diff --git a/apps/web/src/composables/api/useChat.content.ts b/apps/web/src/composables/api/useChat.content.ts
index fbc6b422..72ab3044 100644
--- a/apps/web/src/composables/api/useChat.content.ts
+++ b/apps/web/src/composables/api/useChat.content.ts
@@ -1,6 +1,8 @@
 import type { Message } from './useChat.types'
 
 const yamlHeaderRe = /^---\n[\s\S]*?\n---\n?/
+const agentTagsRe = /<(attachments|reactions|speech)>[\s\S]*?<\/\1>/g
+const collapsedNewlinesRe = /\n{3,}/g
 
 export function extractToolCalls(
   message: Message,
@@ -92,6 +94,8 @@ export function extractMessageText(message: Message): string {
 
   if (message.role === 'user') {
     text = stripYAMLHeader(text)
+  } else {
+    text = stripAgentTags(text)
   }
   return text
 }
@@ -100,6 +104,10 @@ export function stripYAMLHeader(text: string): string {
   return text.replace(yamlHeaderRe, '').trim()
 }
 
+export function stripAgentTags(text: string): string {
+  return text.replace(agentTagsRe, '').replace(collapsedNewlinesRe, '\n\n').trim()
+}
+
 export function extractTextFromContent(content: unknown): string {
   if (typeof content === 'string') return content.trim()
 
diff --git a/apps/web/src/store/chat-list.ts b/apps/web/src/store/chat-list.ts
index 8d020b54..c5f8aa59 100644
--- a/apps/web/src/store/chat-list.ts
+++ b/apps/web/src/store/chat-list.ts
@@ -278,6 +278,7 @@ export const useChatStore = defineStore('chat', () => {
             pendingAssistant.blocks.push(block)
             if (tc.id) pendingToolCallMap.set(tc.id, block)
           }
+          pendingAssistant.blocks.push(...buildAssetBlocks(raw))
           continue
         }
 
@@ -286,6 +287,7 @@ export const useChatStore = defineStore('chat', () => {
             pendingAssistant.blocks.push({ type: 'thinking', content: r, done: true })
           }
           pendingAssistant.blocks.push({ type: 'text', content: text })
+          pendingAssistant.blocks.push(...buildAssetBlocks(raw))
           flushPending()
           continue
         }
diff --git a/internal/agent/tags.go b/internal/agent/tags.go
index df26cae2..45ebd8df 100644
--- a/internal/agent/tags.go
+++ b/internal/agent/tags.go
@@ -107,6 +107,13 @@ func SpeechResolver() TagResolver {
 	}
 }
 
+// StripAgentTags removes all default agent tag blocks (<attachments>, <reactions>, <speech>)
+// from text, returning only the visible content.
+func StripAgentTags(text string) string {
+	cleaned, _ := ExtractTagsFromText(text, DefaultTagResolvers())
+	return cleaned
+}
+
 // ExtractTagsFromText extracts and removes all tag blocks from a complete string.
 func ExtractTagsFromText(text string, resolvers []TagResolver) (string, []TagEvent) {
 	var events []TagEvent
diff --git a/internal/conversation/flow/assistant_output.go b/internal/conversation/flow/assistant_output.go
index cce974d2..942ef675 100644
--- a/internal/conversation/flow/assistant_output.go
+++ b/internal/conversation/flow/assistant_output.go
@@ -3,6 +3,7 @@ package flow
 import (
 	"strings"
 
+	"github.com/memohai/memoh/internal/agent"
 	"github.com/memohai/memoh/internal/conversation"
 )
 
@@ -28,6 +29,7 @@ func ExtractAssistantOutputs(messages []conversation.ModelMessage) []conversatio
 		if content == "" && len(parts) == 0 {
 			continue
 		}
+		content = agent.StripAgentTags(content)
 		outputs = append(outputs, conversation.AssistantOutput{Content: content, Parts: parts})
 	}
 	return outputs
diff --git a/internal/conversation/flow/resolver_store.go b/internal/conversation/flow/resolver_store.go
index 12067a54..cf370a1a 100644
--- a/internal/conversation/flow/resolver_store.go
+++ b/internal/conversation/flow/resolver_store.go
@@ -200,14 +200,23 @@ func (r *Resolver) resolvePersistSenderIDs(ctx context.Context, req conversation
 }
 
 // LinkOutboundAssets links bot-generated assets to the latest assistant
-// message for the given bot. Used by the WebSocket path where attachment
-// ingestion happens after message persistence.
-func (r *Resolver) LinkOutboundAssets(ctx context.Context, botID string, assets []messagepkg.AssetRef) {
+// message. When sessionID is provided, the search is scoped to that session;
+// otherwise it falls back to a bot-wide search.
+// Used by the WebSocket path where attachment ingestion happens after message
+// persistence.
+func (r *Resolver) LinkOutboundAssets(ctx context.Context, botID, sessionID string, assets []messagepkg.AssetRef) {
 	if r.messageService == nil || len(assets) == 0 || strings.TrimSpace(botID) == "" {
 		return
 	}
-	// ListLatest returns messages in DESC order (newest first).
-	msgs, err := r.messageService.ListLatest(ctx, botID, 5)
+	var (
+		msgs []messagepkg.Message
+		err  error
+	)
+	if strings.TrimSpace(sessionID) != "" {
+		msgs, err = r.messageService.ListLatestBySession(ctx, sessionID, 5)
+	} else {
+		msgs, err = r.messageService.ListLatest(ctx, botID, 5)
+	}
 	if err != nil {
 		r.logger.Warn("LinkOutboundAssets: list latest failed", slog.Any("error", err))
 		return
diff --git a/internal/handlers/local_channel.go b/internal/handlers/local_channel.go
index 20e52b3d..a1c3559c 100644
--- a/internal/handlers/local_channel.go
+++ b/internal/handlers/local_channel.go
@@ -415,6 +415,7 @@ func (h *LocalChannelHandler) HandleWebSocket(c echo.Context) error {
 			activeCancel = streamCancel
 			eventCh := make(chan flow.WSStreamEvent, 64)
 
+			sessionID := strings.TrimSpace(msg.SessionID)
 			var (
 				outboundAssetMu   sync.Mutex
 				outboundAssetRefs []messagepkg.AssetRef
@@ -426,7 +427,7 @@ func (h *LocalChannelHandler) HandleWebSocket(c echo.Context) error {
 				req := conversation.ChatRequest{
 					BotID:                   botID,
 					ChatID:                  botID,
-					SessionID:               strings.TrimSpace(msg.SessionID),
+					SessionID:               sessionID,
 					Token:                   bearerToken,
 					UserID:                  channelIdentityID,
 					SourceChannelIdentityID: channelIdentityID,
@@ -462,7 +463,7 @@ func (h *LocalChannelHandler) HandleWebSocket(c echo.Context) error {
 				refs := outboundAssetRefs
 				outboundAssetMu.Unlock()
 				if len(refs) > 0 {
-					h.resolver.LinkOutboundAssets(context.WithoutCancel(ctx), botID, refs)
+					h.resolver.LinkOutboundAssets(context.WithoutCancel(ctx), botID, sessionID, refs)
 				}
 			}()