diff --git a/js/nostr.js b/js/nostr.js
index 05b22ec3..1aa43fd5 100644
--- a/js/nostr.js
+++ b/js/nostr.js
@@ -2012,6 +2012,20 @@ class NostrClient {
       totalChunks: 1,
     };
 
+    const ciphertextRaw =
+      pointerEvent && typeof pointerEvent.content === "string"
+        ? pointerEvent.content
+        : "";
+    const ciphertext = ciphertextRaw.trim();
+
+    if (!isNip04EncryptedWatchHistoryEvent(pointerEvent, ciphertext)) {
+      return parseWatchHistoryContentWithFallback(
+        ciphertext,
+        fallbackItems,
+        fallbackPayload
+      );
+    }
+
     const normalizedActor =
       typeof actorPubkey === "string" && actorPubkey.trim()
         ? actorPubkey.trim().toLowerCase()
@@ -2020,11 +2034,6 @@ class NostrClient {
       return fallbackPayload;
     }
 
-    const ciphertext =
-      pointerEvent && typeof pointerEvent.content === "string"
-        ? pointerEvent.content.trim()
-        : "";
-
     if (!ciphertext) {
       return fallbackPayload;
     }
@@ -2042,11 +2051,11 @@ class NostrClient {
           normalizedActor,
           ciphertext
         );
-        const parsed = parseWatchHistoryPayload(plaintext);
-        if (parsed.items.length || fallbackItems.length === 0) {
-          return parsed;
-        }
-        return { ...parsed, items: fallbackItems };
+        return parseWatchHistoryContentWithFallback(
+          typeof plaintext === "string" ? plaintext.trim() : "",
+          fallbackItems,
+          fallbackPayload
+        );
       } catch (error) {
         if (isDevMode) {
           console.warn(
@@ -2078,11 +2087,11 @@ class NostrClient {
           normalizedActor,
           ciphertext
         );
-        const parsed = parseWatchHistoryPayload(plaintext);
-        if (parsed.items.length || fallbackItems.length === 0) {
-          return parsed;
-        }
-        return { ...parsed, items: fallbackItems };
+        return parseWatchHistoryContentWithFallback(
+          typeof plaintext === "string" ? plaintext.trim() : "",
+          fallbackItems,
+          fallbackPayload
+        );
       } catch (error) {
         if (isDevMode) {
           console.warn(
@@ -6021,6 +6030,114 @@ class NostrClient {
   }
 }
 
+function looksLikeJsonStructure(content) {
+  if (typeof content !== "string") {
+    return false;
+  }
+  const trimmed = content.trim();
+  if (!trimmed) {
+    return false;
+  }
+  const first = trimmed[0];
+  return first === "{" || first === "[";
+}
+
+function mergeWatchHistoryItemsWithFallback(parsed, fallbackItems) {
+  if (!parsed || typeof parsed !== "object") {
+    return {
+      version: 0,
+      items: fallbackItems,
+      snapshot: "",
+      chunkIndex: 0,
+      totalChunks: 1,
+    };
+  }
+
+  if (Array.isArray(parsed.items) && parsed.items.length) {
+    return parsed;
+  }
+
+  if (!Array.isArray(fallbackItems) || fallbackItems.length === 0) {
+    return parsed;
+  }
+
+  return { ...parsed, items: fallbackItems };
+}
+
+function parseWatchHistoryContentWithFallback(
+  content,
+  fallbackItems,
+  fallbackPayload
+) {
+  if (!looksLikeJsonStructure(content)) {
+    return fallbackPayload;
+  }
+
+  try {
+    JSON.parse(content);
+  } catch (error) {
+    return fallbackPayload;
+  }
+
+  const parsed = parseWatchHistoryPayload(content);
+  return mergeWatchHistoryItemsWithFallback(parsed, fallbackItems);
+}
+
+function isNip04EncryptedWatchHistoryEvent(pointerEvent, ciphertext) {
+  if (!pointerEvent || typeof pointerEvent !== "object") {
+    return false;
+  }
+
+  const tags = Array.isArray(pointerEvent.tags) ? pointerEvent.tags : [];
+  const normalizedCiphertext =
+    typeof ciphertext === "string" ? ciphertext.trim() : "";
+
+  if (!normalizedCiphertext) {
+    return false;
+  }
+
+  const hasEncryptionTag = tags.some((tag) => {
+    if (!Array.isArray(tag) || tag.length < 2) {
+      return false;
+    }
+    const label =
+      typeof tag[0] === "string" ? tag[0].trim().toLowerCase() : "";
+    if (label !== "encrypted") {
+      return false;
+    }
+    const value =
+      typeof tag[1] === "string" ? tag[1].trim().toLowerCase() : "";
+    return value === "nip04" || value === "nip-04";
+  });
+
+  if (hasEncryptionTag) {
+    return !looksLikeJsonStructure(normalizedCiphertext);
+  }
+
+  if (looksLikeJsonStructure(normalizedCiphertext)) {
+    return false;
+  }
+
+  const ivIndex = normalizedCiphertext.indexOf("?iv=");
+  const baseSegment =
+    ivIndex >= 0
+      ? normalizedCiphertext.slice(0, ivIndex)
+      : normalizedCiphertext;
+  const ivSegment =
+    ivIndex >= 0 ? normalizedCiphertext.slice(ivIndex + 4) : "";
+
+  const base64Regex = /^[A-Za-z0-9+/]+={0,2}$/;
+  if (!baseSegment || !base64Regex.test(baseSegment)) {
+    return false;
+  }
+
+  if (ivSegment && !base64Regex.test(ivSegment)) {
+    return false;
+  }
+
+  return true;
+}
+
 export const nostrClient = new NostrClient();
 
 export const recordVideoView = (...args) =>
diff --git a/tests/watch-history.test.mjs b/tests/watch-history.test.mjs
index f9e4f5d9..fb365ee3 100644
--- a/tests/watch-history.test.mjs
+++ b/tests/watch-history.test.mjs
@@ -1066,6 +1066,194 @@ try {
   Date.now = originalDateNow;
 }
 
+const plaintextPayload = {
+  version: 2,
+  snapshot: "plaintext-snapshot",
+  chunkIndex: 0,
+  totalChunks: 1,
+  items: [
+    {
+      type: "e",
+      value: "plaintext-pointer",
+      relay: "wss://relay.unit",
+      watchedAt: 1_700_000_123_000,
+    },
+  ],
+};
+
+const plaintextChunkEvent = {
+  kind: WATCH_HISTORY_KIND,
+  pubkey: ACTOR,
+  created_at: 333,
+  tags: [
+    ["d", `${WATCH_HISTORY_CHUNK_PREFIX}/plaintext/0`],
+    ["snapshot", plaintextPayload.snapshot],
+    ["chunk", String(plaintextPayload.chunkIndex), String(plaintextPayload.totalChunks)],
+    ["e", plaintextPayload.items[0].value, plaintextPayload.items[0].relay],
+  ],
+  content: JSON.stringify(plaintextPayload),
+};
+
+const originalWindowNostr = globalThis.window.nostr;
+if (!globalThis.window.NostrTools) {
+  globalThis.window.NostrTools = {};
+}
+if (!globalThis.window.NostrTools.nip04) {
+  globalThis.window.NostrTools.nip04 = {};
+}
+const originalSessionDecrypt = globalThis.window.NostrTools.nip04.decrypt;
+
+try {
+  globalThis.window.nostr = {
+    nip04: {
+      decrypt: () => {
+        throw new Error("plaintext chunk should not trigger extension decrypt");
+      },
+    },
+  };
+  globalThis.window.NostrTools.nip04.decrypt = () => {
+    throw new Error("plaintext chunk should not trigger session decrypt");
+  };
+
+  const plaintextClient = createDecryptClient(ACTOR);
+  const plaintextResult = await plaintextClient.decryptWatchHistoryEvent(
+    plaintextChunkEvent,
+    ACTOR
+  );
+
+  assert.deepEqual(
+    plaintextResult.items.map((item) => ({
+      type: item.type,
+      value: item.value,
+      relay: item.relay,
+      watchedAt: item.watchedAt,
+    })),
+    plaintextPayload.items,
+    "plaintext payload should be parsed without invoking nip04 helpers",
+  );
+  assert.equal(
+    plaintextResult.snapshot,
+    plaintextPayload.snapshot,
+    "plaintext payload should preserve snapshot metadata",
+  );
+  assert.equal(
+    plaintextResult.chunkIndex,
+    plaintextPayload.chunkIndex,
+    "plaintext payload should preserve chunk index",
+  );
+  assert.equal(
+    plaintextResult.totalChunks,
+    plaintextPayload.totalChunks,
+    "plaintext payload should preserve chunk count",
+  );
+} finally {
+  globalThis.window.nostr = originalWindowNostr;
+  if (originalSessionDecrypt === undefined) {
+    delete globalThis.window.NostrTools.nip04.decrypt;
+  } else {
+    globalThis.window.NostrTools.nip04.decrypt = originalSessionDecrypt;
+  }
+}
+
+const encryptedPayload = {
+  version: 2,
+  snapshot: "encrypted-snapshot",
+  chunkIndex: 0,
+  totalChunks: 1,
+  items: [
+    {
+      type: "e",
+      value: "encrypted-pointer",
+      relay: "wss://relay.unit",
+      watchedAt: 1_700_000_456_000,
+    },
+  ],
+};
+
+const encryptedCiphertext = "ZW5jcnlwdGVkQ29udGVudD9mb29iYXI=?iv=YWJjMTIz";
+
+const encryptedChunkEvent = {
+  kind: WATCH_HISTORY_KIND,
+  pubkey: ACTOR,
+  created_at: 444,
+  tags: [
+    ["d", `${WATCH_HISTORY_CHUNK_PREFIX}/encrypted/0`],
+    ["encrypted", "nip04"],
+    ["snapshot", encryptedPayload.snapshot],
+    ["chunk", String(encryptedPayload.chunkIndex), String(encryptedPayload.totalChunks)],
+    ["e", encryptedPayload.items[0].value, encryptedPayload.items[0].relay],
+  ],
+  content: encryptedCiphertext,
+};
+
+const encryptedClient = createDecryptClient(ACTOR);
+encryptedClient.pubkey = ACTOR;
+
+const priorWindowNostr = globalThis.window.nostr;
+const priorSessionDecrypt = globalThis.window.NostrTools.nip04.decrypt;
+let extensionDecryptCalls = 0;
+let sessionDecryptCalls = 0;
+
+try {
+  globalThis.window.nostr = {
+    nip04: {
+      decrypt: async (pubkey, ciphertext) => {
+        extensionDecryptCalls += 1;
+        assert.equal(pubkey, ACTOR, "extension decrypt should target the actor");
+        assert.equal(
+          ciphertext,
+          encryptedCiphertext,
+          "extension decrypt should receive the chunk ciphertext",
+        );
+        return JSON.stringify(encryptedPayload);
+      },
+    },
+  };
+
+  globalThis.window.NostrTools.nip04.decrypt = async () => {
+    sessionDecryptCalls += 1;
+    return JSON.stringify(encryptedPayload);
+  };
+
+  const decryptedResult = await encryptedClient.decryptWatchHistoryEvent(
+    encryptedChunkEvent,
+    ACTOR
+  );
+
+  assert.equal(
+    extensionDecryptCalls,
+    1,
+    "encrypted chunks should invoke extension nip04 decrypt",
+  );
+  assert.equal(
+    sessionDecryptCalls,
+    0,
+    "successful extension decrypt should skip session fallback",
+  );
+  assert.deepEqual(
+    decryptedResult.items.map((item) => ({
+      type: item.type,
+      value: item.value,
+      relay: item.relay,
+      watchedAt: item.watchedAt,
+    })),
+    encryptedPayload.items,
+    "encrypted payload should be reconstructed from decrypted content",
+  );
+  assert.equal(
+    decryptedResult.snapshot,
+    encryptedPayload.snapshot,
+    "encrypted payload should preserve snapshot metadata",
+  );
+} finally {
+  globalThis.window.nostr = priorWindowNostr;
+  if (priorSessionDecrypt === undefined) {
+    delete globalThis.window.NostrTools.nip04.decrypt;
+  } else {
+    globalThis.window.NostrTools.nip04.decrypt = priorSessionDecrypt;
+  }
+}
+
 const unsortedVideos = [
   { id: "alpha", watchHistory: { watchedAt: 1_700_000_000_500 } },
   { id: "bravo", watchHistory: { watchedAt: 1_700_000_010_000 } },