diff --git a/packages/app/src/timeline/session-stream-reducers.test.ts b/packages/app/src/timeline/session-stream-reducers.test.ts
index 6c2ce8d90..848c34982 100644
--- a/packages/app/src/timeline/session-stream-reducers.test.ts
+++ b/packages/app/src/timeline/session-stream-reducers.test.ts
@@ -69,6 +69,14 @@ function makeTimelineEvent(
   } as AgentStreamEventPayload;
 }
 
+function makeAssistantTimelineEvent(text: string, messageId?: string): AgentStreamEventPayload {
+  return {
+    type: "timeline",
+    provider: "claude",
+    item: { type: "assistant_message", text, ...(messageId ? { messageId } : {}) },
+  } as AgentStreamEventPayload;
+}
+
 function makeToolCallTimelineEvent(callId: string): AgentStreamEventPayload {
   return {
     type: "timeline",
@@ -1523,6 +1531,65 @@ describe("processAgentStreamEvents", () => {
     expect(result.sideEffects).toEqual([]);
   });
 
+  it("keeps matching assistant message ids in the live head", () => {
+    const result = processAgentStreamEvents({
+      events: [
+        makeStreamReducerEvent(makeAssistantTimelineEvent("Hel", "assistant-one"), 1),
+        makeStreamReducerEvent(makeAssistantTimelineEvent("lo", "assistant-one"), 2),
+      ],
+      currentTail: [],
+      currentHead: [],
+      currentCursor: undefined,
+      currentAgent: null,
+    });
+
+    expect(result.changedTail).toBe(false);
+    expect(result.changedHead).toBe(true);
+    expect(result.tail).toEqual([]);
+    expect(result.head).toHaveLength(1);
+    expect(result.head[0]).toMatchObject({
+      kind: "assistant_message",
+      text: "Hello",
+      messageId: "assistant-one",
+    });
+  });
+
+  it("flushes the live assistant head before starting a different assistant message id", () => {
+    const result = processAgentStreamEvents({
+      events: [
+        makeStreamReducerEvent(makeAssistantTimelineEvent("First", "assistant-one"), 1),
+        makeStreamReducerEvent(makeAssistantTimelineEvent("Second", "assistant-two"), 2),
+      ],
+      currentTail: [],
+      currentHead: [],
+      currentCursor: undefined,
+      currentAgent: null,
+    });
+
+    expect(result.changedTail).toBe(true);
+    expect(result.changedHead).toBe(true);
+    expect(getAssistantTexts(result.tail)).toEqual(["First"]);
+    expect(getAssistantTexts(result.head)).toEqual(["Second"]);
+  });
+
+  it("flushes an anonymous assistant head before starting an identified assistant message", () => {
+    const result = processAgentStreamEvents({
+      events: [
+        makeStreamReducerEvent(makeAssistantTimelineEvent("Anonymous"), 1),
+        makeStreamReducerEvent(makeAssistantTimelineEvent("Identified", "assistant-two"), 2),
+      ],
+      currentTail: [],
+      currentHead: [],
+      currentCursor: undefined,
+      currentAgent: null,
+    });
+
+    expect(result.changedTail).toBe(true);
+    expect(result.changedHead).toBe(true);
+    expect(getAssistantTexts(result.tail)).toEqual(["Anonymous"]);
+    expect(getAssistantTexts(result.head)).toEqual(["Identified"]);
+  });
+
   it("promotes completed assistant markdown blocks to tail while keeping the live block in head", () => {
     const result = processAgentStreamEvents({
       events: [
@@ -1632,6 +1699,92 @@ describe("processAgentStreamEvents", () => {
     } satisfies TimelineCursor);
   });
 
+  it("keeps Claude image tool-result output before following assistant blocks while text streams", () => {
+    const imageMarkdown =
+      "![Image](/tmp/paseo-attachments/aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa.png)";
+    const result = processAgentStreamEvents({
+      events: [
+        makeStreamReducerEvent(
+          {
+            type: "timeline",
+            provider: "claude",
+            item: {
+              type: "assistant_message",
+              text: "ABC",
+              messageId: "assistant-before",
+            },
+          } as AgentStreamEventPayload,
+          1,
+        ),
+        makeStreamReducerEvent(makeToolCallTimelineEvent("toolu_read_png"), 2),
+        makeStreamReducerEvent(
+          {
+            type: "timeline",
+            provider: "claude",
+            item: {
+              type: "tool_call",
+              callId: "toolu_read_png",
+              name: "Read",
+              status: "completed",
+              detail: {
+                type: "read",
+                filePath: "/tmp/image.png",
+              },
+              error: null,
+            },
+          } as AgentStreamEventPayload,
+          3,
+        ),
+        makeStreamReducerEvent(
+          {
+            type: "timeline",
+            provider: "claude",
+            item: {
+              type: "assistant_message",
+              text: imageMarkdown,
+            },
+          } as AgentStreamEventPayload,
+          4,
+        ),
+        makeStreamReducerEvent(
+          {
+            type: "timeline",
+            provider: "claude",
+            item: {
+              type: "assistant_message",
+              text: "D",
+              messageId: "assistant-after",
+            },
+          } as AgentStreamEventPayload,
+          5,
+        ),
+        makeStreamReducerEvent(
+          {
+            type: "timeline",
+            provider: "claude",
+            item: {
+              type: "assistant_message",
+              text: "\n\nE",
+              messageId: "assistant-after",
+            },
+          } as AgentStreamEventPayload,
+          6,
+        ),
+      ],
+      currentTail: [],
+      currentHead: [],
+      currentCursor: undefined,
+      currentAgent: null,
+    });
+
+    expect(getAssistantTexts([...result.tail, ...result.head])).toEqual([
+      "ABC",
+      imageMarkdown,
+      "D",
+      "E",
+    ]);
+  });
+
   it("returns the final optimistic lifecycle patch across a batch", () => {
     const result = processAgentStreamEvents({
       events: [
diff --git a/packages/app/src/types/stream.ts b/packages/app/src/types/stream.ts
index 67c7480d0..fb711fd2a 100644
--- a/packages/app/src/types/stream.ts
+++ b/packages/app/src/types/stream.ts
@@ -888,6 +888,13 @@ function getEventItemKind(event: AgentStreamEventPayload): StreamItem["kind"] |
   }
 }
 
+function getIncomingAssistantMessageId(event: AgentStreamEventPayload): string | undefined {
+  if (event.type !== "timeline" || event.item.type !== "assistant_message") {
+    return undefined;
+  }
+  return event.item.messageId;
+}
+
 /**
  * Finalize head items before flushing to tail.
  * Marks thoughts as "ready" since they're no longer being streamed.
@@ -939,10 +946,7 @@ function getTailAssistantToResume(params: {
   if (params.tailAssistant?.kind !== "assistant_message") {
     return null;
   }
-  const incomingMessageId =
-    params.event.type === "timeline" && params.event.item.type === "assistant_message"
-      ? params.event.item.messageId
-      : undefined;
+  const incomingMessageId = getIncomingAssistantMessageId(params.event);
   if (incomingMessageId !== undefined && params.tailAssistant.messageId !== incomingMessageId) {
     return null;
   }
@@ -1036,9 +1040,14 @@ export function flushHeadToTail(tail: StreamItem[], head: StreamItem[]): StreamI
 
 /**
  * Determine if the head should be flushed based on incoming event kind.
- * Flush when a different kind arrives or when the incoming kind is not streamable.
+ * Flush when a different streamable lane starts, including a new identified assistant message.
  */
-function shouldFlushHead(head: StreamItem[], incomingKind: StreamItem["kind"] | null): boolean {
+function shouldFlushHead(input: {
+  head: StreamItem[];
+  incomingKind: StreamItem["kind"] | null;
+  event: AgentStreamEventPayload;
+}): boolean {
+  const { head, incomingKind, event } = input;
   if (head.length === 0) {
     return false;
   }
@@ -1072,6 +1081,11 @@ function shouldFlushHead(head: StreamItem[], incomingKind: StreamItem["kind"] |
     return true;
   }
 
+  if (incomingKind === "assistant_message" && lastStreamable.kind === "assistant_message") {
+    const incomingMessageId = getIncomingAssistantMessageId(event);
+    return incomingMessageId !== undefined && lastStreamable.messageId !== incomingMessageId;
+  }
+
   return false;
 }
 
@@ -1134,7 +1148,13 @@ export function applyStreamEvent(params: {
   const incomingKind = getEventItemKind(event);
 
   // Check if we need to flush head before processing this event
-  if (shouldFlushHead(nextHead, incomingKind)) {
+  if (
+    shouldFlushHead({
+      head: nextHead,
+      incomingKind,
+      event,
+    })
+  ) {
     flushHead();
   }