+  lookback = 4,
+): string | null {
+  const toolMsgs = messages.filter((m) => m.role === "tool").slice(-lookback);
+  const clean = (s: string) => s.replace(/\s+/g, " ").trim().slice(0, 160);
+  for (let i = toolMsgs.length - 1; i >= 0; i--) {
+    const raw =
+      typeof toolMsgs[i].content === "string"
+        ? (toolMsgs[i].content as string)
+        : "";
+    if (!raw) continue;
+    try {
+      const p = JSON.parse(raw);
+      if (typeof p.error === "string" && p.error.trim()) return clean(p.error);
+      if (typeof p.exitCode === "number" && p.exitCode !== 0)
+        return clean(
+          `${p.stderr || p.stdout || "command failed"} (exit ${p.exitCode})`,
+        );
+      if (typeof p.code === "number" && p.code !== 0)
+        return clean(
+          `${p.stderr || p.stdout || "command failed"} (exit ${p.code})`,
+        );
+      if (p.healthCheck?.status && p.healthCheck.status >= 400)
+        return clean(`health check returned ${p.healthCheck.status}`);
+      if (p.ok === false && typeof p.message === "string")
+        return clean(p.message);
+    } catch {
+      if (/(econnrefused|enoent|error|failed|exception)/i.test(raw))
+        return clean(raw);
+    }
+  }
+  return null;
+}
+
+// Deterministic, STRUCTURED build-health status used when the model's own
+// wrap-up comes back empty. Replaces the old vague "didn't reach a clean
+// stopping point" line with: what happened + the specific blocker + a clear
+// next action.
+function buildHealthStatus(opts: {
+  loopBreakReason?: string | null;
+  hitRoundCap: boolean;
+  lastError: string | null;
+  toolCount: number;
+}): string {
+  const { loopBreakReason, hitRoundCap, lastError, toolCount } = opts;
+
+  if (lastError) {
+    return (
+      `I ran ${toolCount} step${toolCount === 1 ? "" : "s"} but hit a blocker: ` +
+      `**${lastError}**. I didn't want to claim success on top of that. ` +
+      `Want me to fix that specific issue and retry?`
+    );
+  }
+  if (loopBreakReason) {
+    return (
+      `I kept hitting the same wall while working on this (${loopBreakReason}), ` +
+      `so I stopped rather than spin. Want me to try a different approach, ` +
+      `or take a look together?`
+    );
+  }
+  if (hitRoundCap) {
+    return (
+      `I made progress across ${toolCount} step${toolCount === 1 ? "" : "s"} but ran out ` +
+      `of room this turn before finishing. Say "continue" and I'll pick up ` +
+      `exactly where I left off.`
+    );
+  }
+  return (
+    `I worked through ${toolCount} step${toolCount === 1 ? "" : "s"} but didn't land a ` +
+    `clean result. Want me to keep going, or take a different angle?`
+  );
+}
+
 export async function POST(request: Request) {
   await ensureChatTables();
 
@@ -1374,11 +1451,17 @@ export async function POST(request: Request) {
               assistantTextSegments.push(summary.text);
               emit({ type: "text", text: summary.text });
             } else {
-              // Gemini returned empty — fall back to a deterministic
-              // status so the user never sees silent ✓ pills.
-              const fallback = loopBreakReason
-                ? `I hit a loop while working on this — ${loopBreakReason}. Want me to try a different approach, or do you want to take a look?`
-                : `I ran a chain of ${assistantToolCalls.length} tool calls but didn't reach a clean stopping point. Want me to keep going, or take a different angle?`;
+              // Gemini returned empty — fall back to a deterministic but
+              // STRUCTURED build-health status (never a vague "didn't reach a
+              // clean stopping point"). It states what happened, what broke,
+              // and the next action, using the same signals as the telemetry
+              // stop_reason.
+              const fallback = buildHealthStatus({
+                loopBreakReason,
+                hitRoundCap: maxToolRounds > 0 && round >= maxToolRounds,
+                lastError: extractLastToolFailure(messages),
+                toolCount: assistantToolCalls.length,
+              });
               assistantText += (assistantText ? "\n\n" : "") + fallback;
               assistantTextSegments.push(fallback);
               emit({ type: "text", text: fallback });
@@ -1387,7 +1470,12 @@ export async function POST(request: Request) {
               emit({ type: "thinking", text: summary.thoughts });
             }
           } catch {
-            const fallback = `I ran ${assistantToolCalls.length} tool calls but the wrap-up failed. Want me to retry, or try a different approach?`;
+            const fallback = buildHealthStatus({
+              loopBreakReason,
+              hitRoundCap: maxToolRounds > 0 && round >= maxToolRounds,
+              lastError: extractLastToolFailure(messages),
+              toolCount: assistantToolCalls.length,
+            });
             assistantText += (assistantText ? "\n\n" : "") + fallback;
             assistantTextSegments.push(fallback);
             emit({ type: "text", text: fallback });
diff --git a/components/project/project-icon-rail.tsx b/components/project/project-icon-rail.tsx
index 64f79aa1..0f8a608d 100644
--- a/components/project/project-icon-rail.tsx
+++ b/components/project/project-icon-rail.tsx
@@ -210,12 +210,22 @@ function RailLink({
       aria-current={active ? "page" : undefined}
       style={{
         ...linkBase,
+        // Active item shows its label so the user always knows which mode
+        // they're in; inactive items stay icon-only (with tooltip) to save
+        // space. This makes the editor's modes explicit instead of a row of
+        // unlabeled glyphs.
+        width: active ? "auto" : 36,
+        padding: active ? "0 12px" : 0,
+        gap: active ? 6 : 0,
+        fontSize: "0.8rem",
+        fontWeight: 600,
         background: active ? "#f6f2ec" : "transparent",
         color: active ? "#1a1a1a" : "#6b665e",
         borderColor: active ? "#d9d2c5" : "transparent",
       }}
     >
       <Icon size={16} />
+      {active && <span>{label}</span>}
     </Link>
   );
 }
diff --git a/components/vibn-chat/chat-panel.tsx b/components/vibn-chat/chat-panel.tsx
index 07b7c22b..e0b1a765 100644
--- a/components/vibn-chat/chat-panel.tsx
+++ b/components/vibn-chat/chat-panel.tsx
@@ -230,6 +230,73 @@ function friendlyToolName(name: string): string {
   return map[dotted] || dotted;
 }
 
+/**
+ * Turn a raw tool result string (often a JSON blob like
+ * `{ "code": 1, "stdout": "...", "stderr": "..." }`) into a short,
+ * human-readable status. We NEVER show raw JSON in the chat — only a
+ * clean verb + outcome (e.g. "Failed — exit 1: connection refused").
+ */
+function summarizeToolResult(result?: string): {
+  ok: boolean;
+  label: string;
+} | null {
+  if (!result) return null;
+  const raw = String(result).trim();
+  if (!raw) return null;
+
+  let parsed: Record<string, unknown> | null = null;
+  try {
+    const p = JSON.parse(raw);
+    if (p && typeof p === "object") parsed = p as Record<string, unknown>;
+  } catch {
+    // not JSON — fall through to text heuristics
+  }
+
+  const firstLine = (s: string) => s.replace(/\s+/g, " ").trim().slice(0, 80);
+
+  if (parsed) {
+    const code = parsed.code;
+    const stderr = typeof parsed.stderr === "string" ? parsed.stderr : "";
+    const stdout = typeof parsed.stdout === "string" ? parsed.stdout : "";
+    const errMsg = typeof parsed.error === "string" ? parsed.error : "";
+
+    // Explicit non-zero exit code → failure
+    if (typeof code === "number" && code !== 0) {
+      const detail = firstLine(stderr || errMsg || stdout);
+      return {
+        ok: false,
+        label: detail
+          ? `Failed (exit ${code}) — ${detail}`
+          : `Failed (exit ${code})`,
+      };
+    }
+    if (errMsg && !/^null$/i.test(errMsg)) {
+      return { ok: false, label: `Failed — ${firstLine(errMsg)}` };
+    }
+    if (parsed.ok === false) {
+      return {
+        ok: false,
+        label: `Failed${stderr ? " — " + firstLine(stderr) : ""}`,
+      };
+    }
+    // Success-ish: surface a tiny hint when available, else just "Done"
+    if (typeof code === "number" && code === 0)
+      return { ok: true, label: "Done" };
+    return { ok: true, label: "Done" };
+  }
+
+  // Plain-text heuristics
+  const lower = raw.toLowerCase();
+  if (
+    /(econnrefused|enoent|error|failed|traceback|exception|not found|permission denied|cannot)/.test(
+      lower,
+    )
+  ) {
+    return { ok: false, label: `Failed — ${firstLine(raw)}` };
+  }
+  return { ok: true, label: "Done" };
+}
+
 // ── Markdown-lite renderer ────────────────────────────────────────────────────
 
 function escapeHtmlAttr(s: string): string {
@@ -850,20 +917,26 @@ function TimelineToolGroup({
               {!e.result && e.status === "running" && (
                 <span className="animate-pulse">...</span>
               )}
-              {e.result && (
-                <span
-                  style={{
-                    overflow: "hidden",
-                    textOverflow: "ellipsis",
-                    whiteSpace: "nowrap",
-                    opacity: 0.7,
-                    maxWidth: 150,
-                  }}
-                  title={e.result}
-                >
-                  — {e.result}
-                </span>
-              )}
+              {(() => {
+                // Render a clean, human summary of the outcome — never raw JSON.
+                const summary = summarizeToolResult(e.result);
+                if (!summary) return null;
+                return (
+                  <span
+                    style={{
+                      overflow: "hidden",
+                      textOverflow: "ellipsis",
+                      whiteSpace: "nowrap",
+                      maxWidth: 220,
+                      color: summary.ok ? "#6b8e6b" : "#c2554d",
+                      opacity: 0.9,
+                    }}
+                    title={summary.label}
+                  >
+                    — {summary.label}
+                  </span>
+                );
+              })()}
             </div>
           ))}
         </div>