4 files changed, 86 insertions, 2 deletions

diff --git a/packages/conversation-store/src/reconcile.test.ts b/packages/conversation-store/src/reconcile.test.ts
index b1926e9..25b47d5 100644
--- a/packages/conversation-store/src/reconcile.test.ts
+++ b/packages/conversation-store/src/reconcile.test.ts
@@ -417,4 +417,18 @@ describe("reconcile", () => {
     expect(report.repairedCount).toBe(1);
     expect(report.repairedToolCallIds).toEqual(["call_orph"]);
   });
+
+  it("reconcile preserves a thinking-only assistant message", () => {
+    // Regression: an assistant message with only a thinking chunk (no text,
+    // no tool-call) was being dropped by the hasContent check. Thinking IS
+    // valid content — the model's reasoning must survive a load/reconcile
+    // cycle so it appears in the conversation history.
+    const messages: ChatMessage[] = [
+      { role: "user", chunks: [{ type: "text", text: "hello" }] },
+      { role: "assistant", chunks: [{ type: "thinking", text: "just thinking..." }] },
+    ];
+    const { messages: result, report } = reconcileWithReport(messages);
+    expect(result).toEqual(messages);
+    expect(report.droppedEmptyMessages).toBe(0);
+  });
 });
diff --git a/packages/conversation-store/src/reconcile.ts b/packages/conversation-store/src/reconcile.ts
index 9023415..2d2b68d 100644
--- a/packages/conversation-store/src/reconcile.ts
+++ b/packages/conversation-store/src/reconcile.ts
@@ -46,7 +46,7 @@ export function reconcileWithReport(messages: readonly ChatMessage[]): Reconcile
   for (const msg of stripped) {
     if (msg.role === "assistant") {
       const hasContent = msg.chunks.some(
-        (chunk) => chunk.type === "text" || chunk.type === "tool-call",
+        (chunk) => chunk.type === "text" || chunk.type === "tool-call" || chunk.type === "thinking",
       );
       if (!hasContent) {
         droppedEmptyMessages++;
diff --git a/packages/conversation-store/src/store.test.ts b/packages/conversation-store/src/store.test.ts
index 6b12d0a..d336e0e 100644
--- a/packages/conversation-store/src/store.test.ts
+++ b/packages/conversation-store/src/store.test.ts
@@ -143,6 +143,68 @@ describe("ConversationStore", () => {
     expect(result).toEqual([...turn1, ...turn2]);
   });
 
+  it("preserves message boundaries across single-message appends (orchestrator pattern)", async () => {
+    // Regression: the orchestrator persists messages one at a time —
+    // append([user]) at turn start, then append([assistant]) or
+    // append([assistant, ...toolResults]) via onStepComplete. Since each
+    // append() call assigns msgIdx starting at 0, single-message appends all
+    // share msgIdx=0. load() must split on role changes too, not just msgIdx,
+    // or messages from different turns collapse into one.
+    const store = createConversationStore(storage);
+    const user1: ChatMessage = { role: "user", chunks: [{ type: "text", text: "hello" }] };
+    const asst1: ChatMessage = {
+      role: "assistant",
+      chunks: [
+        { type: "thinking", text: "greeting" },
+        { type: "text", text: "Hi!" },
+      ],
+    };
+    const user2: ChatMessage = { role: "user", chunks: [{ type: "text", text: "read a file" }] };
+    const asst2: ChatMessage = {
+      role: "assistant",
+      chunks: [{ type: "text", text: "Sure." }],
+    };
+    const user3: ChatMessage = { role: "user", chunks: [{ type: "text", text: "thanks" }] };
+
+    // Each message appended individually — the real orchestrator pattern.
+    await store.append("conv1", [user1]);
+    await store.append("conv1", [asst1]);
+    await store.append("conv1", [user2]);
+    await store.append("conv1", [asst2]);
+    await store.append("conv1", [user3]);
+
+    const result = await store.load("conv1");
+    expect(result).toEqual([user1, asst1, user2, asst2, user3]);
+  });
+
+  it("preserves message boundaries with single-message appends + multi-message step (tool calls)", async () => {
+    // Regression: the full orchestrator pattern including tool calls.
+    // Turn: append([user]) → step: append([assistant{thinking,text,tool-call}, toolResult])
+    // All single-message appends get msgIdx=0; the multi-message step gets 0,1.
+    const store = createConversationStore(storage);
+    const user: ChatMessage = { role: "user", chunks: [{ type: "text", text: "do it" }] };
+    const asst: ChatMessage = {
+      role: "assistant",
+      chunks: [
+        { type: "thinking", text: "calling a tool" },
+        { type: "text", text: "ok" },
+        { type: "tool-call", toolCallId: "c1", toolName: "t", input: {} },
+      ],
+    };
+    const toolResult: ChatMessage = {
+      role: "tool",
+      chunks: [
+        { type: "tool-result", toolCallId: "c1", toolName: "t", content: "done", isError: false },
+      ],
+    };
+
+    await store.append("conv1", [user]);
+    await store.append("conv1", [asst, toolResult]);
+
+    const result = await store.load("conv1");
+    expect(result).toEqual([user, asst, toolResult]);
+  });
+
   it("preserves message ordering", async () => {
     const store = createConversationStore(storage);
     const messages: ChatMessage[] = [];
diff --git a/packages/conversation-store/src/store.ts b/packages/conversation-store/src/store.ts
index ed39d8e..41df92f 100644
--- a/packages/conversation-store/src/store.ts
+++ b/packages/conversation-store/src/store.ts
@@ -681,7 +681,15 @@ export function createConversationStore(
           continue;
         }
 
-        if (entry.msgIdx !== currentMsgIdx) {
+        // A message boundary is detected when EITHER the msgIdx changes OR the
+        // role changes. The msgIdx alone is insufficient because append() assigns
+        // it as a LOCAL index (reset to 0 for each call) — so consecutive
+        // single-message appends (e.g. the orchestrator's per-step persistence:
+        // append([user]) then append([assistant]) then append([user])...) all
+        // share msgIdx=0 and would collapse into one message without the role
+        // check. The role check restores correct boundaries for the common
+        // alternating user/assistant/tool pattern.
+        if (entry.msgIdx !== currentMsgIdx || entry.role !== currentRole) {
           if (currentMsgIdx >= 0 && currentRole !== undefined) {
             messages.push({ role: currentRole, chunks: currentChunks });
           }