diff --git a/apps/server/src/orchestration/Layers/ProviderRuntimeIngestion.ts b/apps/server/src/orchestration/Layers/ProviderRuntimeIngestion.ts
index 2c07ac91b1e..38766b63201 100644
--- a/apps/server/src/orchestration/Layers/ProviderRuntimeIngestion.ts
+++ b/apps/server/src/orchestration/Layers/ProviderRuntimeIngestion.ts
@@ -545,6 +545,7 @@ function runtimeEventToActivities(
           kind: "tool.updated",
           summary: event.payload.title ?? "Tool updated",
           payload: {
+            ...(event.itemId ? { itemId: event.itemId } : {}),
             itemType: event.payload.itemType,
             ...(event.payload.status ? { status: event.payload.status } : {}),
             ...(event.payload.detail ? { detail: truncateDetail(event.payload.detail) } : {}),
@@ -568,8 +569,9 @@ function runtimeEventToActivities(
           kind: "tool.completed",
           summary: event.payload.title ?? "Tool",
           payload: {
+            ...(event.itemId ? { itemId: event.itemId } : {}),
             itemType: event.payload.itemType,
-            ...(event.payload.detail ? { detail: truncateDetail(event.payload.detail) } : {}),
+            ...(event.payload.detail ? { detail: event.payload.detail } : {}),
             ...(event.payload.data !== undefined ? { data: event.payload.data } : {}),
           },
           turnId: toTurnId(event.turnId) ?? null,
@@ -588,10 +590,11 @@ function runtimeEventToActivities(
           createdAt: event.createdAt,
           tone: "tool",
           kind: "tool.started",
-          summary: `${event.payload.title ?? "Tool"} started`,
+          summary: event.payload.title ?? "Tool started",
           payload: {
+            ...(event.itemId ? { itemId: event.itemId } : {}),
             itemType: event.payload.itemType,
-            ...(event.payload.detail ? { detail: truncateDetail(event.payload.detail) } : {}),
+            ...(event.payload.detail ? { detail: event.payload.detail } : {}),
           },
           turnId: toTurnId(event.turnId) ?? null,
           ...maybeSequence,
diff --git a/apps/server/src/provider/Layers/CodexAdapter.ts b/apps/server/src/provider/Layers/CodexAdapter.ts
index 28af1cda27b..83951c8c5d4 100644
--- a/apps/server/src/provider/Layers/CodexAdapter.ts
+++ b/apps/server/src/provider/Layers/CodexAdapter.ts
@@ -235,7 +235,7 @@ function toCanonicalItemType(raw: string | undefined | null): CanonicalItemType
   return "unknown";
 }
 
-function itemTitle(itemType: CanonicalItemType): string | undefined {
+function itemTitle(itemType: CanonicalItemType, started = false): string | undefined {
   switch (itemType) {
     case "assistant_message":
       return "Assistant message";
@@ -246,7 +246,7 @@ function itemTitle(itemType: CanonicalItemType): string | undefined {
     case "plan":
       return "Plan";
     case "command_execution":
-      return "Ran command";
+      return started ? "Running command" : "Ran command";
     case "file_change":
       return "File change";
     case "mcp_tool_call":
@@ -469,6 +469,7 @@ function mapItemLifecycle(
       : lifecycle === "item.completed"
         ? "completed"
         : undefined;
+  const title = itemTitle(itemType, lifecycle === "item.started");
 
   return {
     ...runtimeEventBase(event, canonicalThreadId),
@@ -476,7 +477,7 @@ function mapItemLifecycle(
     payload: {
       itemType,
       ...(status ? { status } : {}),
-      ...(itemTitle(itemType) ? { title: itemTitle(itemType) } : {}),
+      ...(title ? { title } : {}),
       ...(detail ? { detail } : {}),
       ...(event.payload !== undefined ? { data: event.payload } : {}),
     },
diff --git a/apps/web/src/session-logic.ts b/apps/web/src/session-logic.ts
index a7767672fa1..07ba656abdb 100644
--- a/apps/web/src/session-logic.ts
+++ b/apps/web/src/session-logic.ts
@@ -58,7 +58,9 @@ export interface WorkLogEntry {
   tone: "thinking" | "tool" | "info" | "error";
   toolTitle?: string;
   itemType?: ToolLifecycleItemType;
+  itemId?: string;
   requestKind?: PendingApproval["requestKind"];
+  collapseKey?: string;
 }
 
 interface DerivedWorkLogEntry extends WorkLogEntry {
@@ -487,14 +489,13 @@ export function deriveWorkLogEntries(
   const ordered = [...activities].toSorted(compareActivitiesByOrder);
   const entries = ordered
     .filter((activity) => (latestTurnId ? activity.turnId === latestTurnId : true))
-    .filter((activity) => activity.kind !== "tool.started")
     .filter((activity) => activity.kind !== "task.started")
     .filter((activity) => activity.kind !== "context-window.updated")
     .filter((activity) => activity.summary !== "Checkpoint captured")
     .filter((activity) => !isPlanBoundaryToolActivity(activity))
     .map(toDerivedWorkLogEntry);
   return collapseDerivedWorkLogEntries(entries).map(
-    ({ activityKind: _activityKind, collapseKey: _collapseKey, ...entry }) => entry,
+    ({ activityKind: _activityKind, ...entry }) => entry,
   );
 }
 
@@ -553,6 +554,7 @@ function toDerivedWorkLogEntry(activity: OrchestrationThreadActivity): DerivedWo
     activityKind: activity.kind,
   };
   const itemType = extractWorkLogItemType(payload);
+  const itemId = extractWorkLogItemId(payload);
   const requestKind = extractWorkLogRequestKind(payload);
   if (detail) {
     entry.detail = detail;
@@ -572,6 +574,9 @@ function toDerivedWorkLogEntry(activity: OrchestrationThreadActivity): DerivedWo
   if (itemType) {
     entry.itemType = itemType;
   }
+  if (itemId) {
+    entry.itemId = itemId;
+  }
   if (requestKind) {
     entry.requestKind = requestKind;
   }
@@ -589,13 +594,28 @@ function collapseDerivedWorkLogEntries(
   entries: ReadonlyArray<DerivedWorkLogEntry>,
 ): DerivedWorkLogEntry[] {
   const collapsed: DerivedWorkLogEntry[] = [];
+  const openLifecycleRowIndexByCollapseKey = new Map<string, number>();
   for (const entry of entries) {
-    const previous = collapsed.at(-1);
-    if (previous && shouldCollapseToolLifecycleEntries(previous, entry)) {
-      collapsed[collapsed.length - 1] = mergeDerivedWorkLogEntries(previous, entry);
-      continue;
+    const collapseKey = entry.collapseKey;
+    if (collapseKey) {
+      const openIndex = openLifecycleRowIndexByCollapseKey.get(collapseKey);
+      if (openIndex !== undefined) {
+        const previous = collapsed[openIndex];
+        if (previous && shouldCollapseToolLifecycleEntries(previous, entry)) {
+          collapsed[openIndex] = mergeDerivedWorkLogEntries(previous, entry);
+          if (entry.activityKind === "tool.completed") {
+            openLifecycleRowIndexByCollapseKey.delete(collapseKey);
+          }
+          continue;
+        }
+      }
     }
+
     collapsed.push(entry);
+    if (collapseKey && (entry.activityKind === "tool.started" || entry.activityKind === "tool.updated")) {
+      openLifecycleRowIndexByCollapseKey.set(collapseKey, collapsed.length - 1);
+      continue;
+    }
   }
   return collapsed;
 }
@@ -604,7 +624,7 @@ function shouldCollapseToolLifecycleEntries(
   previous: DerivedWorkLogEntry,
   next: DerivedWorkLogEntry,
 ): boolean {
-  if (previous.activityKind !== "tool.updated" && previous.activityKind !== "tool.completed") {
+  if (previous.activityKind !== "tool.started" && previous.activityKind !== "tool.updated" && previous.activityKind !== "tool.completed") {
     return false;
   }
   if (next.activityKind !== "tool.updated" && next.activityKind !== "tool.completed") {
@@ -641,6 +661,8 @@ function mergeDerivedWorkLogEntries(
   return {
     ...previous,
     ...next,
+    id: previous.id,
+    createdAt: previous.createdAt,
     ...(detail ? { detail } : {}),
     ...(command ? { command } : {}),
     ...(rawCommand ? { rawCommand } : {}),
@@ -665,19 +687,23 @@ function mergeChangedFiles(
 }
 
 function deriveToolLifecycleCollapseKey(entry: DerivedWorkLogEntry): string | undefined {
-  if (entry.activityKind !== "tool.updated" && entry.activityKind !== "tool.completed") {
+  if (entry.activityKind !== "tool.started" && entry.activityKind !== "tool.updated" && entry.activityKind !== "tool.completed") {
     return undefined;
   }
   if (entry.toolCallId) {
     return `tool:${entry.toolCallId}`;
   }
+  const itemId = entry.itemId?.trim() ?? "";
+  if (itemId.length > 0) {
+    return itemId;
+  }
   const normalizedLabel = normalizeCompactToolLabel(entry.toolTitle ?? entry.label);
-  const detail = entry.detail?.trim() ?? "";
+  const commandOrDetail = (entry.command ?? entry.detail)?.trim() ?? "";
   const itemType = entry.itemType ?? "";
-  if (normalizedLabel.length === 0 && detail.length === 0 && itemType.length === 0) {
+  if (normalizedLabel.length === 0 && commandOrDetail.length === 0 && itemType.length === 0) {
     return undefined;
   }
-  return [itemType, normalizedLabel, detail].join("\u001f");
+  return [itemType, normalizedLabel, commandOrDetail].join("\u001f");
 }
 
 function normalizeCompactToolLabel(value: string): string {
@@ -1030,6 +1056,10 @@ function extractWorkLogItemType(
   return undefined;
 }
 
+function extractWorkLogItemId(payload: Record<string, unknown> | null): string | undefined {
+  return typeof payload?.itemId === "string" && payload.itemId.length > 0 ? payload.itemId : undefined;
+}
+
 function extractWorkLogRequestKind(
   payload: Record<string, unknown> | null,
 ): WorkLogEntry["requestKind"] | undefined {