@stigmer/react 3.0.8-dev.20260613041848 → 3.0.8-dev.20260613051837

package/session/useSessionConversation.d.ts

@@ -114,11 +114,28 @@ export interface UseSessionConversationReturn {
     readonly canSendFollowUp: boolean;
     /** True during the create RPC call (between submit and execution ID). */
     readonly isSending: boolean;
-    /** Error from the last sendFollowUp attempt, or null. */
+    /**
+     * Error from the last `sendFollowUp` attempt, or `null`.
+     *
+     * Covers **both** failing paths — the optional `session.update()` and the
+     * `create()` RPC — so a follow-up never fails silently. When set, the user's
+     * message is preserved (see {@link pendingUserMessage}) and can be re-sent
+     * via {@link retryLastSend}.
+     */
     readonly sendError: Error | null;
-    /** Reset `sendError` to `null`. */
+    /** Reset `sendError` to `null` (keeps the preserved pending message). */
     readonly clearSendError: () => void;
-    /** The user's message text, shown in the thread before the stream delivers it. */
+    /**
+     * Re-send the most recent `sendFollowUp` (same message and options). No-op
+     * when nothing has been sent yet. Use as the "Retry" affordance on a failed
+     * turn; clears {@link sendError} for the new attempt.
+     */
+    readonly retryLastSend: () => void;
+    /**
+     * The user's message text, shown in the thread before the stream delivers it.
+     * Retained when a send fails so the typed message is never lost — pair with
+     * {@link sendError} to render the turn as failed with a retry control.
+     */
     readonly pendingUserMessage: string | null;
     /** Current workspace entries from the session spec. Empty array when session is not loaded. */
     readonly workspaceEntries: readonly ProtoWorkspaceEntry[];
@@ -146,6 +163,20 @@ export interface UseSessionConversationReturn {
      * surface a subtle "Reconnecting…" hint rather than an error banner.
      */
     readonly isReconnecting: boolean;
+    /**
+     * `true` when the stream opened but never delivered a first snapshot within
+     * the watchdog window (even after a silent retry) — the agent hasn't started.
+     * Distinct from `streamError`: nothing threw, the stream is simply silent.
+     * Surface an actionable "the agent hasn't started — Retry" banner wired to
+     * {@link reconnectStream}.
+     */
+    readonly connectTimedOut: boolean;
+    /**
+     * `true` when a live, non-terminal stream has been silent past the slow
+     * threshold. Purely informational ("still working — taking longer than
+     * usual"); cleared by the next update. Never an error.
+     */
+    readonly isSlow: boolean;
     /** Error from the execution stream, or `null` when healthy or reconnecting. */
     readonly streamError: Error | null;
     /** Reset the stream error and re-establish the execution stream subscription. */

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package/session/useSessionConversation.js

@@ -1,7 +1,8 @@
 "use client";
-import { useCallback, useEffect, useMemo, useState } from "react";
+import { useCallback, useEffect, useMemo, useRef, useState } from "react";
 import { isTerminalPhase } from "../execution/execution-phases";
 import { useStigmer } from "../hooks";
+import { toError } from "../internal/toError";
 import { useConversationStoreRef } from "../internal/store";
 import { useCreateAgentExecution } from "../execution/useCreateAgentExecution";
 import { useExecutionStream } from "../execution/useExecutionStream";
@@ -11,6 +12,13 @@ import { useSessionExecutions } from "./useSessionExecutions";
 import { useUpdateSession } from "./useUpdateSession";
 import { useLocalSessionWorker } from "./useLocalSessionWorker";
 import { specWorkspaceToInput, specMcpUsagesToInput, specSkillRefsToInput, } from "./session-spec-converters";
+/**
+ * Cadence for re-discovering the session's executions while the live stream
+ * cannot be relied on (a created-but-not-yet-listed execution, a silent
+ * connect-timeout, or an exhausted stream error). Disabled the instant the
+ * stream is healthy or terminal, so this never competes with the live feed.
+ */
+const REDISCOVERY_POLL_INTERVAL_MS = 5_000;
 /**
  * Behavior hook that encapsulates the full conversation lifecycle for
  * a session: loading data, streaming the active execution, submitting
@@ -62,8 +70,17 @@ import { specWorkspaceToInput, specMcpUsagesToInput, specSkillRefsToInput, } fro
 export function useSessionConversation(sessionId, org) {
     const stigmer = useStigmer();
     const { session, isLoading: sessionLoading, error: sessionError, refetch: refetchSession, } = useSession(sessionId);
-    const { executions, isLoading: executionsLoading, error: executionsError, refetch, } = useSessionExecutions(sessionId);
-    const { create, isCreating, error: createError, clearError: clearCreateError, } = useCreateAgentExecution();
+    // Bounded re-discovery (see REDISCOVERY_POLL_INTERVAL_MS). The gate depends on
+    // the stream below, so the decision is synced into state via an effect and fed
+    // back here on the next render — a one-frame lag that is immaterial at 5s.
+    const [rediscoveryActive, setRediscoveryActive] = useState(false);
+    const { executions, isLoading: executionsLoading, error: executionsError, refetch, } = useSessionExecutions(sessionId, {
+        refetchInterval: rediscoveryActive ? REDISCOVERY_POLL_INTERVAL_MS : false,
+        // Re-list on app-relaunch / tab refocus so an execution that appeared while
+        // backgrounded is picked up without the user having to act.
+        refetchOnWindowFocus: true,
+    });
+    const { create, isCreating, clearError: clearCreateError, } = useCreateAgentExecution();
     const { update: updateSession } = useUpdateSession();
     const { submitApproval: rawSubmitApproval, submittingToolCallIds, error: approvalError, clearError: clearApprovalError, } = useSubmitApproval();
     // Local execution: attach the session's runner worker while it is open and
@@ -71,6 +88,11 @@ export function useSessionConversation(sessionId, org) {
     useLocalSessionWorker(sessionId, session);
     const [pendingExecutionId, setPendingExecutionId] = useState(null);
     const [pendingUserMessage, setPendingUserMessage] = useState(null);
+    // Dedicated send-failure state, distinct from the create hook's internal
+    // error so it can also cover the session.update() path. The last send's
+    // arguments are captured for an exact retry.
+    const [sendError, setSendError] = useState(null);
+    const lastSendRef = useRef(null);
     const listActiveId = useMemo(() => {
         for (let i = executions.length - 1; i >= 0; i--) {
             const phase = executions[i].status?.phase;
@@ -89,6 +111,21 @@ export function useSessionConversation(sessionId, org) {
     const stream = useExecutionStream(activeExecutionId, {
         store: conversationStore,
     });
+    // Re-discovery gate. Poll only while the live stream cannot carry us:
+    //  • a fresh session whose first execution is created but not yet listed
+    //    (`executions.length === 0`) — the race this fix targets,
+    //  • a silent connect-timeout, or an exhausted stream error.
+    // Never while the stream is healthy (`isStreaming`) or the active execution
+    // has reached a terminal phase — the live feed is then the source of truth.
+    const streamTerminal = activeExecutionId !== null && isTerminalPhase(stream.phase);
+    const needsRediscovery = !stream.isStreaming &&
+        !streamTerminal &&
+        ((activeExecutionId === null && executions.length === 0) ||
+            stream.connectTimedOut ||
+            stream.error !== null);
+    useEffect(() => {
+        setRediscoveryActive(needsRediscovery);
+    }, [needsRediscovery]);
     // Clear pendingExecutionId once the execution appears in the fetched list
     useEffect(() => {
         if (pendingExecutionId &&
@@ -96,12 +133,20 @@ export function useSessionConversation(sessionId, org) {
             setPendingExecutionId(null);
         }
     }, [pendingExecutionId, executions]);
-    // Clear optimistic message once the stream delivers its first snapshot
+    // Clear the optimistic message — and any stale send error — once the stream
+    // delivers a real snapshot. This also handles recovery: if a failed send's
+    // execution is later re-discovered and streams, the failed turn resolves into
+    // the live one instead of lingering. (At send time the composer is only
+    // enabled when no execution is active, so a *fresh* failure cannot be cleared
+    // here prematurely — `stream.execution` is null then.)
     useEffect(() => {
-        if (pendingUserMessage && stream.execution) {
+        if (!stream.execution)
+            return;
+        if (pendingUserMessage)
             setPendingUserMessage(null);
-        }
-    }, [pendingUserMessage, stream.execution]);
+        if (sendError)
+            setSendError(null);
+    }, [pendingUserMessage, sendError, stream.execution]);
     // Refetch executions when stream reaches a terminal phase so the
     // fetched list reflects the completed status and listActiveId clears.
     useEffect(() => {
@@ -132,6 +177,9 @@ export function useSessionConversation(sessionId, org) {
     const sendFollowUp = useCallback(async (message, options) => {
         if (!sessionId || !session)
             return;
+        // Capture for retry and clear any prior failure before the new attempt.
+        lastSendRef.current = { message, options };
+        setSendError(null);
         setPendingUserMessage(message);
         try {
             const needsSessionUpdate = options?.agentInstanceId !== undefined ||
@@ -166,12 +214,24 @@ export function useSessionConversation(sessionId, org) {
             refetch();
         }
         catch (err) {
-            setPendingUserMessage(null);
+            // Surface the failure and KEEP the user's message visible (do not clear
+            // pendingUserMessage) so the turn renders as failed-with-retry instead
+            // of vanishing. Covers both the update() and create() paths.
+            setSendError(toError(err));
             if (process.env.NODE_ENV !== "production") {
                 console.error("[useSessionConversation] sendFollowUp failed:", err);
             }
         }
     }, [sessionId, session, org, stigmer, create, updateSession, refetch, refetchSession]);
+    const retryLastSend = useCallback(() => {
+        const last = lastSendRef.current;
+        if (last)
+            void sendFollowUp(last.message, last.options);
+    }, [sendFollowUp]);
+    const clearSendError = useCallback(() => {
+        setSendError(null);
+        clearCreateError();
+    }, [clearCreateError]);
     const pendingApprovals = useMemo(() => activeStreamExecution?.status?.pendingApprovals ?? [], [activeStreamExecution]);
     const submitApproval = useCallback(async (toolCallId, action, comment) => {
         if (!activeExecutionId)
@@ -190,8 +250,9 @@ export function useSessionConversation(sessionId, org) {
         sendFollowUp,
         canSendFollowUp,
         isSending: isCreating,
-        sendError: createError,
-        clearSendError: clearCreateError,
+        sendError,
+        clearSendError,
+        retryLastSend,
         pendingUserMessage,
         workspaceEntries,
         mcpServerUsages,
@@ -204,6 +265,8 @@ export function useSessionConversation(sessionId, org) {
         isLoading,
         loadError,
         isReconnecting: stream.isReconnecting,
+        connectTimedOut: stream.connectTimedOut,
+        isSlow: stream.isSlow,
         streamError: stream.error,
         reconnectStream: stream.reconnect,
     };

package/session/useSessionConversation.js.map

@@ -1 +1 @@
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package/session/useSessionExecutions.d.ts

@@ -1,4 +1,20 @@
 import type { AgentExecution } from "@stigmer/protos/ai/stigmer/agentic/agentexecution/v1/api_pb";
+/** Options for {@link useSessionExecutions}. */
+export interface UseSessionExecutionsOptions {
+    /**
+     * Poll interval in milliseconds for re-listing the session's executions.
+     * Used by the conversation loop to re-discover a created-but-not-yet-listed
+     * execution. Pass `false` (the default) to disable polling and rely on the
+     * live stream plus imperative {@link UseSessionExecutionsReturn.refetch}.
+     */
+    readonly refetchInterval?: number | false;
+    /**
+     * Re-list when the window regains focus / the tab becomes visible — covers
+     * the app-relaunch case where an execution may have appeared while
+     * backgrounded. Defaults to `false`.
+     */
+    readonly refetchOnWindowFocus?: boolean;
+}
 /** Return value of {@link useSessionExecutions}. */
 export interface UseSessionExecutionsReturn {
     /** All executions for the session, empty while loading or on error. */
@@ -46,5 +62,5 @@ export interface UseSessionExecutionsReturn {
  * const { executions } = useSessionExecutions(sessionId ?? null);
  * ```
  */
-export declare function useSessionExecutions(sessionId: string | null): UseSessionExecutionsReturn;
+export declare function useSessionExecutions(sessionId: string | null, options?: UseSessionExecutionsOptions): UseSessionExecutionsReturn;
 //# sourceMappingURL=useSessionExecutions.d.ts.map

package/session/useSessionExecutions.d.ts.map

@@ -1 +1 @@
-{"version":3,"file":"useSessionExecutions.d.ts","sourceRoot":"","sources":["../../src/session/useSessionExecutions.ts"],"names":[],"mappings":"AAGA,OAAO,KAAK,EAAE,cAAc,EAAE,MAAM,6DAA6D,CAAC;AAKlG,oDAAoD;AACpD,MAAM,WAAW,0BAA0B;IACzC,uEAAuE;IACvE,QAAQ,CAAC,UAAU,EAAE,SAAS,cAAc,EAAE,CAAC;IAC/C,mDAAmD;IACnD,QAAQ,CAAC,SAAS,EAAE,OAAO,CAAC;IAC5B,sDAAsD;IACtD,QAAQ,CAAC,YAAY,EAAE,OAAO,CAAC;IAC/B,kEAAkE;IAClE,QAAQ,CAAC,KAAK,EAAE,KAAK,GAAG,IAAI,CAAC;IAC7B,2EAA2E;IAC3E,QAAQ,CAAC,OAAO,EAAE,MAAM,IAAI,CAAC;CAC9B;AAED;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;GAiCG;AACH,wBAAgB,oBAAoB,CAClC,SAAS,EAAE,MAAM,GAAG,IAAI,GACvB,0BAA0B,CAqB5B"}
+{"version":3,"file":"useSessionExecutions.d.ts","sourceRoot":"","sources":["../../src/session/useSessionExecutions.ts"],"names":[],"mappings":"AAGA,OAAO,KAAK,EAAE,cAAc,EAAE,MAAM,6DAA6D,CAAC;AAKlG,gDAAgD;AAChD,MAAM,WAAW,2BAA2B;IAC1C;;;;;OAKG;IACH,QAAQ,CAAC,eAAe,CAAC,EAAE,MAAM,GAAG,KAAK,CAAC;IAC1C;;;;OAIG;IACH,QAAQ,CAAC,oBAAoB,CAAC,EAAE,OAAO,CAAC;CACzC;AAED,oDAAoD;AACpD,MAAM,WAAW,0BAA0B;IACzC,uEAAuE;IACvE,QAAQ,CAAC,UAAU,EAAE,SAAS,cAAc,EAAE,CAAC;IAC/C,mDAAmD;IACnD,QAAQ,CAAC,SAAS,EAAE,OAAO,CAAC;IAC5B,sDAAsD;IACtD,QAAQ,CAAC,YAAY,EAAE,OAAO,CAAC;IAC/B,kEAAkE;IAClE,QAAQ,CAAC,KAAK,EAAE,KAAK,GAAG,IAAI,CAAC;IAC7B,2EAA2E;IAC3E,QAAQ,CAAC,OAAO,EAAE,MAAM,IAAI,CAAC;CAC9B;AAED;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;GAiCG;AACH,wBAAgB,oBAAoB,CAClC,SAAS,EAAE,MAAM,GAAG,IAAI,EACxB,OAAO,CAAC,EAAE,2BAA2B,GACpC,0BAA0B,CAyB5B"}

package/session/useSessionExecutions.js

@@ -37,7 +37,7 @@ import { useFetch } from "../internal/useFetch";
  * const { executions } = useSessionExecutions(sessionId ?? null);
  * ```
  */
-export function useSessionExecutions(sessionId) {
+export function useSessionExecutions(sessionId, options) {
     const stigmer = useStigmer();
     const { data: executions, isLoading, isRefetching, error, refetch } = useFetch(sessionId
         ? () => stigmer.agentExecution
@@ -46,7 +46,11 @@ export function useSessionExecutions(sessionId) {
             pageSize: 100,
         }))
             .then((result) => result.entries)
-        : null, [sessionId, stigmer], [], { cacheKey: sessionId ? `session-executions:${sessionId}` : undefined });
+        : null, [sessionId, stigmer], [], {
+        cacheKey: sessionId ? `session-executions:${sessionId}` : undefined,
+        refetchInterval: options?.refetchInterval,
+        refetchOnWindowFocus: options?.refetchOnWindowFocus,
+    });
     return { executions, isLoading, isRefetching, error, refetch };
 }
 //# sourceMappingURL=useSessionExecutions.js.map

package/session/useSessionExecutions.js.map

@@ -1 +1 @@
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+{"version":3,"file":"useSessionExecutions.js","sourceRoot":"","sources":["../../src/session/useSessionExecutions.ts"],"names":[],"mappings":"AAAA,YAAY,CAAC;AAEb,OAAO,EAAE,MAAM,EAAE,MAAM,oBAAoB,CAAC;AAE5C,OAAO,EAAE,yCAAyC,EAAE,MAAM,4DAA4D,CAAC;AACvH,OAAO,EAAE,UAAU,EAAE,MAAM,UAAU,CAAC;AACtC,OAAO,EAAE,QAAQ,EAAE,MAAM,sBAAsB,CAAC;AAiChD;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;GAiCG;AACH,MAAM,UAAU,oBAAoB,CAClC,SAAwB,EACxB,OAAqC;IAErC,MAAM,OAAO,GAAG,UAAU,EAAE,CAAC;IAE7B,MAAM,EAAE,IAAI,EAAE,UAAU,EAAE,SAAS,EAAE,YAAY,EAAE,KAAK,EAAE,OAAO,EAAE,GAAG,QAAQ,CAC5E,SAAS;QACP,CAAC,CAAC,GAAG,EAAE,CACH,OAAO,CAAC,cAAc;aACnB,aAAa,CACZ,MAAM,CAAC,yCAAyC,EAAE;YAChD,SAAS;YACT,QAAQ,EAAE,GAAG;SACd,CAAC,CACH;aACA,IAAI,CAAC,CAAC,MAAM,EAAE,EAAE,CAAC,MAAM,CAAC,OAAO,CAAC;QACvC,CAAC,CAAC,IAAI,EACR,CAAC,SAAS,EAAE,OAAO,CAAC,EACpB,EAAsB,EACtB;QACE,QAAQ,EAAE,SAAS,CAAC,CAAC,CAAC,sBAAsB,SAAS,EAAE,CAAC,CAAC,CAAC,SAAS;QACnE,eAAe,EAAE,OAAO,EAAE,eAAe;QACzC,oBAAoB,EAAE,OAAO,EAAE,oBAAoB;KACpD,CACF,CAAC;IAEF,OAAO,EAAE,UAAU,EAAE,SAAS,EAAE,YAAY,EAAE,KAAK,EAAE,OAAO,EAAE,CAAC;AACjE,CAAC"}

package/src/execution/ExecutionProgress.tsx

@@ -47,6 +47,10 @@ export function ExecutionProgress({
   if (phase === undefined) return null;
 
   const todos = execution.status?.todos;
+  // Populated by the server only on EXECUTION_FAILED — surface it next to the
+  // badge so this widget explains a failure rather than showing a bare phase
+  // (consistent with the failure reason in the message thread).
+  const error = execution.status?.error;
 
   return (
     <div
@@ -55,6 +59,14 @@ export function ExecutionProgress({
       aria-label="Execution progress"
     >
       <ExecutionPhaseBadge phase={phase} />
+      {error && (
+        <p
+          role="alert"
+          className="text-xs whitespace-pre-wrap break-words text-destructive"
+        >
+          {error}
+        </p>
+      )}
       {todos && <TodoList todos={todos} />}
     </div>
   );

package/src/execution/MessageThread.tsx

@@ -1,6 +1,6 @@
 "use client";
 
-import { lazy, memo, Suspense, useCallback, useMemo } from "react";
+import { lazy, memo, Suspense, useCallback, useMemo, useState } from "react";
 import { create } from "@bufbuild/protobuf";
 import type { AgentExecution } from "@stigmer/protos/ai/stigmer/agentic/agentexecution/v1/api_pb";
 import type { AgentMessage, ToolCall } from "@stigmer/protos/ai/stigmer/agentic/agentexecution/v1/message_pb";
@@ -60,6 +60,27 @@ export interface MessageThreadProps {
    * first snapshot.
    */
   readonly pendingUserMessage?: string | null;
+  /**
+   * Marks the pending user message as failed-to-send. The optimistic
+   * bubble renders an inline "Couldn't send — Retry" affordance instead
+   * of the sending indicator, so a failed follow-up never silently
+   * vanishes. Pair with {@link onRetrySend}.
+   *
+   * @default false
+   */
+  readonly pendingMessageFailed?: boolean;
+  /**
+   * Retry handler for a failed pending message. Wired to the inline
+   * "Retry" control when {@link pendingMessageFailed} is `true`.
+   */
+  readonly onRetrySend?: () => void;
+  /**
+   * Retry handler for a terminal-failed execution that exposed a server
+   * error reason. Receives the originating message; the consumer typically
+   * resends it as a new execution. When omitted, no Retry control is shown
+   * beside the surfaced failure reason.
+   */
+  readonly onRetryExecution?: (message: string) => void;
   /** Additional CSS class names for the root container. */
   readonly className?: string;
   /**
@@ -178,10 +199,11 @@ export interface MessageThreadProps {
  * part of the public API.
  */
 export type ThreadItem =
-  | { readonly kind: "message"; readonly message: AgentMessage; readonly key: string; readonly isPending?: boolean }
+  | { readonly kind: "message"; readonly message: AgentMessage; readonly key: string; readonly isPending?: boolean; readonly isFailed?: boolean }
   | { readonly kind: "tool-group"; readonly toolCalls: readonly ToolCall[]; readonly subAgentExecutions: readonly SubAgentExecution[]; readonly key: string }
   | { readonly kind: "sub-agent"; readonly subAgentExecution: SubAgentExecution; readonly key: string }
   | { readonly kind: "phase-badge"; readonly phase: ExecutionPhase; readonly key: string }
+  | { readonly kind: "execution-error"; readonly error: string; readonly retryMessage?: string; readonly key: string }
   | { readonly kind: "approval-request"; readonly pendingApproval: PendingApproval; readonly key: string }
   | { readonly kind: "setup-progress"; readonly workspaceEntries: readonly WorkspaceEntry[]; readonly serverPhase?: string; readonly isAwaitingResponse?: boolean; readonly key: string }
   | { readonly kind: "context-compacted"; readonly event: SummarizationEventView; readonly key: string }
@@ -216,6 +238,7 @@ export function buildThreadItems(
   includeApprovals: boolean,
   workspaceEntries: readonly WorkspaceEntry[] | undefined,
   summarizationEvents?: readonly SummarizationEventView[],
+  pendingMessageFailed = false,
 ): ThreadItem[] {
   const items: ThreadItem[] = [];
   const allExecutions = activeStreamExecution
@@ -393,6 +416,22 @@ export function buildThreadItems(
       phase: lastPhase,
       key: `phase-${lastPhase}`,
     });
+
+    // The server populates `status.error` only on EXECUTION_FAILED. Surface it
+    // beside the badge so a failure that produced no messages still explains
+    // itself (the CLI shows this reason; the chat previously showed nothing).
+    // Kept as its own item so the badge component stays presentational.
+    const reason = lastExec?.status?.error;
+    if (reason) {
+      const specMessage = lastExec?.spec?.message;
+      items.push({
+        kind: "execution-error",
+        error: reason,
+        retryMessage:
+          specMessage && specMessage !== "execute" ? specMessage : undefined,
+        key: `execution-error-${lastExec?.metadata?.id ?? lastPhase}`,
+      });
+    }
   }
 
   if (
@@ -430,7 +469,10 @@ export function buildThreadItems(
         kind: "message",
         message: syntheticPending,
         key: "pending-user-turn",
-        isPending: true,
+        // A failed turn shows the inline error instead of the dimmed
+        // sending state — the two are mutually exclusive.
+        isPending: !pendingMessageFailed,
+        isFailed: pendingMessageFailed,
       });
     }
   }
@@ -465,6 +507,9 @@ export function MessageThread({
   executions,
   activeStreamExecution,
   pendingUserMessage,
+  pendingMessageFailed = false,
+  onRetrySend,
+  onRetryExecution,
   className,
   formatToolCallSummary,
   onApprovalSubmit,
@@ -483,8 +528,8 @@ export function MessageThread({
 
   const includeApprovals = onApprovalSubmit != null;
   const items = useMemo(
-    () => buildThreadItems(executions, activeStreamExecution, pendingUserMessage, includeApprovals, workspaceEntries, summarizationEvents),
-    [executions, activeStreamExecution, pendingUserMessage, includeApprovals, workspaceEntries, summarizationEvents],
+    () => buildThreadItems(executions, activeStreamExecution, pendingUserMessage, includeApprovals, workspaceEntries, summarizationEvents, pendingMessageFailed),
+    [executions, activeStreamExecution, pendingUserMessage, includeApprovals, workspaceEntries, summarizationEvents, pendingMessageFailed],
   );
 
   useKeyStability(items);
@@ -517,6 +562,8 @@ export function MessageThread({
             org={org}
             planActionsDisabled={planActionsDisabled}
             centerContent={centerContent}
+            onRetrySend={onRetrySend}
+            onRetryExecution={onRetryExecution}
           />
         </Suspense>
       </div>
@@ -536,6 +583,8 @@ export function MessageThread({
       onBuildFromPlan={onBuildFromPlan}
       org={org}
       planActionsDisabled={planActionsDisabled}
+      onRetrySend={onRetrySend}
+      onRetryExecution={onRetryExecution}
     />
   );
 }
@@ -560,6 +609,8 @@ interface NonVirtualizedThreadProps {
   readonly onBuildFromPlan?: () => void;
   readonly org?: string;
   readonly planActionsDisabled?: boolean;
+  readonly onRetrySend?: () => void;
+  readonly onRetryExecution?: (message: string) => void;
 }
 
 function NonVirtualizedThread({
@@ -574,6 +625,8 @@ function NonVirtualizedThread({
   onBuildFromPlan,
   org,
   planActionsDisabled,
+  onRetrySend,
+  onRetryExecution,
 }: NonVirtualizedThreadProps) {
   const { scrollRef, sentinelRef, contentRef, isFollowing, jumpToLatest } =
     useAutoScroll();
@@ -609,6 +662,8 @@ function NonVirtualizedThread({
                   onBuildFromPlan={onBuildFromPlan}
                   org={org}
                   planActionsDisabled={planActionsDisabled}
+                  onRetrySend={onRetrySend}
+                  onRetryExecution={onRetryExecution}
                 />
               </ThreadItemWrapper>
             ))}
@@ -645,6 +700,8 @@ export interface ThreadItemRendererProps {
   readonly onBuildFromPlan?: () => void;
   readonly org?: string;
   readonly planActionsDisabled?: boolean;
+  readonly onRetrySend?: () => void;
+  readonly onRetryExecution?: (message: string) => void;
 }
 
 /**
@@ -666,9 +723,16 @@ export function ThreadItemRenderer({
   onBuildFromPlan,
   org,
   planActionsDisabled,
+  onRetrySend,
+  onRetryExecution,
 }: ThreadItemRendererProps) {
   switch (item.kind) {
     case "message":
+      if (item.isFailed) {
+        return (
+          <FailedUserMessage message={item.message} onRetry={onRetrySend} />
+        );
+      }
       return (
         <MessageEntry
           message={item.message}
@@ -697,6 +761,14 @@ export function ThreadItemRenderer({
           <ExecutionPhaseBadge phase={item.phase} />
         </div>
       );
+    case "execution-error":
+      return (
+        <ExecutionErrorNotice
+          error={item.error}
+          retryMessage={item.retryMessage}
+          onRetry={onRetryExecution}
+        />
+      );
     case "approval-request":
       return (
         <ApprovalCardRow
@@ -736,6 +808,103 @@ export function ThreadItemRenderer({
   }
 }
 
+// ---------------------------------------------------------------------------
+// FailedUserMessage — optimistic turn whose send failed
+// ---------------------------------------------------------------------------
+
+/**
+ * Renders a user message whose send failed: the message itself stays visible
+ * (so the typed text is never lost) with an inline, actionable error beneath
+ * it. The error copy is intentionally short — the full reason is surfaced by
+ * the consumer's send-error banner; this is the in-thread "Retry" affordance.
+ */
+function FailedUserMessage({
+  message,
+  onRetry,
+}: {
+  message: AgentMessage;
+  onRetry?: () => void;
+}) {
+  return (
+    <div className="flex flex-col gap-1">
+      <MessageEntry message={message} />
+      <div
+        role="alert"
+        className="mx-4 flex items-center gap-2 text-xs text-destructive"
+      >
+        <span className="min-w-0 flex-1 truncate">Couldn&rsquo;t send.</span>
+        {onRetry && (
+          <button
+            type="button"
+            onClick={onRetry}
+            className="shrink-0 rounded font-medium underline-offset-2 hover:underline focus-visible:outline-none focus-visible:ring-2 focus-visible:ring-ring"
+          >
+            Retry
+          </button>
+        )}
+      </div>
+    </div>
+  );
+}
+
+// ---------------------------------------------------------------------------
+// ExecutionErrorNotice — server failure reason for a terminal-failed execution
+// ---------------------------------------------------------------------------
+
+/**
+ * Renders the server-reported failure reason (`AgentExecutionStatus.error`)
+ * for an execution that died — typically before producing any messages. The
+ * reason can be a long Temporal error, so it is clamped by default with a
+ * Show more / Show less toggle. An optional Retry resends the originating
+ * message as a fresh execution.
+ */
+function ExecutionErrorNotice({
+  error,
+  retryMessage,
+  onRetry,
+}: {
+  error: string;
+  retryMessage?: string;
+  onRetry?: (message: string) => void;
+}) {
+  const [expanded, setExpanded] = useState(false);
+  const canRetry = !!onRetry && !!retryMessage;
+
+  return (
+    <div
+      role="alert"
+      className="mx-4 flex flex-col gap-1.5 rounded-md bg-destructive-subtle px-3 py-2"
+    >
+      <p
+        className={cn(
+          "text-xs whitespace-pre-wrap break-words text-destructive",
+          !expanded && "line-clamp-3",
+        )}
+      >
+        {error}
+      </p>
+      <div className="flex items-center gap-3 text-xs">
+        <button
+          type="button"
+          onClick={() => setExpanded((v) => !v)}
+          className="font-medium text-muted-foreground underline-offset-2 hover:underline focus-visible:outline-none focus-visible:ring-2 focus-visible:ring-ring"
+        >
+          {expanded ? "Show less" : "Show more"}
+        </button>
+        {canRetry && (
+          <button
+            type="button"
+            onClick={() => onRetry!(retryMessage!)}
+            className="font-medium text-foreground underline-offset-2 hover:underline focus-visible:outline-none focus-visible:ring-2 focus-visible:ring-ring"
+          >
+            Retry
+          </button>
+        )}
+      </div>
+    </div>
+  );
+}
+
 // ---------------------------------------------------------------------------
 // ApprovalCardRow — stabilizes the onSubmit callback for React.memo
 // ---------------------------------------------------------------------------