diff --git a/go/e2e/legcomms_redeliver_test.go b/go/e2e/legcomms_redeliver_test.go
new file mode 100644
index 00000000..f961a8ab
--- /dev/null
+++ b/go/e2e/legcomms_redeliver_test.go
@@ -0,0 +1,148 @@
+//go:build podman
+
+package e2e
+
+import (
+	"context"
+	"testing"
+
+	"github.com/RigelBuild/compass/go/internal/store"
+)
+
+// TestCommsOfflineRedeliveryOnSessionStart proves the session-start sweep
+// redelivers a message that accrued while the agent was offline (RIG-3532 T5).
+// "Offline" is a DESPAWN, not a never-started agent: a post to a
+// provisioned-but-idle agent wakes and fresh-starts it (the placement recorded
+// at Provision makes the wake an auto-start), so the message would never be
+// owed. Posting AFTER RemoveWorkspace deletes the placement makes the wake a
+// benign no-placement no-op, so the message stays owed for the next start.
+func TestCommsOfflineRedeliveryOnSessionStart(t *testing.T) {
+	if !podmanUsable() {
+		t.Skip("rootless podman cannot run compass-agent:latest here; skipping the real-stack e2e")
+	}
+
+	ctx := context.Background() // test root, threaded into NewFixture + every primitive
+
+	// Slot 0 settles lifetime 1's warm turn, driven only so the resume has a
+	// persisted transcript to reconstruct; slot 1 settles the resumed turn the
+	// sweep's redelivery of the offline message drives.
+	const warmReply = "canned lifetime-1 warm turn settled OK"
+	const redeliverReply = "canned redelivered turn settled OK"
+	f := NewFixture(ctx, t, WithCannedScript(
+		CannedText(warmReply),
+		CannedText(redeliverReply),
+	))
+
+	accountID, err := f.CreateAgent(ctx, "comms-redeliver", "Comms Offline Redelivery")
+	if err != nil {
+		t.Fatalf("CreateAgent: %v", err)
+	}
+
+	// ── Lifetime 1: provision, drive one turn so the session is resumable ──
+
+	container1, err := f.Provision(ctx, accountID, "comms-redeliver-provision-1")
+	if err != nil {
+		t.Fatalf("Provision (container1): %v", err)
+	}
+	// Reap net: the reparented rootless conmon outlives stack Down, so an explicit
+	// RemoveWorkspace is the reliable reap. Registered before StartSession so a
+	// later failure still tears it down; the mid-test despawn below no-ops this
+	// one idempotently. Best-effort teardown, so the error is deliberately dropped.
+	t.Cleanup(func() {
+		_ = f.RemoveWorkspace(ctx, container1, "comms-redeliver-teardown-1")
+	})
+
+	sessionID, err := f.StartSession(ctx, container1)
+	if err != nil {
+		t.Fatalf("StartSession (container1): %v", err)
+	}
+
+	st, err := store.Open(ctx, f.DSN())
+	if err != nil {
+		t.Fatalf("store.Open: %v", err)
+	}
+	defer st.Close()
+
+	acc, err := adminAgentByHandle(ctx, st, "comms-redeliver")
+	if err != nil {
+		t.Fatalf("AgentByHandle: %v", err)
+	}
+	home := acc.Agent.HomeChannelID
+
+	tail1, err := f.OpenSessionTail(ctx, sessionID)
+	if err != nil {
+		t.Fatalf("OpenSessionTail (lifetime 1): %v", err)
+	}
+	defer tail1.Close()
+
+	warmID, err := f.PostMessage(ctx, string(home), "general", "warm the session so it persists a transcript")
+	if err != nil {
+		t.Fatalf("PostMessage (warm): %v", err)
+	}
+	if err := f.AwaitTurnSettled(ctx, tail1); err != nil {
+		t.Fatalf("AwaitTurnSettled (lifetime 1): %v", err)
+	}
+
+	// Ack the warm message BEFORE teardown so the resume sweep does not redeliver
+	// it too — only the offline post below must be owed at resume time.
+	if err := f.waitDeliveryCursorPast(ctx, st, acc.ID, home, store.MessageID(warmID)); err != nil {
+		t.Fatalf("waitDeliveryCursorPast (warm): %v", err)
+	}
+	// The resume reconstructs the session body from the durable transcript, so the
+	// warm turn must be committed before container1 is torn down.
+	if _, err := f.awaitTranscriptPersisted(ctx, st, sessionID, warmReply); err != nil {
+		t.Fatalf("awaitTranscriptPersisted (warm reply): %v", err)
+	}
+
+	// Despawn boundary: RemoveWorkspace deletes the placement, which is what makes
+	// the offline post's wake a no-placement no-op instead of an auto-start.
+	if err := f.RemoveWorkspace(ctx, container1, "comms-redeliver-teardown-1"); err != nil {
+		t.Fatalf("RemoveWorkspace (despawn boundary): %v", err)
+	}
+
+	offlineID, err := f.PostMessage(ctx, string(home), "general", "message accrued while the agent is offline")
+	if err != nil {
+		t.Fatalf("PostMessage (offline): %v", err)
+	}
+
+	// Pre-condition: the offline message IS owed. Without it the post-condition
+	// ("no longer owed") would pass vacuously against a never-owed message.
+	owed, err := st.UndeliveredMessages(ctx, acc.ID)
+	if err != nil {
+		t.Fatalf("UndeliveredMessages (pre-condition): %v", err)
+	}
+	preOwed := false
+	for _, m := range owed[home] {
+		if m.ID == store.MessageID(offlineID) {
+			preOwed = true
+			break
+		}
+	}
+	if !preOwed {
+		t.Fatalf("offline message %s is not owed before session start; the pre-condition the redelivery proof rests on does not hold", offlineID)
+	}
+
+	// ── Lifetime 2: provision a fresh container, RESUME the logical session ──
+
+	container2, err := f.Provision(ctx, accountID, "comms-redeliver-provision-2")
+	if err != nil {
+		t.Fatalf("Provision (container2): %v", err)
+	}
+	// Reap net for container2, same reparented-conmon reason; registered before
+	// Resume so a Resume failure still tears it down. Best-effort, error dropped.
+	t.Cleanup(func() {
+		_ = f.RemoveWorkspace(ctx, container2, "comms-redeliver-teardown-2")
+	})
+
+	if _, err := f.Resume(ctx, container2, sessionID); err != nil {
+		t.Fatalf("Resume (container2): %v", err)
+	}
+
+	// Post-condition read DURABLY from the store, not a live tail: the start-sweep
+	// is enqueued INSIDE Resume and drained async, so a tail opened after Resume
+	// can miss the redelivery (the RIG-3044 flake shape). The cursor advancing past
+	// the offline message proves the sweep redelivered it and the session acked.
+	if err := f.waitDeliveryCursorPast(ctx, st, acc.ID, home, store.MessageID(offlineID)); err != nil {
+		t.Fatalf("waitDeliveryCursorPast (offline redelivery): %v", err)
+	}
+}