diff --git a/internal/engine/schedule_status.go b/internal/engine/schedule_status.go
index dac4667..84c3ff8 100644
--- a/internal/engine/schedule_status.go
+++ b/internal/engine/schedule_status.go
@@ -48,6 +48,8 @@ const skipStreakIssue = 3
 type scheduleUnitObservation struct {
 	loadState   string
 	activeState string
+	result      string
+	exitStatus  int
 	release     string
 	startedAt   string
 	attempt     string
@@ -72,7 +74,9 @@ func (e *Engine) scheduleStatuses(ctx context.Context) ([]StatusSchedule, error)
 		unit := e.names().ScheduledJobUnit(job.Name)
 		commands = append(commands,
 			"printf '%s\\n' "+q("@@"+job.Name+":service"),
-			"systemctl show "+q(unit+".service")+" --no-pager --property=LoadState --property=ActiveState",
+			// Result and ExecMainStatus are the only evidence a host still
+			// running pre-record units has. See the fallback below.
+			"systemctl show "+q(unit+".service")+" --no-pager --property=LoadState --property=ActiveState --property=Result --property=ExecMainStatus",
 			"printf '%s\\n' "+q("@@"+job.Name+":timer"),
 			"systemctl show "+q(unit+".timer")+" --no-pager --property=LoadState --property=ActiveState --property=NextElapseUSecRealtime",
 			"printf '%s\\n' "+q("@@"+job.Name+":run"),
@@ -104,8 +108,10 @@ func (e *Engine) scheduleStatuses(ctx context.Context) ([]StatusSchedule, error)
 		if observed[name] == nil {
 			observed[name] = map[string]scheduleUnitObservation{}
 		}
+		exit, _ := strconv.Atoi(values["ExecMainStatus"])
 		observed[name][kind] = scheduleUnitObservation{
 			loadState: values["LoadState"], activeState: values["ActiveState"],
+			result: values["Result"], exitStatus: exit,
 			release: values["release"], startedAt: values["started_at"], attempt: values["attempt"],
 			next:    values["NextElapseUSecRealtime"],
 			history: parseScheduleRunRecords(strings.Join(raw, "\n"), name),
@@ -213,6 +219,16 @@ func (e *Engine) scheduleStatuses(ctx context.Context) ([]StatusSchedule, error)
 			}
 			status.Issues = append(status.Issues, issue)
 		}
+		// No records at all means the host is still running units written
+		// before this runner: they do not write records, so the only thing
+		// that knows how the last run ended is systemd. Upgrading `ob` must
+		// not turn a failing job silent, and the issue says what closes the
+		// gap.
+		if len(records) == 0 && service.result != "" && service.result != "success" {
+			status.Issues = append(status.Issues, fmt.Sprintf(
+				"last run failed: %s (exit %d); no run record — run `ob schedule apply` so runs are recorded",
+				service.result, service.exitStatus))
+		}
 		if status.ConsecutiveSkips >= skipStreakIssue {
 			status.Issues = append(status.Issues, fmt.Sprintf("skipped %d firings in a row: %s", status.ConsecutiveSkips, status.LastReason))
 		}
diff --git a/internal/engine/schedule_test.go b/internal/engine/schedule_test.go
index 82be9a1..3f0aeca 100644
--- a/internal/engine/schedule_test.go
+++ b/internal/engine/schedule_test.go
@@ -1604,3 +1604,82 @@ func TestScheduleSkipMarkerIsNamedIdenticallyOnBothSides(t *testing.T) {
 		t.Fatalf("runner names the note %q and the notifier %q", inRunner, inNotifier)
 	}
 }
+
+// Upgrading ob must not make a failing job go quiet. A host still running
+// units written before this runner records nothing, so systemd's own result
+// is the only evidence there is, and status has to use it.
+func TestScheduleStatusFallsBackToSystemdWhenNoRecordsExist(t *testing.T) {
+	cfg := testConfig()
+	cfg.Workloads["nightly"] = app.Workload{
+		Role: app.RoleJob, When: "manual", DataEffect: "none",
+		Schedule: &app.JobSchedule{Cron: "0 2 * * *", Timezone: "UTC", Timeout: "1h", CatchUp: true},
+	}
+	f := &transport.Fake{Dynamic: func(cmd string) (transport.Result, bool) {
+		if strings.Contains(cmd, "systemctl show") {
+			return transport.Result{Stdout: `@@journal
+persistent
+@@nightly:service
+LoadState=loaded
+ActiveState=failed
+Result=timeout
+ExecMainStatus=143
+@@nightly:timer
+LoadState=loaded
+ActiveState=active
+@@nightly:run
+@@nightly:history
+`}, true
+		}
+		return transport.Result{}, false
+	}}
+	e := New(cfg, testProject(t), f, Options{Out: &bytes.Buffer{}, Sleep: noSleep})
+	statuses, err := e.scheduleStatuses(context.Background())
+	if err != nil {
+		t.Fatal(err)
+	}
+	got := statuses[0]
+	if !got.Diverged {
+		t.Fatalf("a failing job on a pre-record host reads as clean: %#v", got)
+	}
+	issues := strings.Join(got.Issues, "; ")
+	if !strings.Contains(issues, "last run failed: timeout (exit 143)") || !strings.Contains(issues, "ob schedule apply") {
+		t.Fatalf("issue does not name the failure or the remedy: %#v", got.Issues)
+	}
+}
+
+// Once records exist they are the verdict, and systemd's retained result must
+// not raise a second, contradictory issue.
+func TestScheduleStatusPrefersRecordsOverSystemdResult(t *testing.T) {
+	cfg := testConfig()
+	cfg.Workloads["nightly"] = app.Workload{
+		Role: app.RoleJob, When: "manual", DataEffect: "none",
+		Schedule: &app.JobSchedule{Cron: "0 2 * * *", Timezone: "UTC", Timeout: "1h", CatchUp: true},
+	}
+	f := &transport.Fake{Dynamic: func(cmd string) (transport.Result, bool) {
+		if strings.Contains(cmd, "systemctl show") {
+			return transport.Result{Stdout: `@@journal
+persistent
+@@nightly:service
+LoadState=loaded
+ActiveState=inactive
+Result=timeout
+ExecMainStatus=143
+@@nightly:timer
+LoadState=loaded
+ActiveState=active
+@@nightly:run
+@@nightly:history
+{"run":"a1b2c3d4e5f60718293a4b5c6d7e8f90","job":"nightly","trigger":"timer","started_at":"2026-09-05T02:00:01Z","finished_at":"2026-09-05T02:01:02Z","duration_s":61,"attempts":1,"exit_status":0,"outcome":"success","inputs":{}}
+`}, true
+		}
+		return transport.Result{}, false
+	}}
+	e := New(cfg, testProject(t), f, Options{Out: &bytes.Buffer{}, Sleep: noSleep})
+	statuses, err := e.scheduleStatuses(context.Background())
+	if err != nil {
+		t.Fatal(err)
+	}
+	if got := statuses[0]; got.Diverged || got.LastOutcome != "success" {
+		t.Fatalf("a stale systemd result outvoted the record: %#v", got)
+	}
+}
diff --git a/site/src/content/docs/guides/schedule-a-job.mdx b/site/src/content/docs/guides/schedule-a-job.mdx
index 79087c4..23b7814 100644
--- a/site/src/content/docs/guides/schedule-a-job.mdx
+++ b/site/src/content/docs/guides/schedule-a-job.mdx
@@ -132,6 +132,11 @@ under the same application lock, schedule mutex, fence, and journal boundary as
 a deploy, but it does not stage or activate a release. Run it after upgrading
 Onebox when an application may not be deployed again soon.
 
+Run records are written by the unit, so a host whose units predate them has
+none until this command or a deploy rewrites them. Until then `ob status` falls
+back to what systemd retained, reports a failure as it always did, and says
+that no run record exists yet.
+
 ## Every run leaves a record
 
 When a run ends, for any reason, the unit's `ExecStopPost` writes one record