diff --git a/app/routes/app.invoices.tsx b/app/routes/app.invoices.tsx
index 5901367..23a322a 100644
--- a/app/routes/app.invoices.tsx
+++ b/app/routes/app.invoices.tsx
@@ -234,13 +234,16 @@ function FilterChip({
 
 function OrderRow({ order }: { order: RecentOrder }) {
   const fetcher = useFetcher<{ ok: boolean; error?: string; invoiceNumber?: string }>();
+  const sendFetcher = useFetcher<{ ok: boolean; error?: string }>();
   const isBusy = fetcher.state !== "idle";
+  const isSending = sendFetcher.state !== "idle";
   const isCancelReissue = order.hasInvoice && order.invoiceSent;
   const buttonLabel = !order.hasInvoice
     ? "Generate"
     : order.invoiceSent
       ? "Cancel & reissue"
       : "Regenerate";
+  const sendLabel = order.invoiceSent ? "Re-send" : "Send";
 
   return (
     <s-table-row>
@@ -271,6 +274,9 @@ function OrderRow({ order }: { order: RecentOrder }) {
             {fetcher.data?.error ? (
               <s-text tone="critical">{fetcher.data.error}</s-text>
             ) : null}
+            {sendFetcher.data?.error ? (
+              <s-text tone="critical">{sendFetcher.data.error}</s-text>
+            ) : null}
           </s-stack>
         ) : (
           <s-text tone="neutral">—</s-text>
@@ -289,13 +295,23 @@ function OrderRow({ order }: { order: RecentOrder }) {
             ) : null}
             <s-button
               type="submit"
-              disabled={isBusy}
+              disabled={isBusy || isSending}
               variant={order.hasInvoice ? "secondary" : "primary"}
               tone={isCancelReissue ? "critical" : "auto"}
             >
               {isBusy ? "Working…" : buttonLabel}
             </s-button>
           </fetcher.Form>
+          <sendFetcher.Form method="post" action={`/api/orders/${order.numericId}/invoice`}>
+            <input type="hidden" name="action" value="send" />
+            <s-button
+              type="submit"
+              disabled={isBusy || isSending}
+              variant={order.hasInvoice && !order.invoiceSent ? "primary" : "secondary"}
+            >
+              {isSending ? "Sending…" : sendLabel}
+            </s-button>
+          </sendFetcher.Form>
         </s-stack>
       </s-table-cell>
     </s-table-row>
diff --git a/extensions/invoice-order-block/src/BlockExtension.tsx b/extensions/invoice-order-block/src/BlockExtension.tsx
index 8aac57b..e7a0910 100644
--- a/extensions/invoice-order-block/src/BlockExtension.tsx
+++ b/extensions/invoice-order-block/src/BlockExtension.tsx
@@ -30,11 +30,16 @@ function Extension() {
   const [payload, setPayload] = useState<Payload | null>(null);
   const [loading, setLoading] = useState(true);
   const [error, setError] = useState<string | null>(null);
+  const [busy, setBusy] = useState<null | "generate" | "send" | "cancel_reissue">(null);
+  const [actionError, setActionError] = useState<string | null>(null);
+  const [actionInfo, setActionInfo] = useState<string | null>(null);
+  const [reloadKey, setReloadKey] = useState(0);
 
   useEffect(() => {
     if (!orderId) return;
     let cancelled = false;
     (async () => {
+      setLoading(true);
       try {
         const res = await fetch(`/api/orders/${orderId}/invoice`);
         if (!res.ok) throw new Error(`HTTP ${res.status}`);
@@ -49,7 +54,36 @@ function Extension() {
     return () => {
       cancelled = true;
     };
-  }, [orderId]);
+  }, [orderId, reloadKey]);
+
+  async function trigger(action: "generate" | "send" | "cancel_reissue") {
+    if (!orderId) return;
+    setBusy(action);
+    setActionError(null);
+    setActionInfo(null);
+    try {
+      const body = new URLSearchParams({ action });
+      const res = await fetch(`/api/orders/${orderId}/invoice`, { method: "POST", body });
+      const txt = await res.text();
+      if (!res.ok) throw new Error(`HTTP ${res.status}: ${txt.slice(0, 200)}`);
+      setActionInfo(
+        action === "send"
+          ? "Invoice email sent."
+          : action === "cancel_reissue"
+            ? "Cancelled and reissued."
+            : "Invoice generated.",
+      );
+      setReloadKey((k) => k + 1);
+    } catch (e: any) {
+      setActionError(e?.message ?? "Action failed");
+    } finally {
+      setBusy(null);
+    }
+  }
+
+  const latest = payload?.latest;
+  const hasInvoice = !!latest && !latest.cancelledAt;
+  const sent = !!latest?.sentAt;
 
   return (
     <s-admin-block heading="Invoice">
@@ -57,21 +91,53 @@ function Extension() {
         <s-text>Loading…</s-text>
       ) : error ? (
         <s-banner tone="critical">{error}</s-banner>
-      ) : !payload?.latest ? (
-        <s-text>No invoice yet for this order.</s-text>
       ) : (
         <s-stack gap="200">
-          <s-text weight="bold">{payload.latest.invoiceNumber} (v{payload.latest.version})</s-text>
-          <s-text>Issued {new Date(payload.latest.issuedAt).toLocaleDateString()}</s-text>
-          <s-badge tone={payload.latest.sentAt ? "success" : "info"}>
-            {payload.latest.sentAt ? "Sent" : "Not sent"}
-          </s-badge>
-          {payload.latest.pdfUrl ? (
-            <s-link href={payload.latest.pdfUrl} target="_blank">View PDF</s-link>
-          ) : null}
-          {payload.history.length > 1 ? (
-            <s-text tone="subdued">{payload.history.length} versions in history</s-text>
-          ) : null}
+          {latest ? (
+            <s-stack gap="100">
+              <s-text weight="bold">
+                {latest.invoiceNumber} (v{latest.version})
+              </s-text>
+              <s-text>Issued {new Date(latest.issuedAt).toLocaleDateString()}</s-text>
+              <s-badge tone={sent ? "success" : "info"}>{sent ? "Sent" : "Not sent"}</s-badge>
+              {latest.pdfUrl ? (
+                <s-link href={latest.pdfUrl} target="_blank">
+                  View PDF
+                </s-link>
+              ) : null}
+              {payload!.history.length > 1 ? (
+                <s-text tone="subdued">{payload!.history.length} versions in history</s-text>
+              ) : null}
+            </s-stack>
+          ) : (
+            <s-text>No invoice yet for this order.</s-text>
+          )}
+
+          {actionError ? <s-banner tone="critical">{actionError}</s-banner> : null}
+          {actionInfo ? <s-banner tone="success">{actionInfo}</s-banner> : null}
+
+          <s-stack direction="inline" gap="100">
+            {!hasInvoice ? (
+              <s-button onClick={() => trigger("generate")} disabled={busy !== null}>
+                {busy === "generate" ? "Generating…" : "Generate"}
+              </s-button>
+            ) : !sent ? (
+              <s-button onClick={() => trigger("generate")} disabled={busy !== null}>
+                {busy === "generate" ? "Working…" : "Regenerate"}
+              </s-button>
+            ) : (
+              <s-button
+                onClick={() => trigger("cancel_reissue")}
+                disabled={busy !== null}
+                tone="critical"
+              >
+                {busy === "cancel_reissue" ? "Working…" : "Cancel & reissue"}
+              </s-button>
+            )}
+            <s-button onClick={() => trigger("send")} disabled={busy !== null}>
+              {busy === "send" ? "Sending…" : sent ? "Re-send" : "Send"}
+            </s-button>
+          </s-stack>
         </s-stack>
       )}
     </s-admin-block>