diff --git a/apps/desktop/src/lib/useConversationMessages.ts b/apps/desktop/src/lib/useConversationMessages.ts
index 3b10179..1e4c9ab 100644
--- a/apps/desktop/src/lib/useConversationMessages.ts
+++ b/apps/desktop/src/lib/useConversationMessages.ts
@@ -1,3 +1,4 @@
+import { fetchPeerPublicKeys } from '@chat-app/shared/auth';
 import {
   type AttachmentHandle,
   type DecryptedMessage,
@@ -8,6 +9,8 @@ import {
   MAX_ATTACHMENT_BYTES,
   type MessageWithCipher,
   sendEncryptedMessage,
+  shareConvKeyToUser,
+  tryGetConvKey,
 } from '@chat-app/shared/chat';
 import { bytesToPgHex, pgBytesToBytes } from '@chat-app/shared/supabase';
 import { useCallback, useEffect, useMemo, useRef, useState } from 'react';
@@ -98,6 +101,96 @@ export function useConversationMessages({ conversationId, userId, deviceId }: Ar
     });
   }, [userId]);
 
+  // Proactive rewrap sweep: when a conversation opens, walk every accepted
+  // member and ensure the active conv-key has a `recipient_user_id` bundle
+  // for them. Members who are missing one (typically peers who haven't yet
+  // migrated to the per-user key model) get a best-effort wrap from the
+  // local conv-key handle. Closes the legacy migration gap so peer B can
+  // read on first unlock without manual intervention from A.
+  useEffect(() => {
+    if (!conversationId || !userId) return;
+    let cancelled = false;
+    const run = async (): Promise<void> => {
+      // Wait for the private key ref to be populated. Loop with backoff
+      // because it's set asynchronously by another effect; bail if the
+      // conversation switches.
+      for (let i = 0; i < 20 && !privateKeyRef.current && !cancelled; i++) {
+        await new Promise((r) => setTimeout(r, 100));
+      }
+      const priv = privateKeyRef.current;
+      if (!priv || cancelled) return;
+
+      try {
+        const { data: convRow, error: convErr } = await supabase
+          .from('conversations')
+          .select('active_key_version')
+          .eq('id', conversationId)
+          .single();
+        if (convErr || !convRow) return;
+        // db-types snapshot predates the active_key_version column; cast via unknown.
+        const version = (convRow as unknown as { active_key_version: number }).active_key_version;
+
+        const handle = await tryGetConvKey(supabase, conversationId, userId, priv, version);
+        if (!handle || cancelled) return;
+
+        const { data: members, error: mErr } = await supabase
+          .from('conversation_members')
+          .select('user_id, accepted')
+          .eq('conversation_id', conversationId);
+        if (mErr || !members) return;
+        const memberIds = (members as Array<{ user_id: string; accepted: boolean }>)
+          .filter((m) => m.accepted && m.user_id !== userId)
+          .map((m) => m.user_id);
+        if (memberIds.length === 0) return;
+
+        const peers = await fetchPeerPublicKeys(supabase, memberIds);
+        for (const peer of peers) {
+          if (cancelled) return;
+          const { count, error: cntErr } = await (
+            supabase as unknown as {
+              from: (t: string) => {
+                select: (s: string, o?: object) => {
+                  eq: (...a: unknown[]) => {
+                    eq: (...a: unknown[]) => {
+                      eq: (
+                        ...a: unknown[]
+                      ) => Promise<{ count: number | null; error: unknown }>;
+                    };
+                  };
+                };
+              };
+            }
+          )
+            .from('conversation_keys')
+            .select('recipient_user_id', { count: 'exact', head: true })
+            .eq('conversation_id', conversationId)
+            .eq('recipient_user_id', peer.userId)
+            .eq('key_version', version);
+          if (cntErr) continue;
+          if ((count ?? 0) === 0) {
+            try {
+              await shareConvKeyToUser(
+                supabase,
+                conversationId,
+                peer.userId,
+                peer.publicKey,
+                { userId, privateKey: priv },
+              );
+            } catch (err) {
+              console.warn('proactive rewrap failed for', peer.userId, err);
+            }
+          }
+        }
+      } catch (err) {
+        console.warn('proactive rewrap sweep failed', err);
+      }
+    };
+    void run();
+    return () => {
+      cancelled = true;
+    };
+  }, [conversationId, userId]);
+
   const decryptBatch = useCallback(
     async (messages: MessageWithCipher[]): Promise<DecryptedMessage[]> => {
       const priv = privateKeyRef.current;