diff --git a/web/src/chat/reducer.ts b/web/src/chat/reducer.ts
index 79df2c79..798499c6 100644
--- a/web/src/chat/reducer.ts
+++ b/web/src/chat/reducer.ts
@@ -48,11 +48,24 @@ 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 c0bd9ac7..3990cc29 100644
--- a/web/src/components/SessionChat.tsx
+++ b/web/src/components/SessionChat.tsx
@@ -141,12 +141,22 @@ export function SessionChat(props: {
         voice.toggleMic()
     }, [voice])
 
+    // Track session id to clear caches when it changes
+    const prevSessionIdRef = useRef<string | null>(null)
+
     useEffect(() => {
         normalizedCacheRef.current.clear()
         blocksByIdRef.current.clear()
     }, [props.session.id])
 
     const normalizedMessages: NormalizedMessage[] = useMemo(() => {
+        // Clear caches immediately when session changes (before useEffect runs)
+        if (prevSessionIdRef.current !== null && prevSessionIdRef.current !== props.session.id) {
+            normalizedCacheRef.current.clear()
+            blocksByIdRef.current.clear()
+        }
+        prevSessionIdRef.current = props.session.id
+
         const cache = normalizedCacheRef.current
         const normalized: NormalizedMessage[] = []
         const seen = new Set<string>()
diff --git a/web/src/lib/messages.ts b/web/src/lib/messages.ts
index d832624b..cd51888e 100644
--- a/web/src/lib/messages.ts
+++ b/web/src/lib/messages.ts
@@ -23,9 +23,11 @@ function isOptimisticMessage(msg: DecryptedMessage): boolean {
 function compareMessages(a: DecryptedMessage, b: DecryptedMessage): number {
     const aSeq = typeof a.seq === 'number' ? a.seq : null
     const bSeq = typeof b.seq === 'number' ? b.seq : null
+
     if (aSeq !== null && bSeq !== null && aSeq !== bSeq) {
         return aSeq - bSeq
     }
+
     if (a.createdAt !== b.createdAt) {
         return a.createdAt - b.createdAt
     }