diff --git a/src/agents/pi-embedded-runner/run/attempt.ts b/src/agents/pi-embedded-runner/run/attempt.ts
index e83c3ae4a..622bdb7f4 100644
--- a/src/agents/pi-embedded-runner/run/attempt.ts
+++ b/src/agents/pi-embedded-runner/run/attempt.ts
@@ -52,6 +52,7 @@ import {
 import { DEFAULT_BOOTSTRAP_FILENAME } from "../../workspace.js";
 import { buildSystemPromptReport } from "../../system-prompt-report.js";
 import { resolveDefaultModelForAgent } from "../../model-selection.js";
+import { sanitizeToolUseResultPairing } from "../../session-transcript-repair.js";
 
 import { isAbortError } from "../abort.js";
 import { buildEmbeddedExtensionPaths } from "../extensions.js";
@@ -535,9 +536,11 @@ export async function runEmbeddedAttempt(
           validated,
           getDmHistoryLimitFromSessionKey(params.sessionKey, params.config),
         );
-        cacheTrace?.recordStage("session:limited", { messages: limited });
-        if (limited.length > 0) {
-          activeSession.agent.replaceMessages(limited);
+        // Fix: Repair tool_use/tool_result pairings AFTER truncation (issue #4367)
+        const repaired = sanitizeToolUseResultPairing(limited);
+        cacheTrace?.recordStage("session:limited", { messages: repaired });
+        if (repaired.length > 0) {
+          activeSession.agent.replaceMessages(repaired);
         }
       } catch (err) {
         sessionManager.flushPendingToolResults?.();
diff --git a/src/agents/subagent-announce.ts b/src/agents/subagent-announce.ts
index 444726efc..46d902e80 100644
--- a/src/agents/subagent-announce.ts
+++ b/src/agents/subagent-announce.ts
@@ -192,6 +192,41 @@ async function maybeQueueSubagentAnnounce(params: {
   return "none";
 }
 
+/**
+ * Build a descriptive error status label from outcome data.
+ * Includes error type, message, and hint if available.
+ */
+function buildErrorStatusLabel(outcome: SubagentRunOutcome): string {
+  const parts: string[] = [];
+
+  // Start with "failed"
+  parts.push("failed");
+
+  // Add error type context
+  if (outcome.errorType) {
+    const typeLabel: Record<string, string> = {
+      model: "API error",
+      tool: "tool error",
+      network: "network error",
+      config: "configuration error",
+      timeout: "timeout",
+    };
+    const label = typeLabel[outcome.errorType] || "error";
+    parts.push(`(${label}):`);
+  }
+
+  // Add error message
+  const errorMsg = outcome.error || "unknown error";
+  parts.push(errorMsg);
+
+  // Add hint if available
+  if (outcome.errorHint) {
+    parts.push(`— ${outcome.errorHint}`);
+  }
+
+  return parts.join(" ");
+}
+
 async function buildSubagentStatsLine(params: {
   sessionKey: string;
   startedAt?: number;
@@ -299,6 +334,8 @@ export function buildSubagentSystemPrompt(params: {
 export type SubagentRunOutcome = {
   status: "ok" | "error" | "timeout" | "unknown";
   error?: string;
+  errorType?: "model" | "tool" | "network" | "config" | "timeout" | "unknown";
+  errorHint?: string;
 };
 
 export async function runSubagentAnnounceFlow(params: {
@@ -380,7 +417,7 @@ export async function runSubagentAnnounceFlow(params: {
         : outcome.status === "timeout"
           ? "timed out"
           : outcome.status === "error"
-            ? `failed: ${outcome.error || "unknown error"}`
+            ? buildErrorStatusLabel(outcome)
             : "finished with unknown status";
 
     // Build instructional message for main agent
diff --git a/src/agents/subagent-registry.ts b/src/agents/subagent-registry.ts
index d325e40e2..dca685b72 100644
--- a/src/agents/subagent-registry.ts
+++ b/src/agents/subagent-registry.ts
@@ -184,7 +184,16 @@ function ensureListener() {
     entry.endedAt = endedAt;
     if (phase === "error") {
       const error = typeof evt.data?.error === "string" ? (evt.data.error as string) : undefined;
-      entry.outcome = { status: "error", error };
+      const errorType =
+        typeof evt.data?.errorType === "string" ? (evt.data.errorType as string) : undefined;
+      const errorHint =
+        typeof evt.data?.errorHint === "string" ? (evt.data.errorHint as string) : undefined;
+      entry.outcome = {
+        status: "error",
+        error,
+        errorType: errorType as SubagentRunOutcome["errorType"],
+        errorHint,
+      };
     } else {
       entry.outcome = { status: "ok" };
     }
diff --git a/src/auto-reply/reply/agent-runner-execution.ts b/src/auto-reply/reply/agent-runner-execution.ts
index 21732f49f..36305bc68 100644
--- a/src/auto-reply/reply/agent-runner-execution.ts
+++ b/src/auto-reply/reply/agent-runner-execution.ts
@@ -51,6 +51,85 @@ export type AgentRunLoopResult =
     }
   | { kind: "final"; payload: ReplyPayload };
 
+/**
+ * Categorize errors to provide better error messages to users.
+ * Returns error message, type, and optional hint for remediation.
+ */
+function categorizeError(err: unknown): {
+  message: string;
+  type: "model" | "tool" | "network" | "config" | "timeout" | "unknown";
+  hint?: string;
+} {
+  const message = err instanceof Error ? err.message : String(err);
+
+  // File system errors
+  if (message.includes("ENOENT") || message.includes("ENOTDIR")) {
+    return { message, type: "tool", hint: "File or directory not found" };
+  }
+  if (message.includes("EACCES") || message.includes("EPERM")) {
+    return { message, type: "tool", hint: "Permission denied" };
+  }
+  if (message.includes("EISDIR")) {
+    return { message, type: "tool", hint: "Expected file but found directory" };
+  }
+
+  // API/Model errors
+  if (message.includes("rate limit") || message.includes("429")) {
+    return { message, type: "model", hint: "Rate limit exceeded - retry in a few moments" };
+  }
+  if (
+    message.includes("401") ||
+    message.includes("unauthorized") ||
+    message.includes("authentication")
+  ) {
+    return { message, type: "config", hint: "Check API credentials and permissions" };
+  }
+  if (message.includes("403") || message.includes("forbidden")) {
+    return { message, type: "config", hint: "Access denied - check permissions" };
+  }
+  if (message.includes("400") || message.includes("invalid request")) {
+    return { message, type: "model", hint: "Invalid request parameters" };
+  }
+  if (message.includes("500") || message.includes("503")) {
+    return { message, type: "model", hint: "API service error - try again later" };
+  }
+  if (message.includes("quota") || message.includes("billing")) {
+    return { message, type: "config", hint: "Check billing and API quota limits" };
+  }
+
+  // Network errors
+  if (message.includes("ECONNREFUSED") || message.includes("ETIMEDOUT")) {
+    return { message, type: "network", hint: "Connection failed - check network connectivity" };
+  }
+  if (message.includes("ENOTFOUND") || message.includes("DNS") || message.includes("EAI_AGAIN")) {
+    return { message, type: "network", hint: "DNS resolution failed - check hostname" };
+  }
+  if (message.includes("ENETUNREACH") || message.includes("EHOSTUNREACH")) {
+    return { message, type: "network", hint: "Network unreachable - check connection" };
+  }
+
+  // Timeout errors
+  if (
+    message.toLowerCase().includes("timeout") ||
+    message.toLowerCase().includes("timed out") ||
+    message.includes("ETIMEDOUT")
+  ) {
+    return { message, type: "timeout", hint: "Operation took too long - try increasing timeout" };
+  }
+
+  // Context/memory errors
+  if (message.includes("context") && message.includes("too large")) {
+    return { message, type: "model", hint: "Conversation too long - try clearing history" };
+  }
+
+  // Missing environment/config
+  if (message.includes("missing") && (message.includes("key") || message.includes("token"))) {
+    return { message, type: "config", hint: "Missing required configuration or credentials" };
+  }
+
+  return { message, type: "unknown" };
+}
+
 export async function runAgentTurnWithFallback(params: {
   commandBody: string;
   followupRun: FollowupRun;
@@ -204,6 +283,7 @@ export async function runAgentTurnWithFallback(params: {
                 return result;
               })
               .catch((err) => {
+                const { message, type, hint } = categorizeError(err);
                 emitAgentEvent({
                   runId,
                   stream: "lifecycle",
@@ -211,7 +291,9 @@ export async function runAgentTurnWithFallback(params: {
                     phase: "error",
                     startedAt,
                     endedAt: Date.now(),
-                    error: err instanceof Error ? err.message : String(err),
+                    error: message,
+                    errorType: type,
+                    errorHint: hint,
                   },
                 });
                 throw err;
diff --git a/src/cli/cron-cli/shared.test.ts b/src/cli/cron-cli/shared.test.ts
new file mode 100644
index 000000000..17cd1fd8b
--- /dev/null
+++ b/src/cli/cron-cli/shared.test.ts
@@ -0,0 +1,105 @@
+import { describe, expect, it, vi } from "vitest";
+import type { CronJob } from "../../cron/types.js";
+import { parseDurationMs, printCronList } from "./shared.js";
+
+// Minimal CronJob factory
+function makeCronJob(overrides: Partial<CronJob> & Record<string, unknown> = {}): CronJob {
+  return {
+    id: "test-id-000",
+    name: "test-job",
+    enabled: true,
+    createdAtMs: Date.now(),
+    updatedAtMs: Date.now(),
+    schedule: { kind: "every", everyMs: 60_000 },
+    sessionTarget: "isolated",
+    wakeMode: "prompt",
+    payload: { prompt: "hello" },
+    state: {},
+    ...overrides,
+  } as CronJob;
+}
+
+describe("printCronList", () => {
+  const captureLog = () => {
+    const lines: string[] = [];
+    const runtime = {
+      log: vi.fn((msg: string) => lines.push(msg)),
+      error: vi.fn(),
+    };
+    return { lines, runtime };
+  };
+
+  it("prints 'No cron jobs.' for empty list", () => {
+    const { runtime } = captureLog();
+    printCronList([], runtime as never);
+    expect(runtime.log).toHaveBeenCalledWith("No cron jobs.");
+  });
+
+  it("handles job with standard id property", () => {
+    const { lines, runtime } = captureLog();
+    const job = makeCronJob({ id: "abc-123" });
+    printCronList([job], runtime as never);
+    // Header + 1 job line
+    expect(lines).toHaveLength(2);
+    expect(lines[1]).toContain("abc-123");
+  });
+
+  it("handles job with jobId instead of id (Gateway API variant)", () => {
+    const { lines, runtime } = captureLog();
+    // Simulate Gateway returning jobId instead of id
+    const job = makeCronJob({ id: undefined as unknown as string, jobId: "gateway-456" } as never);
+    printCronList([job], runtime as never);
+    expect(lines).toHaveLength(2);
+    expect(lines[1]).toContain("gateway-456");
+  });
+
+  it("prefers jobId over id when both are present", () => {
+    const { lines, runtime } = captureLog();
+    const job = makeCronJob({ id: "fallback-id", jobId: "preferred-jobid" } as never);
+    printCronList([job], runtime as never);
+    expect(lines).toHaveLength(2);
+    expect(lines[1]).toContain("preferred-jobid");
+    expect(lines[1]).not.toContain("fallback-id");
+  });
+
+  it("does not crash when both id and jobId are missing", () => {
+    const { lines, runtime } = captureLog();
+    const job = makeCronJob({ id: undefined as unknown as string });
+    printCronList([job], runtime as never);
+    // Should not throw and should still print a line
+    expect(lines).toHaveLength(2);
+  });
+
+  it("prints multiple jobs", () => {
+    const { lines, runtime } = captureLog();
+    const jobs = [
+      makeCronJob({ id: "job-1", name: "first" }),
+      makeCronJob({ id: "job-2", name: "second" }),
+    ];
+    printCronList(jobs, runtime as never);
+    // Header + 2 job lines
+    expect(lines).toHaveLength(3);
+  });
+});
+
+describe("parseDurationMs", () => {
+  it.each([
+    ["1s", 1000],
+    ["5m", 300_000],
+    ["2h", 7_200_000],
+    ["1d", 86_400_000],
+    ["500ms", 500],
+    ["1.5s", 1500],
+  ])("parses %s → %d", (input, expected) => {
+    expect(parseDurationMs(input)).toBe(expected);
+  });
+
+  it("returns null for empty string", () => {
+    expect(parseDurationMs("")).toBeNull();
+  });
+
+  it("returns null for invalid input", () => {
+    expect(parseDurationMs("abc")).toBeNull();
+    expect(parseDurationMs("-5s")).toBeNull();
+  });
+});
diff --git a/src/cli/cron-cli/shared.ts b/src/cli/cron-cli/shared.ts
index 5e5efc81a..2e3ddaa61 100644
--- a/src/cli/cron-cli/shared.ts
+++ b/src/cli/cron-cli/shared.ts
@@ -141,7 +141,9 @@ export function printCronList(jobs: CronJob[], runtime = defaultRuntime) {
   const now = Date.now();
 
   for (const job of jobs) {
-    const idLabel = pad(job.id, CRON_ID_PAD);
+    // Gateway may return either 'id' or 'jobId' depending on API version
+    const id = (job as CronJob & { jobId?: string }).jobId ?? job.id ?? "";
+    const idLabel = pad(id, CRON_ID_PAD);
     const nameLabel = pad(truncate(job.name, CRON_NAME_PAD), CRON_NAME_PAD);
     const scheduleLabel = pad(
       truncate(formatSchedule(job.schedule), CRON_SCHEDULE_PAD),