diff --git a/src/infra/session-cost-usage.test.ts b/src/infra/session-cost-usage.test.ts
index 387cd6417479..f2dcd2d64a3c 100644
--- a/src/infra/session-cost-usage.test.ts
+++ b/src/infra/session-cost-usage.test.ts
@@ -2753,4 +2753,28 @@ example
       loadSessionLogs({ sessionFile, limit: Number.POSITIVE_INFINITY }),
     ).resolves.toEqual([]);
   });
+
+  it("keeps the latest logs when transcript timestamps are out of order", async () => {
+    const root = await makeSessionCostRoot("session-logs-unsorted-limit");
+    const sessionFile = path.join(root, "session.jsonl");
+    const entries = [
+      ["2026-02-12T10:03:00.000Z", "third"],
+      ["2026-02-12T10:01:00.000Z", "first"],
+      ["2026-02-12T10:04:00.000Z", "fourth"],
+      ["2026-02-12T10:02:00.000Z", "second"],
+    ].map(([timestamp, content]) => ({
+      type: "message",
+      timestamp,
+      message: { role: "user", content },
+    }));
+    await fs.writeFile(
+      sessionFile,
+      entries.map((entry) => JSON.stringify(entry)).join("\n"),
+      "utf-8",
+    );
+
+    const logs = await loadSessionLogs({ sessionFile, limit: 2 });
+
+    expect(logs?.map((log) => log.content)).toEqual(["third", "fourth"]);
+  });
 });
diff --git a/src/infra/session-cost-usage.ts b/src/infra/session-cost-usage.ts
index cd3e97ea95d5..c8f074dec0d7 100644
--- a/src/infra/session-cost-usage.ts
+++ b/src/infra/session-cost-usage.ts
@@ -2525,6 +2525,8 @@ export async function loadSessionLogs(params: {
     }
   }
   const limit = params.limit ?? 50;
+  const boundedLimit = Number.isInteger(limit);
+  const retentionLimit = limit * 2;
   const resolveCost = createUsageCostResolver(params.config);
 
   for await (const parsed of readJsonlRecords(sessionFile)) {
@@ -2656,15 +2658,25 @@ export async function loadSessionLogs(params: {
         tokens,
         cost,
       });
+      // Timestamps can arrive out of order, so keep a bounded sorted window instead
+      // of relying on transcript append order or retaining the whole file.
+      if (boundedLimit && logs.length > retentionLimit) {
+        logs.sort((a, b) => a.timestamp - b.timestamp);
+        logs.splice(0, logs.length - limit);
+      }
     } catch {
       // Ignore malformed lines
     }
   }
 
   // Sort by timestamp and limit
-  const sortedLogs = logs.toSorted((a, b) => a.timestamp - b.timestamp);
+  if (boundedLimit) {
+    logs.sort((a, b) => a.timestamp - b.timestamp);
+    return logs.length > limit ? logs.slice(-limit) : logs;
+  }
 
   // Return most recent logs
+  const sortedLogs = logs.toSorted((a, b) => a.timestamp - b.timestamp);
   if (sortedLogs.length > limit) {
     return sortedLogs.slice(-limit);
   }