diff --git a/src/app/api/chat/keys/route.ts b/src/app/api/chat/keys/route.ts
index fcab630..87c6c69 100644
--- a/src/app/api/chat/keys/route.ts
+++ b/src/app/api/chat/keys/route.ts
@@ -21,6 +21,7 @@ export async function GET(request: NextRequest) {
 
     const bundle = await db.query.chatDeviceBundles.findFirst({
       where: eq(chatDeviceBundles.did, did),
+      orderBy: (bundles, { desc }) => [desc(bundles.lastSeenAt)],
     });
 
     console.log('[Chat Keys GET] Found local bundle:', bundle ? 'YES' : 'NO');
diff --git a/src/app/chat/page.tsx b/src/app/chat/page.tsx
index 6640e0d..4b61de4 100644
--- a/src/app/chat/page.tsx
+++ b/src/app/chat/page.tsx
@@ -150,7 +150,7 @@ export default function ChatPage() {
                                 if (msg.isSentByMe && envelope.recipientDid) {
                                     // I'm the sender, so I need the recipient's public key to decrypt my own message
                                     try {
-                                        const keyRes = await fetch(`/api/chat/keys?did=${encodeURIComponent(envelope.recipientDid)}`);
+                                        const keyRes = await fetch(`/api/chat/keys?did=${encodeURIComponent(envelope.recipientDid)}`, { cache: 'no-store' });
                                         if (keyRes.ok) {
                                             const keyData = await keyRes.json();
                                             otherPartyPublicKey = keyData.publicKey;
diff --git a/src/lib/hooks/useSodiumChat.ts b/src/lib/hooks/useSodiumChat.ts
index ae5bcec..63cf649 100644
--- a/src/lib/hooks/useSodiumChat.ts
+++ b/src/lib/hooks/useSodiumChat.ts
@@ -64,7 +64,7 @@ export function useSodiumChat() {
           if (!user.did) {
             throw new Error('User DID not available');
           }
-          const checkResponse = await fetch(`/api/chat/keys?did=${encodeURIComponent(user.did)}`);
+          const checkResponse = await fetch(`/api/chat/keys?did=${encodeURIComponent(user.did)}`, { cache: 'no-store' });
 
           let shouldPublish = false;