diff --git a/src/app/api/webhooks/documenso/route.ts b/src/app/api/webhooks/documenso/route.ts
index c56ff135..c9ccbb59 100644
--- a/src/app/api/webhooks/documenso/route.ts
+++ b/src/app/api/webhooks/documenso/route.ts
@@ -97,6 +97,13 @@ type DocumensoRecipient = {
   token?: string | null;
   signingToken?: string | null;
   signingUrl?: string | null;
+  /** Free-text reason the recipient typed into Documenso's reject dialog.
+   *  v2 payloads carry `rejectionReason`; some 1.x payloads use the
+   *  legacy `declineReason` field name. Either way we surface the
+   *  cleartext to the rep so they don't have to log into Documenso to
+   *  see why a deal stalled. */
+  rejectionReason?: string | null;
+  declineReason?: string | null;
 };
 
 type DocumensoWebhookBody = {
@@ -279,9 +286,18 @@ async function handleDocumensoWebhook(req: NextRequest): Promise<NextResponse> {
           const rejecting = recipients.find(
             (r) => r.signingStatus === 'REJECTED' || r.signingStatus === 'DECLINED',
           );
+          // Documenso uses two field names across versions: v2
+          // `rejectionReason`, some 1.x payloads `declineReason`. Coalesce
+          // so handlers downstream see one stable field. Empty string
+          // (vs null) normalised to null so the UI's "no reason given"
+          // copy fires consistently.
+          const rawReason = rejecting?.rejectionReason ?? rejecting?.declineReason ?? null;
+          const rejectionReason =
+            rawReason && rawReason.trim().length > 0 ? rawReason.trim() : null;
           await handleDocumentRejected({
             documentId: documensoId,
             recipientEmail: rejecting?.email,
+            rejectionReason,
             signatureHash,
             ...portScope,
           });
diff --git a/src/components/documents/signing-progress.tsx b/src/components/documents/signing-progress.tsx
index 13ab5198..a2f078b2 100644
--- a/src/components/documents/signing-progress.tsx
+++ b/src/components/documents/signing-progress.tsx
@@ -397,20 +397,26 @@ export function SigningProgress({ documentId, signers }: SigningProgressProps) {
                   • `invitedAt !== null` → "Send reminder"
                     (Documenso-side nudge, rate-limited per cooldown).
                   • Signed/declined → no action buttons. */}
-              {signer.status === 'pending' && signer.signingUrl ? (
+              {signer.status === 'pending' ? (
                 <Button
-                  variant="ghost"
+                  variant="outline"
                   size="sm"
-                  className="h-7 shrink-0 gap-1.5 px-2.5 text-xs text-muted-foreground hover:text-foreground [&_svg]:size-3"
+                  className="h-7 shrink-0 gap-1.5 px-2.5 text-xs [&_svg]:size-3"
+                  disabled={!signer.signingUrl}
                   onClick={async () => {
+                    if (!signer.signingUrl) return;
                     try {
-                      await navigator.clipboard.writeText(signer.signingUrl!);
+                      await navigator.clipboard.writeText(signer.signingUrl);
                       toast.success(`Signing link for ${signer.signerName} copied`);
                     } catch {
                       toast.error('Could not copy to clipboard');
                     }
                   }}
-                  title="Copy this signer's Documenso URL to the clipboard - for QA or manual delivery."
+                  title={
+                    signer.signingUrl
+                      ? "Copy this signer's signing link to your clipboard so you can share it directly (Slack, WhatsApp, in person) without going through email."
+                      : 'Signing URL is not available yet — Documenso issues it once the document has been sent.'
+                  }
                 >
                   <Link2 />
                   Copy link
diff --git a/src/components/documents/upload-for-signing-dialog.tsx b/src/components/documents/upload-for-signing-dialog.tsx
index 8f20cfe3..904923c0 100644
--- a/src/components/documents/upload-for-signing-dialog.tsx
+++ b/src/components/documents/upload-for-signing-dialog.tsx
@@ -152,6 +152,45 @@ const RECIPIENT_COLORS = [
   'rgb(20 184 166)', // teal-500
 ];
 
+/**
+ * Display label + colour tint for the three Documenso recipient roles.
+ * Surfaced as a small pill next to each recipient in the placement
+ * step's sidebar AND in the FieldSidePanel's assignment dropdown so
+ * the rep sees the role context without hunting for it in step 2.
+ *
+ *   - SIGNER: active responsibility (must sign + fill fields). Blue.
+ *   - APPROVER: gate before signers (approves before the envelope
+ *     reaches the next recipient). Amber to read as oversight, not
+ *     blocker.
+ *   - CC: receives the final document for awareness; no action. Muted.
+ */
+const RECIPIENT_ROLE_META: Record<Recipient['role'], { label: string; className: string }> = {
+  SIGNER: {
+    label: 'Signer',
+    className: 'bg-blue-100 text-blue-900 border-blue-200',
+  },
+  APPROVER: {
+    label: 'Approver',
+    className: 'bg-amber-100 text-amber-900 border-amber-200',
+  },
+  CC: {
+    label: 'CC',
+    className: 'bg-slate-100 text-slate-700 border-slate-200',
+  },
+};
+
+function RecipientRoleBadge({ role }: { role: Recipient['role'] }) {
+  const meta = RECIPIENT_ROLE_META[role];
+  return (
+    <span
+      className={`inline-flex items-center rounded-full border px-1.5 py-0 text-xs font-medium ${meta.className}`}
+      title={`Role: ${meta.label}`}
+    >
+      {meta.label}
+    </span>
+  );
+}
+
 export interface UploadForSigningEntity {
   type: 'client' | 'company' | 'yacht';
   id: string;
@@ -1106,15 +1145,27 @@ function FieldPlacementStep({
         )}
         <hr className="my-3 border-muted-foreground/20" />
         <p className="text-xs font-medium text-muted-foreground mb-2">Recipients</p>
-        <div className="space-y-1">
+        <div className="space-y-2">
           {recipients.map((r, i) => (
-            <div key={i} className="text-xs flex items-center gap-2">
+            <div key={i} className="flex items-start gap-2 text-xs">
               <span
-                className="size-2 rounded-full shrink-0"
+                className="mt-1 size-2 rounded-full shrink-0"
                 style={{ backgroundColor: RECIPIENT_COLORS[i % RECIPIENT_COLORS.length] }}
                 aria-hidden
               />
-              <span className="truncate">{r.name || r.email || `#${r.signingOrder}`}</span>
+              <div className="min-w-0 flex-1">
+                <div className="flex items-center gap-1.5">
+                  <span className="truncate font-medium">{r.name || `#${r.signingOrder}`}</span>
+                  <RecipientRoleBadge role={r.role} />
+                </div>
+                {/* Email shown separately from name so reps with duplicate
+                    names (e.g. multiple "Matt" recipients) can still tell
+                    rows apart. Empty/blank emails fall back to a muted
+                    placeholder so the row doesn't shift size. */}
+                <p className="truncate text-muted-foreground" title={r.email}>
+                  {r.email || 'no email set'}
+                </p>
+              </div>
             </div>
           ))}
         </div>
@@ -1396,7 +1447,7 @@ function FieldSidePanel({
         </Select>
       </div>
       <div className="space-y-1.5">
-        <Label className="text-xs">Recipient</Label>
+        <Label className="text-xs">Assign this field to</Label>
         <Select
           value={String(field.recipientIndex)}
           onValueChange={(v) => onUpdate({ recipientIndex: Number(v) })}
@@ -1407,11 +1458,25 @@ function FieldSidePanel({
           <SelectContent>
             {recipients.map((r, i) => (
               <SelectItem key={i} value={String(i)}>
-                #{r.signingOrder} {r.name || r.email}
+                <span className="flex flex-col items-start gap-0.5 text-left">
+                  <span className="flex items-center gap-1.5">
+                    <span className="font-medium">
+                      #{r.signingOrder} {r.name || `Recipient ${r.signingOrder}`}
+                    </span>
+                    <RecipientRoleBadge role={r.role} />
+                  </span>
+                  {r.email ? (
+                    <span className="text-xs text-muted-foreground">{r.email}</span>
+                  ) : null}
+                </span>
               </SelectItem>
             ))}
           </SelectContent>
         </Select>
+        <p className="text-xs text-muted-foreground">
+          Whoever is selected here is the only person who will see and fill this field when the
+          document is sent for signing.
+        </p>
       </div>
       <div className="grid grid-cols-2 gap-2">
         <div className="space-y-1">
diff --git a/src/jobs/processors/documenso-poll.ts b/src/jobs/processors/documenso-poll.ts
index 18728ea8..73fd1e91 100644
--- a/src/jobs/processors/documenso-poll.ts
+++ b/src/jobs/processors/documenso-poll.ts
@@ -7,6 +7,7 @@ import {
   handleRecipientSigned,
   handleDocumentCompleted,
   handleDocumentExpired,
+  handleDocumentRejected,
 } from '@/lib/services/documents.service';
 import { logger } from '@/lib/logger';
 
@@ -74,6 +75,35 @@ export async function processDocumensoPoll(): Promise<void> {
           'Reconciling expired document from poll',
         );
         await handleDocumentExpired({ documentId: doc.documensoId, portId: doc.portId });
+      } else if (
+        (remoteDoc.status === 'REJECTED' || remoteDoc.status === 'DECLINED') &&
+        doc.status !== 'rejected'
+      ) {
+        // Rejection / decline reconcile — mirrors the webhook handler's
+        // logic so a missed `DOCUMENT_REJECTED` / `DOCUMENT_DECLINED`
+        // webhook delivery (stale tunnel URL, signature mismatch, etc.)
+        // still converges within one poll cycle. Finds the rejecting
+        // recipient by status, plucks the free-text reason if Documenso
+        // carried one, hands off to the same handler the webhook uses
+        // — so document_events, audit log, notification, and UI all
+        // see the same shape regardless of delivery path.
+        const rejecting = remoteDoc.recipients.find(
+          (r) => r.status === 'REJECTED' || r.status === 'DECLINED',
+        );
+        logger.info(
+          {
+            documentId: doc.id,
+            portId: doc.portId,
+            rejectingEmail: rejecting?.email ?? null,
+          },
+          'Reconciling rejected document from poll',
+        );
+        await handleDocumentRejected({
+          documentId: doc.documensoId,
+          recipientEmail: rejecting?.email,
+          rejectionReason: rejecting?.rejectionReason ?? null,
+          portId: doc.portId,
+        });
       }
     } catch (err) {
       logger.error(
diff --git a/src/lib/audit.ts b/src/lib/audit.ts
index c1c6f203..38968f24 100644
--- a/src/lib/audit.ts
+++ b/src/lib/audit.ts
@@ -58,6 +58,11 @@ export type AuditAction =
   // and the FTS GENERATED index missed entirely.
   | 'outcome_set'
   | 'outcome_cleared'
+  // Ownership transfer — yacht/company switches owner. Distinct from
+  // `update` so the EntityActivityFeed renders "transferred ownership"
+  // instead of the generic "updated this record." Old/new owner names
+  // surface via the standard fieldChanged + oldValue + newValue trio.
+  | 'transfer'
   // Phase 3 - EOI override / contact promote / yacht spawn from EOI.
   // The DB column is free-text per migration 0073; these strings just
   // formalise the catalogue so the audit-log filter dropdown can surface
diff --git a/src/lib/services/custom-document-upload.service.ts b/src/lib/services/custom-document-upload.service.ts
index d4213983..a2f26d29 100644
--- a/src/lib/services/custom-document-upload.service.ts
+++ b/src/lib/services/custom-document-upload.service.ts
@@ -414,32 +414,57 @@ export async function uploadDocumentForSigning(
 
   // Build email→recipientId map. v2 envelope create returns empty
   // recipients; distribute fills them in. v1 already has them on create.
+  // Note: Documenso de-dupes by email at the envelope level, so multiple
+  // CRM-side Recipient rows that share an email all map to the same
+  // Documenso recipientId. That's fine for field placement — both rows
+  // simply target the same Documenso recipient.
   const emailToRecipientId = new Map<string, string>();
   for (const dr of sentDoc.recipients) {
     if (dr.email) emailToRecipientId.set(dr.email.toLowerCase(), dr.id);
   }
 
-  // Place fields (skipped silently when empty - but we validated above).
-  const placements: DocumensoFieldPlacement[] = fields.map((f) => {
-    const recipient = recipients[f.recipientIndex]!;
-    const recipientId = emailToRecipientId.get(recipient.email.toLowerCase());
-    if (!recipientId) {
-      throw new ConflictError(
-        `Documenso response missing recipientId for ${recipient.email} - cannot place fields`,
-      );
-    }
-    return {
-      recipientId,
-      type: f.type,
-      pageNumber: f.pageNumber,
-      pageX: f.pageX,
-      pageY: f.pageY,
-      pageWidth: f.pageWidth,
-      pageHeight: f.pageHeight,
-      ...(f.fieldMeta ? { fieldMeta: f.fieldMeta } : {}),
-    };
-  });
+  // Build placements + place fields inside a SINGLE try/catch so any
+  // failure — including the synchronous `fields.map` throw when a
+  // recipient can't be matched — triggers the rollback path. Previously
+  // the map's throw bubbled past the try-block wrapping `placeFields()`,
+  // leaving Documenso with the live envelope + recipients but no fields,
+  // and the CRM document row stuck in 'sent' with no signing UI for the
+  // signers (UAT 2026-05-26 — "doc displays in Documenso but is missing
+  // all fields").
   try {
+    const placements: DocumensoFieldPlacement[] = fields.map((f) => {
+      const recipient = recipients[f.recipientIndex]!;
+      const recipientId = emailToRecipientId.get(recipient.email.toLowerCase());
+      if (!recipientId) {
+        // Surface the diagnostic state alongside the error so the rep
+        // doesn't have to guess which email failed to match. Logs both
+        // the looked-up email and the keys Documenso DID return so a
+        // future audit can see whether the mismatch is dedupe-related
+        // or a true populate failure.
+        logger.error(
+          {
+            documentId: docRow.id,
+            documensoEnvelopeId: documensoDoc.id,
+            lookedUpEmail: recipient.email,
+            availableEmails: Array.from(emailToRecipientId.keys()),
+          },
+          'Documenso recipient lookup miss during field placement',
+        );
+        throw new ConflictError(
+          `Documenso response missing recipientId for ${recipient.email} - cannot place fields`,
+        );
+      }
+      return {
+        recipientId,
+        type: f.type,
+        pageNumber: f.pageNumber,
+        pageX: f.pageX,
+        pageY: f.pageY,
+        pageWidth: f.pageWidth,
+        pageHeight: f.pageHeight,
+        ...(f.fieldMeta ? { fieldMeta: f.fieldMeta } : {}),
+      };
+    });
     await placeFields(documensoDoc.id, placements, portId);
   } catch (err) {
     await db
diff --git a/src/lib/services/documenso-client.ts b/src/lib/services/documenso-client.ts
index 89f7c11e..29e617cb 100644
--- a/src/lib/services/documenso-client.ts
+++ b/src/lib/services/documenso-client.ts
@@ -178,21 +178,30 @@ function normalizeDocument(raw: unknown): DocumensoDocument {
     (r.recipients as Array<Record<string, unknown>> | undefined) ??
     (r.Recipient as Array<Record<string, unknown>> | undefined) ??
     [];
-  const recipients = recipientsRaw.map((rec) => ({
-    id: String(rec.recipientId ?? rec.id ?? ''),
-    name: String(rec.name ?? ''),
-    email: String(rec.email ?? ''),
-    role: String(rec.role ?? ''),
-    signingOrder: Number(rec.signingOrder ?? 0),
-    status: String(rec.signingStatus ?? rec.status ?? 'PENDING'),
-    signingUrl: typeof rec.signingUrl === 'string' ? rec.signingUrl : undefined,
-    embeddedUrl: typeof rec.embeddedUrl === 'string' ? rec.embeddedUrl : undefined,
-    // Per-recipient signing token - required on the v1 Recipient model,
-    // present on every v2 envelope-distribute response. Documenso uses
-    // it as the URL tail (`/sign/<token>`) so it also matches what we
-    // see on subsequent webhook deliveries.
-    token: typeof rec.token === 'string' ? rec.token : undefined,
-  }));
+  const recipients = recipientsRaw.map((rec) => {
+    // Coalesce the two field names Documenso has used for rejection
+    // reason across versions. Empty string → undefined so consumers
+    // can `?? null`-fallback cleanly without re-checking truthiness.
+    const rawReason = (rec.rejectionReason ?? rec.declineReason) as string | undefined;
+    const rejectionReason =
+      typeof rawReason === 'string' && rawReason.trim().length > 0 ? rawReason.trim() : undefined;
+    return {
+      id: String(rec.recipientId ?? rec.id ?? ''),
+      name: String(rec.name ?? ''),
+      email: String(rec.email ?? ''),
+      role: String(rec.role ?? ''),
+      signingOrder: Number(rec.signingOrder ?? 0),
+      status: String(rec.signingStatus ?? rec.status ?? 'PENDING'),
+      signingUrl: typeof rec.signingUrl === 'string' ? rec.signingUrl : undefined,
+      embeddedUrl: typeof rec.embeddedUrl === 'string' ? rec.embeddedUrl : undefined,
+      // Per-recipient signing token - required on the v1 Recipient model,
+      // present on every v2 envelope-distribute response. Documenso uses
+      // it as the URL tail (`/sign/<token>`) so it also matches what we
+      // see on subsequent webhook deliveries.
+      token: typeof rec.token === 'string' ? rec.token : undefined,
+      rejectionReason,
+    };
+  });
   return { id, numericId, status, recipients };
 }
 
@@ -224,6 +233,10 @@ export interface DocumensoDocument {
      *  match recipients without leaning on email (which may be reused
      *  across roles). */
     token?: string;
+    /** Free-text rejection reason. v2 payloads use `rejectionReason`;
+     *  some 1.x payloads use the legacy `declineReason`. Coalesced
+     *  here so downstream poll/webhook consumers see one stable field. */
+    rejectionReason?: string;
   }>;
 }
 
diff --git a/src/lib/services/documents.service.ts b/src/lib/services/documents.service.ts
index ba0738fd..ff7ffd23 100644
--- a/src/lib/services/documents.service.ts
+++ b/src/lib/services/documents.service.ts
@@ -1920,6 +1920,12 @@ export async function handleDocumentOpened(eventData: {
 export async function handleDocumentRejected(eventData: {
   documentId: string;
   recipientEmail?: string;
+  /** Free-text reason the rejecting recipient typed into Documenso's
+   *  reject dialog. Coalesced from v2 `rejectionReason` / legacy
+   *  `declineReason` at the webhook boundary. Stored on the rejection
+   *  event row, the audit log, and surfaced in the rep notification so
+   *  the rep doesn't have to bounce to Documenso to read it. */
+  rejectionReason?: string | null;
   signatureHash?: string;
   portId?: string;
 }) {
@@ -1960,7 +1966,10 @@ export async function handleDocumentRejected(eventData: {
       eventType: 'rejected',
       signerId,
       signatureHash: eventData.signatureHash ?? null,
-      eventData: { recipientEmail: eventData.recipientEmail ?? null },
+      eventData: {
+        recipientEmail: eventData.recipientEmail ?? null,
+        rejectionReason: eventData.rejectionReason ?? null,
+      },
     })
     .onConflictDoNothing();
 
@@ -1984,14 +1993,25 @@ export async function handleDocumentRejected(eventData: {
     const targetUserId = interest?.assignedTo ?? null;
     if (targetUserId) {
       const { createNotification } = await import('@/lib/services/notifications.service');
+      // Surface the rejection reason inline when Documenso sent one.
+      // Truncate aggressively (notification bell tiles cap at ~80 chars
+      // before wrapping); full reason still lives on the audit row.
+      const reasonSnippet = eventData.rejectionReason
+        ? eventData.rejectionReason.length > 120
+          ? `${eventData.rejectionReason.slice(0, 117)}…`
+          : eventData.rejectionReason
+        : null;
+      const baseDescription = eventData.recipientEmail
+        ? `${eventData.recipientEmail} declined to sign`
+        : 'A signer declined the EOI';
       void createNotification({
         portId: doc.portId,
         userId: targetUserId,
         type: 'document_rejected',
         title: 'EOI declined',
-        description: eventData.recipientEmail
-          ? `${eventData.recipientEmail} declined to sign - review and regenerate.`
-          : 'A signer declined the EOI - review and regenerate.',
+        description: reasonSnippet
+          ? `${baseDescription}: "${reasonSnippet}" — review and regenerate.`
+          : `${baseDescription} — review and regenerate.`,
         link: `/interests/${doc.interestId}?tab=eoi`,
         entityType: 'document',
         entityId: doc.id,
@@ -2014,6 +2034,7 @@ export async function handleDocumentRejected(eventData: {
     metadata: {
       type: 'document_declined',
       signerEmail: eventData.recipientEmail ?? null,
+      rejectionReason: eventData.rejectionReason ?? null,
     },
     ipAddress: '',
     userAgent: '',