diff --git a/apps/web/src/services/chat.ts b/apps/web/src/services/chat.ts
index 469cbd6..3187b1d 100644
--- a/apps/web/src/services/chat.ts
+++ b/apps/web/src/services/chat.ts
@@ -1,8 +1,8 @@
 import type { Event as NostrEvent } from "nostr-tools";
 import { nip19 } from "nostr-tools";
 import { SimplePool } from "nostr-tools/pool";
-import { fetchChat, postChatMessage, postChatReaction } from "./api";
-import { hasActiveSigner } from "./signer";
+import { fetchChat, fetchChatPubkeys, postChatMessage, postChatReaction } from "./api";
+import { getActiveSigner, hasActiveSigner } from "./signer";
 
 const RELAYS = ["wss://relay.primal.net"];
 const POLL_MS = 2500;
@@ -32,6 +32,7 @@ export type ChatProfile = {
 };
 
 let reactionCache: ChatReaction[] = [];
+let cachedRecipients: string[] | null = null;
 
 export function canSendChat(): boolean {
   return hasActiveSigner();
@@ -49,13 +50,13 @@ export function pubkeyFromNpub(npub: string | null): string | null {
 
 export async function loadChat(): Promise<ChatMessage[]> {
   const snapshot = await fetchChat();
-  reactionCache = snapshot.reactions;
-  return snapshot.messages.sort((a, b) => a.createdAt - b.createdAt);
+  reactionCache = await Promise.all(snapshot.reactions.map(decryptReaction));
+  return (await Promise.all(snapshot.messages.map(decryptMessage))).sort((a, b) => a.createdAt - b.createdAt);
 }
 
 export async function loadReactions(messageIds: string[]): Promise<ChatReaction[]> {
   const wanted = new Set(messageIds);
-  if (!reactionCache.length) reactionCache = (await fetchChat()).reactions;
+  if (!reactionCache.length) reactionCache = await Promise.all((await fetchChat()).reactions.map(decryptReaction));
   return reactionCache.filter((r) => wanted.has(r.messageId));
 }
 
@@ -73,12 +74,12 @@ export function subscribeChat(
     for (const message of snapshot.messages) {
       if (seenMessages.has(message.id)) continue;
       seenMessages.add(message.id);
-      onMessage(message);
+      onMessage(await decryptMessage(message));
     }
     for (const reaction of snapshot.reactions) {
       if (seenReactions.has(reaction.id)) continue;
       seenReactions.add(reaction.id);
-      onReaction?.(reaction);
+      onReaction?.(await decryptReaction(reaction));
     }
   }
 
@@ -95,18 +96,22 @@ export function subscribeChat(
   };
 }
 
-export function sendChat(
+export async function sendChat(
   content: string,
   replyTo?: { id: string; pubkey: string },
 ): Promise<ChatMessage> {
-  return postChatMessage({
-    content,
+  const encrypted = await encryptPayload(content);
+  const message = await postChatMessage({
+    content: encrypted,
     ...(replyTo ? { replyToId: replyTo.id, replyToPubkey: replyTo.pubkey } : {}),
   });
+  return { ...message, content };
 }
 
-export function sendReaction(message: ChatMessage, content: string): Promise<ChatReaction> {
-  return postChatReaction({ messageId: message.id, content });
+export async function sendReaction(message: ChatMessage, content: string): Promise<ChatReaction> {
+  const encrypted = await encryptPayload(content);
+  const reaction = await postChatReaction({ messageId: message.id, content: encrypted });
+  return { ...reaction, content };
 }
 
 export async function loadProfiles(pubkeys: string[]): Promise<Record<string, ChatProfile>> {
@@ -137,3 +142,63 @@ export async function loadProfiles(pubkeys: string[]): Promise<Record<string, Ch
 export function shortPubkey(pubkey: string): string {
   return `${pubkey.slice(0, 8)}:${pubkey.slice(-4)}`;
 }
+
+type EncryptedEnvelope = {
+  v: 1;
+  alg: "nip44";
+  room: "gashboard-chat";
+  recipients: Array<{ pubkey: string; ciphertext: string }>;
+};
+
+async function encryptPayload(plaintext: string): Promise<string> {
+  const signer = getActiveSigner();
+  if (!signer) throw new Error("Reconnect your signer to encrypt private chat");
+  const recipients = await getRecipients();
+  try {
+    const encrypted = await Promise.all(
+      recipients.map(async (pubkey) => ({
+        pubkey,
+        ciphertext: await signer.encrypt(pubkey, plaintext),
+      })),
+    );
+    return JSON.stringify({ v: 1, alg: "nip44", room: "gashboard-chat", recipients: encrypted } satisfies EncryptedEnvelope);
+  } catch (e) {
+    throw new Error(
+      e instanceof Error
+        ? `Private chat encryption failed: ${e.message}. Reconnect signer and approve NIP-44 encryption.`
+        : "Private chat encryption failed. Reconnect signer and approve NIP-44 encryption.",
+    );
+  }
+}
+
+async function decryptPayload(value: string, senderPubkey: string): Promise<string> {
+  const signer = getActiveSigner();
+  if (!signer) return "[encrypted - reconnect signer]";
+  try {
+    const own = await signer.getPublicKey();
+    const envelope = JSON.parse(value) as EncryptedEnvelope;
+    if (envelope.v !== 1 || envelope.alg !== "nip44" || envelope.room !== "gashboard-chat") {
+      return "[encrypted with unknown chat format]";
+    }
+    const item = envelope.recipients.find((r) => r.pubkey === own);
+    if (!item) return "[encrypted for another recipient]";
+    return await signer.decrypt(senderPubkey, item.ciphertext);
+  } catch {
+    return "[encrypted - decrypt failed]";
+  }
+}
+
+async function decryptMessage(message: ChatMessage): Promise<ChatMessage> {
+  return { ...message, content: await decryptPayload(message.content, message.pubkey) };
+}
+
+async function decryptReaction(reaction: ChatReaction): Promise<ChatReaction> {
+  return { ...reaction, content: await decryptPayload(reaction.content, reaction.pubkey) };
+}
+
+async function getRecipients(): Promise<string[]> {
+  const signer = getActiveSigner();
+  const own = await signer?.getPublicKey();
+  if (!cachedRecipients) cachedRecipients = await fetchChatPubkeys();
+  return [...new Set([...(cachedRecipients ?? []), ...(own ? [own] : [])])].filter(Boolean);
+}