Reconcile extra session segments before skipping empty checkpoints

src/session/optimized-context-store.test.ts

@@ -728,6 +728,68 @@ describe("createOptimizedContextStore checkpoint", () => {
     expect(tree).not.toContain("partial.jsonl");
     expect(tree).not.toContain("untracked-junk.txt");
   });
+
+  test("commits an on-disk extra turn segment that is not in HEAD without writeTurns", async () => {
+    const dir = tempDir();
+    const store = await createOptimizedContextStore(dir);
+    await store.writeTurns([turn("a")]);
+    await store.writePrompt([turn("p0")]);
+    await store.writeMetadata(EMPTY_CHECKPOINT_METADATA);
+    const first = await store.commit({ message: "base" });
+
+    const extraTurns = segmentFileName(TURNS_FILE, 1);
+    const extraPrompt = segmentFileName("prompt.jsonl", 1);
+    fs.writeFileSync(path.join(dir, extraTurns), jsonl([turn("b")]));
+    fs.writeFileSync(path.join(dir, extraPrompt), jsonl([turn("p")]));
+
+    const crashed = await createOptimizedContextStore(dir);
+    const second = await crashed.commit({ message: "heal extra segments" });
+    expect(second.hash).not.toBe(first.hash);
+
+    const tree = await gitLsTree(dir);
+    expect(tree).toContain(extraTurns);
+    expect(tree).toContain(extraPrompt);
+  });
+
+  test("pending extra turn segment prevents empty-checkpoint skip", async () => {
+    const dir = tempDir();
+    const store = await createOptimizedContextStore(dir);
+    const turns: ConversationTurn[] = [];
+    const big = "x".repeat(20_000);
+    for (let i = 0; i < 14; i++) {
+      turns.push(turn(`${i}-${big}`));
+      await store.writeTurns([...turns]);
+    }
+    await store.writeMetadata(EMPTY_CHECKPOINT_METADATA);
+    const first = await store.commit({ message: "base" });
+
+    for (let i = 14; i < 18; i++) {
+      turns.push(turn(`${i}-${big}`));
+      await store.writeTurns([...turns]);
+    }
+    const extraTurns = segmentFileName(TURNS_FILE, 1);
+    expect(fs.existsSync(path.join(dir, extraTurns))).toBe(true);
+
+    const second = await store.commit({ message: "pending extra" });
+    expect(second.hash).not.toBe(first.hash);
+    expect(await gitLsTree(dir)).toContain(extraTurns);
+  });
+
+  test("staged compact with unchanged disk still commits instead of returning HEAD", async () => {
+    const dir = tempDir();
+    const store = await createOptimizedContextStore(dir);
+    await store.writeTurns([turn("keep-a"), turn("keep-b"), turn("drop-me")]);
+    await store.writeMetadata(EMPTY_CHECKPOINT_METADATA);
+    const first = await store.commit({ message: "published original" });
+
+    await store.writeTurns([turn("[Compacted prior context]"), turn("keep-b")]);
+    const second = await store.commit({ message: "publish compact" });
+    expect(second.hash).not.toBe(first.hash);
+    expect(turnTexts((await store.load()).turns)).toEqual([
+      "[Compacted prior context]",
+      "keep-b",
+    ]);
+  });
 });
 
 describe("createSessionStores", () => {

src/session/optimized-context-store.ts

@@ -742,28 +742,6 @@ export async function createSessionStores(
         const headBefore = stagedRewrite === null ? null : await headOid(dir);
         let extraPaths: string[] = [];
 
-        // Empty managed checkpoints must not create a new commit or stage
-        // session junk such as partial.jsonl. A staged unpublished rewrite
-        // is still unpublished on disk — skip would swallow the compact
-        // without writing it, so that path always goes through commit.
-        if (stagedRewrite === null) {
-          const managedFilepaths = [
-            ...VENDOR_COMMIT_ROOT_FILES,
-            TOOL_OUTPUT_DIR,
-            EVIDENCE_ARCHIVE_DIR,
-            ...pendingSegmentPaths,
-            ...pendingBlobFilepaths,
-          ];
-          if (!(await managedPathsDiffer(dir, managedFilepaths))) {
-            const [head] = await base.log(1);
-            if (head !== undefined) {
-              pendingBlobFilepaths.clear();
-              pendingSegmentPaths.clear();
-              return head;
-            }
-          }
-        }
-
         try {
           if (stagedRewrite !== null) {
             await writeSegmented(writeTurnsSegmented, stagedRewrite);
@@ -789,6 +767,31 @@ export async function createSessionStores(
             toAdd.push(EVIDENCE_ARCHIVE_DIR);
           }
 
+          // Empty managed checkpoints must not create a new commit or stage
+          // session junk such as partial.jsonl. Discover extra turn/prompt
+          // segments first so a crash that left them untracked cannot skip.
+          // A staged unpublished rewrite is still unpublished on disk — skip
+          // would swallow the compact without writing it.
+          if (stagedRewrite === null) {
+            const managedFilepaths = [
+              ...VENDOR_COMMIT_ROOT_FILES,
+              TOOL_OUTPUT_DIR,
+              EVIDENCE_ARCHIVE_DIR,
+              ...pendingSegmentPaths,
+              ...pendingBlobFilepaths,
+              ...toAdd,
+              ...toRemove,
+            ];
+            if (!(await managedPathsDiffer(dir, managedFilepaths))) {
+              const [head] = await base.log(1);
+              if (head !== undefined) {
+                pendingBlobFilepaths.clear();
+                pendingSegmentPaths.clear();
+                return head;
+              }
+            }
+          }
+
           const add = extraCommitPaths([...new Set(toAdd)]);
           const remove = extraCommitPaths([...new Set(toRemove)]).filter(
             (p) => !add.includes(p),