diff --git a/hermes_cli/container_boot.py b/hermes_cli/container_boot.py
index 66f8f51766e..6013039dcb4 100644
--- a/hermes_cli/container_boot.py
+++ b/hermes_cli/container_boot.py
@@ -229,12 +229,32 @@ def _write_reconcile_log(
     up". Keeping a separate log file (vs. mixing into agent.log) lets
     troubleshooters grep for "profile=foo" without wading through
     unrelated activity.
+
+    Size-bounded: when the file exceeds ``_LOG_ROTATE_BYTES``
+    (defaults to 256 KiB ≈ 3000 reconcile lines), the current file
+    is renamed to ``container-boot.log.1`` (replacing any previous
+    rotation) before the new entries are appended. This gives long-
+    lived containers a soft cap of ~512 KiB across the two files
+    without pulling in logrotate or s6-log machinery just for this
+    one append-only file (PR #30136 review item O3).
     """
     import time
     log_dir = hermes_home / "logs"
     log_dir.mkdir(parents=True, exist_ok=True)
+    log_path = log_dir / "container-boot.log"
+
+    # Rotate before opening to append, so the new entries always land
+    # in a fresh file when we crossed the threshold last time.
+    try:
+        if log_path.exists() and log_path.stat().st_size >= _LOG_ROTATE_BYTES:
+            log_path.replace(log_dir / "container-boot.log.1")
+    except OSError as exc:
+        # Rotation failure is non-fatal — keep appending to the
+        # existing file rather than losing the entry entirely.
+        log.warning("could not rotate %s: %s", log_path, exc)
+
     ts = time.strftime("%Y-%m-%dT%H:%M:%S%z")
-    with (log_dir / "container-boot.log").open("a", encoding="utf-8") as f:
+    with log_path.open("a", encoding="utf-8") as f:
         for a in actions:
             f.write(
                 f"{ts} profile={a.profile} prior_state={a.prior_state} "
@@ -242,6 +262,14 @@ def _write_reconcile_log(
             )
 
 
+# 256 KiB soft cap on container-boot.log; rotated to .1 when crossed.
+# At ~80 B per reconcile-action line this is ~3000 lines, or about a
+# year of daily reboots on a 5-profile container. Two files = ~512 KiB
+# worst case. Tuned for visibility (small enough to grep / cat without
+# scrolling forever) more than space (the persistent volume has GB).
+_LOG_ROTATE_BYTES = 256 * 1024
+
+
 def main() -> int:
     """Entry point invoked from /etc/cont-init.d/02-reconcile-profiles."""
     hermes_home = Path(os.environ.get("HERMES_HOME", "/opt/data"))
diff --git a/tests/hermes_cli/test_container_boot.py b/tests/hermes_cli/test_container_boot.py
index 8272c090448..2f41f4f8e0f 100644
--- a/tests/hermes_cli/test_container_boot.py
+++ b/tests/hermes_cli/test_container_boot.py
@@ -223,6 +223,88 @@ def test_reconcile_log_is_written(tmp_path: Path) -> None:
     assert "action=registered" in log
 
 
+def test_reconcile_log_rotates_when_size_exceeded(
+    tmp_path: Path,
+    monkeypatch: pytest.MonkeyPatch,
+) -> None:
+    """When container-boot.log exceeds _LOG_ROTATE_BYTES, the existing
+    file is rotated to .1 before the new entries are appended."""
+    from hermes_cli import container_boot
+
+    # Tighten the threshold so we don't have to write 256 KiB.
+    monkeypatch.setattr(container_boot, "_LOG_ROTATE_BYTES", 200)
+
+    log_path = tmp_path / "logs" / "container-boot.log"
+    log_path.parent.mkdir()
+    log_path.write_text("X" * 300)  # already over the threshold
+
+    scandir = tmp_path / "run-service"; scandir.mkdir()
+    _make_profile(tmp_path, "coder", state="running")
+
+    reconcile_profile_gateways(
+        hermes_home=tmp_path, scandir=scandir, dry_run=False,
+    )
+
+    rotated = tmp_path / "logs" / "container-boot.log.1"
+    assert rotated.exists(), "expected previous log to be rotated to .1"
+    assert rotated.read_text().startswith("X" * 300)
+    # The new entries land in a fresh container-boot.log (no leftover Xs).
+    new_contents = log_path.read_text()
+    assert "X" not in new_contents
+    assert "profile=coder" in new_contents
+
+
+def test_reconcile_log_does_not_rotate_below_threshold(
+    tmp_path: Path,
+    monkeypatch: pytest.MonkeyPatch,
+) -> None:
+    """A small existing log is appended to in place; no .1 is created."""
+    from hermes_cli import container_boot
+    monkeypatch.setattr(container_boot, "_LOG_ROTATE_BYTES", 10_000_000)
+
+    log_path = tmp_path / "logs" / "container-boot.log"
+    log_path.parent.mkdir()
+    log_path.write_text("previous entry\n")
+
+    scandir = tmp_path / "run-service"; scandir.mkdir()
+    _make_profile(tmp_path, "coder", state="running")
+
+    reconcile_profile_gateways(
+        hermes_home=tmp_path, scandir=scandir, dry_run=False,
+    )
+
+    assert not (tmp_path / "logs" / "container-boot.log.1").exists()
+    contents = log_path.read_text()
+    assert contents.startswith("previous entry\n")
+    assert "profile=coder" in contents
+
+
+def test_reconcile_log_rotation_overwrites_existing_dot1(
+    tmp_path: Path,
+    monkeypatch: pytest.MonkeyPatch,
+) -> None:
+    """Rotating again replaces the prior .1 — we keep at most one
+    rotated file (soft cap of ~2 × threshold)."""
+    from hermes_cli import container_boot
+    monkeypatch.setattr(container_boot, "_LOG_ROTATE_BYTES", 200)
+
+    log_dir = tmp_path / "logs"; log_dir.mkdir()
+    (log_dir / "container-boot.log.1").write_text("OLD ROTATION")
+    (log_dir / "container-boot.log").write_text("Y" * 300)
+
+    scandir = tmp_path / "run-service"; scandir.mkdir()
+    _make_profile(tmp_path, "coder", state="running")
+
+    reconcile_profile_gateways(
+        hermes_home=tmp_path, scandir=scandir, dry_run=False,
+    )
+
+    # .1 now contains the previous .log (Ys), not OLD ROTATION.
+    rotated = (log_dir / "container-boot.log.1").read_text()
+    assert "OLD ROTATION" not in rotated
+    assert rotated.startswith("Y" * 300)
+
+
 def test_dry_run_makes_no_filesystem_changes(tmp_path: Path) -> None:
     scandir = tmp_path / "run-service"; scandir.mkdir()
     profile = _make_profile(tmp_path, "coder", state="running", with_pid=True)