diff --git a/internal/server/http/catchup.go b/internal/server/http/catchup.go
new file mode 100644
index 0000000..15ae429
--- /dev/null
+++ b/internal/server/http/catchup.go
@@ -0,0 +1,29 @@
+// catchup.go — server-side catch-up for intermittent (non-always-on)
+// hosts. When such a host reconnects we wait a short settle window,
+// then dispatch a backup for any schedule whose window elapsed while
+// the host was asleep. This is separate from pending_runs: a host that
+// was asleep never fired its local cron, so no pending row exists.
+package http
+
+import (
+	"time"
+)
+
+// scheduleOverdue reports whether a schedule's most recent expected
+// fire is newer than the host's last successful backup — i.e. a window
+// passed with no backup. A nil lastBackup means "never backed up" and
+// is always overdue (provided the cron parses). An unparseable cron is
+// treated as not-overdue so a bad expression can never trigger a
+// surprise dispatch. Uses the same cronParser the agent's scheduler
+// and schedule validation use, so interpretation is identical.
+func scheduleOverdue(cronExpr string, lastBackup *time.Time, now time.Time) bool {
+	sched, err := cronParser.Parse(cronExpr)
+	if err != nil {
+		return false
+	}
+	if lastBackup == nil {
+		return true
+	}
+	next := sched.Next(*lastBackup)
+	return !next.After(now)
+}
diff --git a/internal/server/http/catchup_test.go b/internal/server/http/catchup_test.go
new file mode 100644
index 0000000..a9de720
--- /dev/null
+++ b/internal/server/http/catchup_test.go
@@ -0,0 +1,41 @@
+package http
+
+import (
+	"testing"
+	"time"
+)
+
+func TestScheduleOverdue(t *testing.T) {
+	mustParse := func(s string) time.Time {
+		t.Helper()
+		v, err := time.Parse(time.RFC3339, s)
+		if err != nil {
+			t.Fatalf("parse %q: %v", s, err)
+		}
+		return v
+	}
+	daily := "0 2 * * *" // 02:00 every day
+
+	cases := []struct {
+		name       string
+		cron       string
+		lastBackup *time.Time
+		now        time.Time
+		want       bool
+	}{
+		{name: "never backed up is overdue", cron: daily, lastBackup: nil, now: mustParse("2026-06-15T09:00:00Z"), want: true},
+		{name: "missed last nights window", cron: daily, lastBackup: ptrTime(mustParse("2026-06-13T02:05:00Z")), now: mustParse("2026-06-15T09:00:00Z"), want: true},
+		{name: "backed up after the most recent window", cron: daily, lastBackup: ptrTime(mustParse("2026-06-15T02:05:00Z")), now: mustParse("2026-06-15T09:00:00Z"), want: false},
+		{name: "unparseable cron is never overdue", cron: "not a cron", lastBackup: nil, now: mustParse("2026-06-15T09:00:00Z"), want: false},
+	}
+	for _, c := range cases {
+		t.Run(c.name, func(t *testing.T) {
+			got := scheduleOverdue(c.cron, c.lastBackup, c.now)
+			if got != c.want {
+				t.Fatalf("scheduleOverdue(%q, %v, %v) = %v, want %v", c.cron, c.lastBackup, c.now, got, c.want)
+			}
+		})
+	}
+}
+
+func ptrTime(t time.Time) *time.Time { return &t }