diff --git a/src/app/api/v1/interests/[id]/supplemental-info-request/route.ts b/src/app/api/v1/interests/[id]/supplemental-info-request/route.ts
index 3825fa00..f5959670 100644
--- a/src/app/api/v1/interests/[id]/supplemental-info-request/route.ts
+++ b/src/app/api/v1/interests/[id]/supplemental-info-request/route.ts
@@ -14,9 +14,22 @@ import { getPortEmailConfig } from '@/lib/services/port-config';
  * Generates a one-shot token + emails the client the public form URL.
  */
 export const POST = withAuth(
-  withPermission('interests', 'edit', async (_req: NextRequest, ctx, params) => {
+  withPermission('interests', 'edit', async (req: NextRequest, ctx, params) => {
     try {
       const interestId = params.id as string;
+      // Two-step UX: rep can generate a link without firing the email
+      // (so they can copy + share manually through WhatsApp etc.), then
+      // come back and send the templated email separately. Default stays
+      // `true` for back-compat. The body is optional — older callers
+      // POST with no body and still trigger the email.
+      let shouldSendEmail = true;
+      try {
+        const body = (await req.clone().json()) as { sendEmail?: boolean };
+        if (typeof body?.sendEmail === 'boolean') shouldSendEmail = body.sendEmail;
+      } catch {
+        // No JSON body — keep the default.
+      }
+
       const result = await issueToken({
         interestId,
         portId: ctx.portId,
@@ -32,7 +45,7 @@ export const POST = withAuth(
         ? `${emailCfg.supplementalFormUrl}?token=${encodeURIComponent(result.token)}`
         : `${env.NEXT_PUBLIC_APP_URL}/public/supplemental-info/${result.token}`;
 
-      if (result.clientEmail) {
+      if (shouldSendEmail && result.clientEmail) {
         const html = `
           <p>Hello ${escapeHtml(result.clientName)},</p>
           <p>Before we draft your Expression of Interest, we need to confirm a few details.
@@ -45,7 +58,7 @@ export const POST = withAuth(
             </a>
           </p>
           <p style="color:#64748b;font-size:12px">
-            This link expires on ${result.expiresAt.toUTCString()} and can only be used once.
+            This link expires on ${result.expiresAt.toUTCString()}.
             If you didn't expect this email, please let us know.
           </p>
         `;
@@ -63,7 +76,7 @@ export const POST = withAuth(
         data: {
           link,
           expiresAt: result.expiresAt.toISOString(),
-          emailSent: !!result.clientEmail,
+          emailSent: shouldSendEmail && !!result.clientEmail,
         },
       });
     } catch (error) {
diff --git a/src/components/interests/supplemental-info-request-button.tsx b/src/components/interests/supplemental-info-request-button.tsx
index d6a0aeee..2eb98d50 100644
--- a/src/components/interests/supplemental-info-request-button.tsx
+++ b/src/components/interests/supplemental-info-request-button.tsx
@@ -40,16 +40,19 @@ export function SupplementalInfoRequestButton({ interestId, eoiStatus }: Props)
   const [link, setLink] = useState<string | null>(null);
 
   const mutation = useMutation({
-    mutationFn: () =>
+    mutationFn: (vars: { sendEmail: boolean }) =>
       apiFetch<IssueResponse>(`/api/v1/interests/${interestId}/supplemental-info-request`, {
         method: 'POST',
+        body: vars,
       }),
     onSuccess: (res) => {
       setLink(res.data.link);
       if (res.data.emailSent) {
-        toast.success('Email sent — link also shown below for sharing manually.');
+        toast.success('Email sent. Link also shown below for sharing manually.');
       } else {
-        toast.message('Link generated — no client email on file, share manually.');
+        toast.message(
+          'Link generated. Click "Send by email" to mail it, or copy it to share manually.',
+        );
       }
     },
     onError: (err) =>
@@ -76,11 +79,20 @@ export function SupplementalInfoRequestButton({ interestId, eoiStatus }: Props)
           <Button
             type="button"
             size="sm"
-            onClick={() => mutation.mutate()}
+            variant={link ? 'outline' : 'default'}
+            onClick={() => mutation.mutate({ sendEmail: false })}
+            disabled={mutation.isPending}
+          >
+            {mutation.isPending ? 'Generating…' : link ? 'Regenerate link' : 'Generate link'}
+          </Button>
+          <Button
+            type="button"
+            size="sm"
+            onClick={() => mutation.mutate({ sendEmail: true })}
             disabled={mutation.isPending}
           >
             <Mail className="mr-1.5 size-3.5" aria-hidden />
-            {mutation.isPending ? 'Generating…' : link ? 'Resend' : 'Request more info'}
+            {link ? 'Send by email' : 'Generate + email'}
           </Button>
           {link ? (
             <>