diff --git a/packages/adapters/src/messaging-delivery.test.ts b/packages/adapters/src/messaging-delivery.test.ts
index 2d06a41..ec15a39 100644
--- a/packages/adapters/src/messaging-delivery.test.ts
+++ b/packages/adapters/src/messaging-delivery.test.ts
@@ -151,14 +151,24 @@ function createDeps(overrides: {
           where,
           data,
         }: {
-          where: { id?: string; providerHandle?: string; status?: string };
+          where: {
+            id?: string;
+            providerHandle?: string;
+            status?: string | { in: string[] };
+          };
           data: Record<string, unknown>;
         }) => {
           let count = 0;
           for (const row of rows) {
             if (where.id && row.id !== where.id) continue;
             if (where.providerHandle && row.providerHandle !== where.providerHandle) continue;
-            if (where.status && row.status !== where.status) continue;
+            if (where.status) {
+              const allowed =
+                typeof where.status === "string"
+                  ? [where.status]
+                  : where.status.in;
+              if (!allowed.includes(String(row.status))) continue;
+            }
             Object.assign(row, data);
             count += 1;
           }
@@ -540,7 +550,7 @@ describe("deliverMessagingOutbound", () => {
 });
 
 describe("applyMessagingOutboundStatus", () => {
-  it("maps terminal statuses onto outbox rows by handle", async () => {
+  it("maps terminal statuses onto pending outbox rows by handle", async () => {
     const deps = createDeps({});
     await applyMessagingOutboundStatus(deps.prisma, {
       type: "status",
@@ -549,7 +559,7 @@ describe("applyMessagingOutboundStatus", () => {
       status: "ERROR",
     });
     expect(deps.prisma.messagingOutbound.updateMany).toHaveBeenCalledWith({
-      where: { providerHandle: "h-1" },
+      where: { providerHandle: "h-1", status: { in: ["pending"] } },
       data: { status: "failed" },
     });
 
@@ -560,7 +570,7 @@ describe("applyMessagingOutboundStatus", () => {
       status: "DELIVERED",
     });
     expect(deps.prisma.messagingOutbound.updateMany).toHaveBeenCalledWith({
-      where: { providerHandle: "h-2" },
+      where: { providerHandle: "h-2", status: { in: ["pending", "sent"] } },
       data: { status: "sent" },
     });
 
@@ -572,6 +582,62 @@ describe("applyMessagingOutboundStatus", () => {
     });
     expect(deps.prisma.messagingOutbound.updateMany).toHaveBeenCalledTimes(2);
   });
+
+  it("does not regress a sent row when a late ERROR webhook arrives", async () => {
+    const deps = createDeps({
+      outboundRows: [
+        {
+          id: "out-delivered",
+          idempotencyKey: "dm:1",
+          kind: "dm",
+          identityId: "mi-1",
+          body: "already delivered",
+          status: "sent",
+          providerHandle: "h-late-error",
+        },
+      ],
+    });
+    await applyMessagingOutboundStatus(deps.prisma, {
+      type: "status",
+      provider: "sendblue",
+      handle: "h-late-error",
+      status: "ERROR",
+    });
+
+    expect(deps.rows[0]).toEqual(expect.objectContaining({ status: "sent" }));
+    expect(deps.prisma.messagingOutbound.updateMany).toHaveBeenCalledWith({
+      where: { providerHandle: "h-late-error", status: { in: ["pending"] } },
+      data: { status: "failed" },
+    });
+  });
+
+  it("does not upgrade a failed row when a late DELIVERED webhook arrives", async () => {
+    const deps = createDeps({
+      outboundRows: [
+        {
+          id: "out-failed",
+          idempotencyKey: "dm:2",
+          kind: "dm",
+          identityId: "mi-1",
+          body: "gave up",
+          status: "failed",
+          providerHandle: "h-late-sent",
+        },
+      ],
+    });
+    await applyMessagingOutboundStatus(deps.prisma, {
+      type: "status",
+      provider: "sendblue",
+      handle: "h-late-sent",
+      status: "DELIVERED",
+    });
+
+    expect(deps.rows[0]).toEqual(expect.objectContaining({ status: "failed" }));
+    expect(deps.prisma.messagingOutbound.updateMany).toHaveBeenCalledWith({
+      where: { providerHandle: "h-late-sent", status: { in: ["pending", "sent"] } },
+      data: { status: "sent" },
+    });
+  });
 });
 
 function createChannelDeps(
diff --git a/packages/adapters/src/messaging-delivery.ts b/packages/adapters/src/messaging-delivery.ts
index 3429d5e..2ed3a48 100644
--- a/packages/adapters/src/messaging-delivery.ts
+++ b/packages/adapters/src/messaging-delivery.ts
@@ -468,20 +468,32 @@ function messagingOutboundRetryDelayMs(attempts: number): number {
   return Math.min(2 ** attempts * 1000, 60_000);
 }
 
+function outboundStatusFromWebhook(event: MessagingOutboundStatus): "failed" | "sent" | null {
+  if (event.status === "ERROR" || event.status === "DECLINED") return "failed";
+  if (event.status === "SENT" || event.status === "DELIVERED") return "sent";
+  return null;
+}
+
+/** Stored statuses that may transition to the webhook target. */
+function allowedSourcesForWebhookTarget(target: "failed" | "sent"): Array<"pending" | "sent" | "failed"> {
+  // Drain claims rows `sent` before the provider acks; a late ERROR must not
+  // regress a delivered row. Terminal `failed` must not be upgraded by SENT.
+  if (target === "failed") return ["pending"];
+  return ["pending", "sent"];
+}
+
 /** Outbound status webhooks update outbox rows by provider handle. */
 export async function applyMessagingOutboundStatus(
   prisma: PrismaClient,
   event: MessagingOutboundStatus,
 ): Promise<void> {
-  const status =
-    event.status === "ERROR" || event.status === "DECLINED"
-      ? "failed"
-      : event.status === "SENT" || event.status === "DELIVERED"
-        ? "sent"
-        : null;
+  const status = outboundStatusFromWebhook(event);
   if (!status) return;
   await prisma.messagingOutbound.updateMany({
-    where: { providerHandle: event.handle },
+    where: {
+      providerHandle: event.handle,
+      status: { in: allowedSourcesForWebhookTarget(status) },
+    },
     data: { status },
   });
 }