@@ -43,11 +43,13 @@
 from dstack._internal.core.models.volumes import InstanceMountPoint, Volume, VolumeMountPoint
 from dstack._internal.server import settings as server_settings
 from dstack._internal.server.background.pipeline_tasks.base import (
+    NOW_PLACEHOLDER,
     Fetcher,
     Heartbeater,
     ItemUpdateMap,
     Pipeline,
     PipelineItem,
+    UpdateMapDateTime,
     Worker,
     log_lock_token_changed_after_processing,
     log_lock_token_mismatch,
@@ -146,6 +148,12 @@
 JOB_DISCONNECTED_RETRY_TIMEOUT = timedelta(minutes=2)
 """`The minimum time before terminating active job in case of connectivity issues."""
 
+MAX_DURATION_ENFORCEMENT_GRACE = timedelta(minutes=2)
+"""How long the server waits past `max_duration` before terminating the job itself.
+The runner enforces `max_duration` too and does it gracefully, so it normally stops the job
+well within the grace period. The server only steps in when the runner failed to.
+"""
+
 
 @dataclass
 class JobRunningPipelineItem(PipelineItem):
@@ -380,6 +388,7 @@ class _JobUpdateMap(ItemUpdateMap, total=False):
     job_provisioning_data: Optional[str]
     job_runtime_data: Optional[str]
     runner_timestamp: Optional[int]
+    running_at: UpdateMapDateTime
     disconnected_at: Optional[datetime]
     inactivity_secs: Optional[int]
     exit_status: Optional[int]
@@ -1045,6 +1054,10 @@ async def _process_running_status(
         fmt(context.job_model),
         context.job_submission.age,
     )
+    # Checked before pulling the runner: the runner may be stuck or unreachable, and that is
+    # exactly when server-side enforcement is needed.
+    if _terminate_if_max_duration_exceeded(context, result):
+        return
     try:
         process_running_result = await run_async(
             _process_running,
@@ -1808,6 +1821,48 @@ def _terminate_if_inactivity_duration_exceeded(
         )
 
 
+def _terminate_if_max_duration_exceeded(
+    context: _ProcessContext,
+    result: _ProcessResult,
+) -> bool:
+    """
+    Terminates the job if it has been running longer than `max_duration` plus a grace period.
+
+    A backstop for the runner, which enforces `max_duration` itself and does it gracefully.
+    The server steps in only when the runner failed to stop the job -- e.g. the workload
+    survived the termination signals and the runner never reported the timeout.
+
+    Returns `True` if the job was terminated.
+    """
+    job_model = context.job_model
+    max_duration = context.job.job_spec.max_duration
+    if max_duration is None:
+        return False
+    if job_model.running_at is None:
+        # Jobs that started running before the server was upgraded have no reference point.
+        # They are still enforced by the runner.
+        return False
+    deadline = (
+        job_model.running_at + timedelta(seconds=max_duration) + MAX_DURATION_ENFORCEMENT_GRACE
+    )
+    if get_current_datetime() < deadline:
+        return False
+    logger.warning(
+        "%s: max duration exceeded and the runner did not stop the job, terminating",
+        fmt(job_model),
+    )
+    _terminate_job(
+        job_model=job_model,
+        job_update_map=result.job_update_map,
+        termination_reason=JobTerminationReason.MAX_DURATION_EXCEEDED,
+        termination_reason_message=(
+            f"The job exceeded the max_duration of {max_duration} seconds"
+            " and did not stop on its own"
+        ),
+    )
+    return True
+
+
 def _should_terminate_job_due_to_disconnect(disconnected_at: Optional[datetime]) -> bool:
     if disconnected_at is None:
         return False
@@ -2088,6 +2143,10 @@ def _set_job_update_status(
 ) -> None:
     if job_update_map.get("status", job_model.status) != new_status:
         job_update_map["status"] = new_status
+        if new_status == JobStatus.RUNNING:
+            # Stamped here rather than at the call site so that `running_at` cannot drift from
+            # `status`: it is the reference point for server-side `max_duration` enforcement.
+            job_update_map["running_at"] = NOW_PLACEHOLDER
 
 
 def _set_job_status(job_model: JobModel, result: _ProcessResult, new_status: JobStatus) -> None:
 
@@ -0,0 +1,30 @@
+"""Add JobModel.running_at
+
+Revision ID: 652af7a3c9c9
+Revises: 620892d149b5
+Create Date: 2026-09-08 10:02:00.000000
+
+"""
+
+import sqlalchemy as sa
+from alembic import op
+
+import dstack._internal.server.models
+
+# revision identifiers, used by Alembic.
+revision = "652af7a3c9c9"
+down_revision = "620892d149b5"
+branch_labels = None
+depends_on = None
+
+
+def upgrade() -> None:
+    with op.batch_alter_table("jobs", schema=None) as batch_op:
+        batch_op.add_column(
+            sa.Column("running_at", dstack._internal.server.models.NaiveDateTime(), nullable=True)
+        )
+
+
+def downgrade() -> None:
+    with op.batch_alter_table("jobs", schema=None) as batch_op:
+        batch_op.drop_column("running_at")
@@ -535,6 +535,12 @@ class JobModel(PipelineModelMixin, BaseModel):
     job_name: Mapped[str] = mapped_column(String(100))
     submission_num: Mapped[int] = mapped_column(Integer)
     submitted_at: Mapped[datetime] = mapped_column(NaiveDateTime)
+    running_at: Mapped[Optional[datetime]] = mapped_column(NaiveDateTime)
+    """`running_at` stores when the job entered the `RUNNING` status, that is, when the workload
+    started, excluding provisioning and pulling. It is the reference point for server-side
+    `max_duration` enforcement. `None` for jobs that never started running and for jobs that were
+    already running before the server was upgraded.
+    """
     last_processed_at: Mapped[datetime] = mapped_column(NaiveDateTime)
     skip_min_processing_interval: Mapped[bool] = mapped_column(
         Boolean, default=False, server_default=false()
 
@@ -432,6 +432,7 @@ async def create_job(
     submission_num: int = 0,
     status: JobStatus = JobStatus.SUBMITTED,
     submitted_at: datetime = datetime(2023, 1, 2, 3, 4, tzinfo=timezone.utc),
+    running_at: Optional[datetime] = None,
     last_processed_at: datetime = datetime(2023, 1, 2, 3, 4, tzinfo=timezone.utc),
     termination_reason: Optional[JobTerminationReason] = None,
     job_provisioning_data: Optional[JobProvisioningData] = None,
@@ -475,6 +476,7 @@ async def create_job(
         deployment_num=deployment_num,
         submission_num=submission_num,
         submitted_at=submitted_at,
+        running_at=running_at,
         last_processed_at=last_processed_at,
         status=status,
         termination_reason=termination_reason,
 
@@ -26,7 +26,7 @@
 from dstack._internal.core.models.duration import Duration
 from dstack._internal.core.models.gateways import GatewayReplicaStatus, GatewayStatus
 from dstack._internal.core.models.instances import InstanceStatus
-from dstack._internal.core.models.profiles import StartupOrder, UtilizationPolicy
+from dstack._internal.core.models.profiles import Profile, StartupOrder, UtilizationPolicy
 from dstack._internal.core.models.runs import (
     ClusterInfo,
     ImagePullProgress,
@@ -44,6 +44,7 @@
 from dstack._internal.server import settings as server_settings
 from dstack._internal.server.background.pipeline_tasks.jobs_running import (
     JOB_DISCONNECTED_RETRY_TIMEOUT,
+    MAX_DURATION_ENFORCEMENT_GRACE,
     ROUTER_PROVISIONING_WAIT_TIMEOUT_SECONDS,
     JobRunningFetcher,
     JobRunningPipeline,
@@ -1752,6 +1753,128 @@ async def test_inactivity_duration(
         assert job.termination_reason == expected_termination_reason
         assert job.inactivity_secs == expected_inactivity_secs
 
+    @pytest.mark.parametrize(
+        (
+            "max_duration",
+            "running_for",
+            "stamp_running_at",
+            "expected_status",
+            "expected_termination_reason",
+            "expect_pull",
+        ),
+        [
+            pytest.param(
+                600,
+                timedelta(seconds=600),
+                True,
+                JobStatus.RUNNING,
+                None,
+                True,
+                id="deadline-reached-but-runner-still-within-grace",
+            ),
+            pytest.param(
+                600,
+                timedelta(seconds=600) + MAX_DURATION_ENFORCEMENT_GRACE - timedelta(seconds=1),
+                True,
+                JobStatus.RUNNING,
+                None,
+                True,
+                id="grace-not-elapsed",
+            ),
+            pytest.param(
+                600,
+                timedelta(seconds=600) + MAX_DURATION_ENFORCEMENT_GRACE,
+                True,
+                JobStatus.TERMINATING,
+                JobTerminationReason.MAX_DURATION_EXCEEDED,
+                False,
+                id="grace-elapsed",
+            ),
+            pytest.param(
+                600,
+                timedelta(days=1),
+                False,
+                JobStatus.RUNNING,
+                None,
+                True,
+                id="job-started-before-upgrade",
+            ),
+            pytest.param(
+                "off",
+                timedelta(days=1),
+                True,
+                JobStatus.RUNNING,
+                None,
+                True,
+                id="max-duration-off",
+            ),
+        ],
+    )
+    async def test_max_duration_enforced_by_server(
+        self,
+        test_db,
+        session: AsyncSession,
+        worker: JobRunningWorker,
+        max_duration,
+        running_for: timedelta,
+        stamp_running_at: bool,
+        expected_status: JobStatus,
+        expected_termination_reason: Optional[JobTerminationReason],
+        expect_pull: bool,
+    ) -> None:
+        now = datetime(2023, 1, 2, 5, 0, tzinfo=timezone.utc)
+        project = await create_project(session=session)
+        user = await create_user(session=session)
+        repo = await create_repo(session=session, project_id=project.id)
+        run = await create_run(
+            session=session,
+            project=project,
+            repo=repo,
+            user=user,
+            status=RunStatus.RUNNING,
+            run_name="test-run",
+            run_spec=get_run_spec(
+                run_name="test-run",
+                repo_id=repo.name,
+                profile=Profile(name="default", max_duration=max_duration),
+            ),
+        )
+        instance = await create_instance(
+            session=session,
+            project=project,
+            status=InstanceStatus.BUSY,
+        )
+        job = await create_job(
+            session=session,
+            run=run,
+            status=JobStatus.RUNNING,
+            running_at=(now - running_for) if stamp_running_at else None,
+            job_provisioning_data=get_job_provisioning_data(),
+            instance=instance,
+            instance_assigned=True,
+        )
+        with (
+            patch("dstack._internal.server.services.runner.pool.SSHTunnel"),
+            patch(
+                "dstack._internal.server.services.runner.client.RunnerClient.from_address"
+            ) as runner_client_cls,
+            freeze_time(now),
+        ):
+            runner_client_mock = runner_client_cls.return_value
+            runner_client_mock.pull.return_value = PullResponse(
+                job_states=[],
+                job_logs=[],
+                runner_logs=[],
+                last_updated=0,
+                no_connections_secs=0,
+            )
+            await _process_job(session, worker, job)
+            assert runner_client_mock.pull.called == expect_pull
+
+        await session.refresh(job)
+        assert job.status == expected_status
+        assert job.termination_reason == expected_termination_reason
+
     @pytest.mark.parametrize(
         ["samples", "expected_status"],
         [