diff --git a/hub/src/sync/messageService.ts b/hub/src/sync/messageService.ts
index c5bfd3163..02cd521a0 100644
--- a/hub/src/sync/messageService.ts
+++ b/hub/src/sync/messageService.ts
@@ -1,8 +1,49 @@
-import type { AttachmentMetadata, DecryptedMessage } from '@hapi/protocol/types'
+import type { AgentState, AgentStateCompletedRequest, AgentStateRequest, AttachmentMetadata, DecryptedMessage } from '@hapi/protocol/types'
 import type { Server } from 'socket.io'
 import type { Store } from '../store'
 import { EventPublisher } from './eventPublisher'
 
+export type FilteredPermissions = {
+    requests: Record<string, AgentStateRequest>
+    completedRequests: Record<string, AgentStateCompletedRequest>
+}
+
+/**
+ * Filter permissions by time range based on messages.
+ * Only returns permissions that were created within or after the oldest message's time.
+ */
+export function filterPermissionsByTimeRange(
+    agentState: AgentState | null | undefined,
+    messages: DecryptedMessage[]
+): FilteredPermissions {
+    if (!agentState || messages.length === 0) {
+        return { requests: {}, completedRequests: {} }
+    }
+
+    const oldestTime = Math.min(...messages.map(m => m.createdAt))
+
+    const requests: Record<string, AgentStateRequest> = {}
+    const completedRequests: Record<string, AgentStateCompletedRequest> = {}
+
+    // Filter pending requests
+    for (const [id, req] of Object.entries(agentState.requests ?? {})) {
+        const createdAt = req.createdAt ?? Date.now()
+        if (createdAt >= oldestTime) {
+            requests[id] = req
+        }
+    }
+
+    // Filter completed requests
+    for (const [id, req] of Object.entries(agentState.completedRequests ?? {})) {
+        const createdAt = req.createdAt ?? 0
+        if (createdAt >= oldestTime) {
+            completedRequests[id] = req
+        }
+    }
+
+    return { requests, completedRequests }
+}
+
 export class MessageService {
     constructor(
         private readonly store: Store,
@@ -11,7 +52,7 @@ export class MessageService {
     ) {
     }
 
-    getMessagesPage(sessionId: string, options: { limit: number; beforeSeq: number | null }): {
+    getMessagesPage(sessionId: string, options: { limit: number; beforeSeq: number | null }, agentState?: AgentState | null): {
         messages: DecryptedMessage[]
         page: {
             limit: number
@@ -19,6 +60,7 @@ export class MessageService {
             nextBeforeSeq: number | null
             hasMore: boolean
         }
+        permissions: FilteredPermissions
     } {
         const stored = this.store.messages.getMessages(sessionId, options.limit, options.beforeSeq ?? undefined)
         const messages: DecryptedMessage[] = stored.map((message) => ({
@@ -41,6 +83,9 @@ export class MessageService {
         const hasMore = nextBeforeSeq !== null
             && this.store.messages.getMessages(sessionId, 1, nextBeforeSeq).length > 0
 
+        // Filter permissions by time range
+        const permissions = filterPermissionsByTimeRange(agentState, messages)
+
         return {
             messages,
             page: {
@@ -48,7 +93,8 @@ export class MessageService {
                 beforeSeq: options.beforeSeq,
                 nextBeforeSeq,
                 hasMore
-            }
+            },
+            permissions
         }
     }
 
diff --git a/hub/src/sync/syncEngine.ts b/hub/src/sync/syncEngine.ts
index 1ab46e65f..3fdda791c 100644
--- a/hub/src/sync/syncEngine.ts
+++ b/hub/src/sync/syncEngine.ts
@@ -7,7 +7,7 @@
  * - No E2E encryption; data is stored as JSON in SQLite
  */
 
-import type { DecryptedMessage, ModelMode, PermissionMode, Session, SyncEvent } from '@hapi/protocol/types'
+import type { AgentState, DecryptedMessage, ModelMode, PermissionMode, Session, SyncEvent } from '@hapi/protocol/types'
 import type { Server } from 'socket.io'
 import type { Store } from '../store'
 import type { RpcRegistry } from '../socket/rpcRegistry'
@@ -145,7 +145,7 @@ export class SyncEngine {
         return this.machineCache.getOnlineMachinesByNamespace(namespace)
     }
 
-    getMessagesPage(sessionId: string, options: { limit: number; beforeSeq: number | null }): {
+    getMessagesPage(sessionId: string, options: { limit: number; beforeSeq: number | null }, agentState?: AgentState | null): {
         messages: DecryptedMessage[]
         page: {
             limit: number
@@ -153,8 +153,12 @@ export class SyncEngine {
             nextBeforeSeq: number | null
             hasMore: boolean
         }
+        permissions: {
+            requests: Record<string, unknown>
+            completedRequests: Record<string, unknown>
+        }
     } {
-        return this.messageService.getMessagesPage(sessionId, options)
+        return this.messageService.getMessagesPage(sessionId, options, agentState)
     }
 
     getMessagesAfter(sessionId: string, options: { afterSeq: number; limit: number }): DecryptedMessage[] {
diff --git a/hub/src/web/routes/messages.ts b/hub/src/web/routes/messages.ts
index 492298f28..8fda1cb6d 100644
--- a/hub/src/web/routes/messages.ts
+++ b/hub/src/web/routes/messages.ts
@@ -30,11 +30,12 @@ export function createMessagesRoutes(getSyncEngine: () => SyncEngine | null): Ho
             return sessionResult
         }
         const sessionId = sessionResult.sessionId
+        const agentState = sessionResult.session.agentState
 
         const parsed = querySchema.safeParse(c.req.query())
         const limit = parsed.success ? (parsed.data.limit ?? 50) : 50
         const beforeSeq = parsed.success ? (parsed.data.beforeSeq ?? null) : null
-        return c.json(engine.getMessagesPage(sessionId, { limit, beforeSeq }))
+        return c.json(engine.getMessagesPage(sessionId, { limit, beforeSeq }, agentState))
     })
 
     app.post('/sessions/:id/messages', async (c) => {
diff --git a/web/src/chat/reducer.ts b/web/src/chat/reducer.ts
index 798499c67..45046eca5 100644
--- a/web/src/chat/reducer.ts
+++ b/web/src/chat/reducer.ts
@@ -48,24 +48,12 @@ export function reduceChatBlocks(
     let hasReadyEvent = rootResult.hasReadyEvent
 
     // Only create permission-only tool cards when there is no tool call/result in the transcript.
-    // Also skip if the permission is older than the oldest message in the current view,
-    // to avoid mixing old tool cards with newer messages when paginating.
-    const oldestMessageTime = normalized.length > 0
-        ? Math.min(...normalized.map(m => m.createdAt))
-        : null
-
     for (const [id, entry] of permissionsById) {
         if (toolIdsInMessages.has(id)) continue
         if (rootResult.toolBlocksById.has(id)) continue
 
         const createdAt = entry.permission.createdAt ?? Date.now()
 
-        // Skip permissions that are older than the oldest message in the current view.
-        // These will be shown when the user loads older messages.
-        if (oldestMessageTime !== null && createdAt < oldestMessageTime) {
-            continue
-        }
-
         const block = ensureToolBlock(rootResult.blocks, rootResult.toolBlocksById, id, {
             createdAt,
             localId: null,
diff --git a/web/src/components/SessionChat.tsx b/web/src/components/SessionChat.tsx
index 3990cc295..0f7184ead 100644
--- a/web/src/components/SessionChat.tsx
+++ b/web/src/components/SessionChat.tsx
@@ -2,7 +2,7 @@ import { useCallback, useEffect, useMemo, useRef, useState } from 'react'
 import { useNavigate } from '@tanstack/react-router'
 import { AssistantRuntimeProvider } from '@assistant-ui/react'
 import type { ApiClient } from '@/api/client'
-import type { AttachmentMetadata, DecryptedMessage, ModelMode, PermissionMode, Session } from '@/types/api'
+import type { AttachmentMetadata, DecryptedMessage, FilteredPermissions, ModelMode, PermissionMode, Session } from '@/types/api'
 import type { ChatBlock, NormalizedMessage } from '@/chat/types'
 import type { Suggestion } from '@/hooks/useActiveSuggestions'
 import { normalizeDecryptedMessage } from '@/chat/normalize'
@@ -22,6 +22,7 @@ export function SessionChat(props: {
     api: ApiClient
     session: Session
     messages: DecryptedMessage[]
+    permissions: FilteredPermissions
     messagesWarning: string | null
     hasMoreMessages: boolean
     isLoadingMessages: boolean
@@ -179,9 +180,40 @@ export function SessionChat(props: {
         return normalized
     }, [props.messages])
 
+    // Build filtered agentState using permissions from message window
+    // For pending requests, always use real-time data from agentState (SSE updates)
+    // For completed requests, merge filtered API data with real-time SSE updates
+    // This ensures old tool cards are filtered out while new completions appear immediately
+    const filteredAgentState = useMemo(() => {
+        if (!props.session.agentState) return null
+
+        // Calculate oldest message time for filtering
+        const oldestMessageTime = normalizedMessages.length > 0
+            ? Math.min(...normalizedMessages.map(m => m.createdAt))
+            : null
+
+        // Get live completed requests from SSE
+        const liveCompleted = props.session.agentState.completedRequests ?? {}
+
+        // Filter live completed requests by message time range
+        const filteredLiveCompleted = oldestMessageTime === null
+            ? liveCompleted
+            : Object.fromEntries(
+                Object.entries(liveCompleted).filter(([, req]) => (req.createdAt ?? 0) >= oldestMessageTime)
+            )
+
+        return {
+            ...props.session.agentState,
+            requests: props.session.agentState.requests ?? {},
+            // Merge API-filtered permissions with filtered live completions
+            // Live completions take precedence to show real-time updates
+            completedRequests: { ...props.permissions.completedRequests, ...filteredLiveCompleted }
+        }
+    }, [props.session.agentState, props.permissions, normalizedMessages])
+
     const reduced = useMemo(
-        () => reduceChatBlocks(normalizedMessages, props.session.agentState),
-        [normalizedMessages, props.session.agentState]
+        () => reduceChatBlocks(normalizedMessages, filteredAgentState),
+        [normalizedMessages, filteredAgentState]
     )
     const reconciled = useMemo(
         () => reconcileChatBlocks(reduced.blocks, blocksByIdRef.current),
diff --git a/web/src/hooks/queries/useMessages.ts b/web/src/hooks/queries/useMessages.ts
index 237e16f87..84dfb2a2d 100644
--- a/web/src/hooks/queries/useMessages.ts
+++ b/web/src/hooks/queries/useMessages.ts
@@ -1,6 +1,6 @@
 import { useCallback, useEffect, useSyncExternalStore } from 'react'
 import type { ApiClient } from '@/api/client'
-import type { DecryptedMessage } from '@/types/api'
+import type { DecryptedMessage, FilteredPermissions } from '@/types/api'
 import {
     clearMessageWindow,
     fetchLatestMessages,
@@ -12,9 +12,12 @@ import {
     type MessageWindowState,
 } from '@/lib/message-window-store'
 
+const emptyPermissions: FilteredPermissions = { requests: {}, completedRequests: {} }
+
 const EMPTY_STATE: MessageWindowState = {
     sessionId: 'unknown',
     messages: [],
+    permissions: emptyPermissions,
     pending: [],
     pendingCount: 0,
     hasMore: false,
@@ -29,6 +32,7 @@ const EMPTY_STATE: MessageWindowState = {
 
 export function useMessages(api: ApiClient | null, sessionId: string | null): {
     messages: DecryptedMessage[]
+    permissions: FilteredPermissions
     warning: string | null
     isLoading: boolean
     isLoadingMore: boolean
@@ -98,6 +102,7 @@ export function useMessages(api: ApiClient | null, sessionId: string | null): {
 
     return {
         messages: state.messages,
+        permissions: state.permissions,
         warning: state.warning,
         isLoading: state.isLoading,
         isLoadingMore: state.isLoadingMore,
diff --git a/web/src/lib/message-window-store.ts b/web/src/lib/message-window-store.ts
index 76388b7de..82e027b7f 100644
--- a/web/src/lib/message-window-store.ts
+++ b/web/src/lib/message-window-store.ts
@@ -1,11 +1,14 @@
 import type { ApiClient } from '@/api/client'
-import type { DecryptedMessage, MessageStatus } from '@/types/api'
+import type { DecryptedMessage, FilteredPermissions, MessageStatus } from '@/types/api'
 import { normalizeDecryptedMessage } from '@/chat/normalize'
 import { mergeMessages } from '@/lib/messages'
 
+const emptyPermissions: FilteredPermissions = { requests: {}, completedRequests: {} }
+
 export type MessageWindowState = {
     sessionId: string
     messages: DecryptedMessage[]
+    permissions: FilteredPermissions
     pending: DecryptedMessage[]
     pendingCount: number
     hasMore: boolean
@@ -90,6 +93,7 @@ function createState(sessionId: string): InternalState {
     return {
         sessionId,
         messages: [],
+        permissions: emptyPermissions,
         pending: [],
         pendingCount: 0,
         pendingVisibleCount: 0,
@@ -158,6 +162,7 @@ function buildState(
     prev: InternalState,
     updates: {
         messages?: DecryptedMessage[]
+        permissions?: FilteredPermissions
         pending?: DecryptedMessage[]
         pendingOverflowCount?: number
         pendingVisibleCount?: number
@@ -170,6 +175,7 @@ function buildState(
     }
 ): InternalState {
     const messages = updates.messages ?? prev.messages
+    const permissions = updates.permissions ?? prev.permissions
     const pending = updates.pending ?? prev.pending
     const pendingOverflowCount = updates.pendingOverflowCount ?? prev.pendingOverflowCount
     const pendingOverflowVisibleCount = updates.pendingOverflowVisibleCount ?? prev.pendingOverflowVisibleCount
@@ -188,6 +194,7 @@ function buildState(
     return {
         ...prev,
         messages,
+        permissions,
         pending,
         pendingOverflowCount,
         pendingVisibleCount,
@@ -332,6 +339,7 @@ export async function fetchLatestMessages(api: ApiClient, sessionId: string): Pr
                 const trimmed = trimVisible(merged, 'append')
                 return buildState(prev, {
                     messages: trimmed,
+                    permissions: response.permissions,
                     pending: [],
                     pendingOverflowCount: 0,
                     pendingVisibleCount: 0,
@@ -343,6 +351,7 @@ export async function fetchLatestMessages(api: ApiClient, sessionId: string): Pr
             }
             const pendingResult = mergeIntoPending(prev, response.messages)
             return buildState(prev, {
+                permissions: response.permissions,
                 pending: pendingResult.pending,
                 pendingVisibleCount: pendingResult.pendingVisibleCount,
                 pendingOverflowCount: pendingResult.pendingOverflowCount,
@@ -372,8 +381,14 @@ export async function fetchOlderMessages(api: ApiClient, sessionId: string): Pro
         updateState(sessionId, (prev) => {
             const merged = mergeMessages(response.messages, prev.messages)
             const trimmed = trimVisible(merged, 'prepend')
+            // Merge permissions: combine old and new permissions
+            const mergedPermissions: FilteredPermissions = {
+                requests: { ...prev.permissions.requests, ...response.permissions.requests },
+                completedRequests: { ...prev.permissions.completedRequests, ...response.permissions.completedRequests }
+            }
             return buildState(prev, {
                 messages: trimmed,
+                permissions: mergedPermissions,
                 hasMore: response.page.hasMore,
                 isLoadingMore: false,
             })
diff --git a/web/src/lib/messages.ts b/web/src/lib/messages.ts
index cd51888e3..ac3396c48 100644
--- a/web/src/lib/messages.ts
+++ b/web/src/lib/messages.ts
@@ -97,6 +97,7 @@ export function upsertMessagesInCache(
     incoming: DecryptedMessage[],
 ): InfiniteData<MessagesResponse> {
     const mergedIncoming = mergeMessages([], incoming)
+    const emptyPermissions = { requests: {}, completedRequests: {} }
 
     if (!data || data.pages.length === 0) {
         return {
@@ -109,6 +110,7 @@ export function upsertMessagesInCache(
                         nextBeforeSeq: null,
                         hasMore: false,
                     },
+                    permissions: emptyPermissions,
                 },
             ],
             pageParams: [null],
diff --git a/web/src/router.tsx b/web/src/router.tsx
index 0dd3ad155..05f0f897f 100644
--- a/web/src/router.tsx
+++ b/web/src/router.tsx
@@ -191,6 +191,7 @@ function SessionPage() {
     } = useSession(api, sessionId)
     const {
         messages,
+        permissions: messagesPermissions,
         warning: messagesWarning,
         isLoading: messagesLoading,
         isLoadingMore: messagesLoadingMore,
@@ -298,6 +299,7 @@ function SessionPage() {
             api={api}
             session={session}
             messages={messages}
+            permissions={messagesPermissions}
             messagesWarning={messagesWarning}
             hasMoreMessages={messagesHasMore}
             isLoadingMessages={messagesLoading}
diff --git a/web/src/types/api.ts b/web/src/types/api.ts
index 278a49bf2..5e0e0df48 100644
--- a/web/src/types/api.ts
+++ b/web/src/types/api.ts
@@ -1,4 +1,6 @@
 import type {
+    AgentStateCompletedRequest,
+    AgentStateRequest,
     DecryptedMessage as ProtocolDecryptedMessage,
     Session,
     SessionSummary,
@@ -8,6 +10,8 @@ import type {
 
 export type {
     AgentState,
+    AgentStateCompletedRequest,
+    AgentStateRequest,
     AttachmentMetadata,
     ModelMode,
     PermissionMode,
@@ -61,6 +65,12 @@ export type AuthResponse = {
 
 export type SessionsResponse = { sessions: SessionSummary[] }
 export type SessionResponse = { session: Session }
+
+export type FilteredPermissions = {
+    requests: Record<string, AgentStateRequest>
+    completedRequests: Record<string, AgentStateCompletedRequest>
+}
+
 export type MessagesResponse = {
     messages: DecryptedMessage[]
     page: {
@@ -69,6 +79,7 @@ export type MessagesResponse = {
         nextBeforeSeq: number | null
         hasMore: boolean
     }
+    permissions: FilteredPermissions
 }
 
 export type MachinesResponse = { machines: Machine[] }