From 56f2c1807c27e4cd4a8725e6635c86cd122a7dc6 Mon Sep 17 00:00:00 2001
From: thePR0M3TH3AN <53631862+PR0M3TH3AN@users.noreply.github.com>
Date: Mon, 19 Jan 2026 08:39:43 -0500
Subject: [PATCH] Implement worker-based NIP-04 DM sending

---
 js/nostr/client.js              | 255 ++++++++++++++++++++++----------
 js/nostr/nip04Worker.js         |  91 ++++++++++++
 js/nostr/nip04WorkerClient.js   | 108 ++++++++++++++
 js/storage/dmDb.js              |   8 +
 js/ui/profileModalController.js |   2 +-
 5 files changed, 388 insertions(+), 76 deletions(-)
 create mode 100644 js/nostr/nip04Worker.js
 create mode 100644 js/nostr/nip04WorkerClient.js

diff --git a/js/nostr/client.js b/js/nostr/client.js
index 9a263105..f58721c7 100644
--- a/js/nostr/client.js
+++ b/js/nostr/client.js
@@ -106,7 +106,9 @@ import {
   resolveSimplePoolConstructor,
   shimLegacySimplePoolMethods,
 } from "./toolkit.js";
+import { encryptNip04InWorker } from "./nip04WorkerClient.js";
 import { devLogger, userLogger } from "../utils/logger.js";
+import { updateConversationFromMessage, writeMessages } from "../storage/dmDb.js";
 import {
   DEFAULT_NIP07_ENCRYPTION_METHODS,
   DEFAULT_NIP07_PERMISSION_METHODS,
@@ -4324,7 +4326,14 @@ export class NostrClient {
     return newPromise;
   }
 
-  async sendDirectMessage(targetNpub, message, actorPubkeyOverride = null) {
+  async sendDirectMessage(targetNpub, message, actorPubkeyOverride = null, options = {}) {
+    let resolvedOptions = options;
+    let resolvedActorOverride = actorPubkeyOverride;
+    if (actorPubkeyOverride && typeof actorPubkeyOverride === "object") {
+      resolvedOptions = actorPubkeyOverride;
+      resolvedActorOverride = null;
+    }
+
     const trimmedTarget = typeof targetNpub === "string" ? targetNpub.trim() : "";
     const trimmedMessage = typeof message === "string" ? message.trim() : "";
 
@@ -4341,12 +4350,12 @@ export class NostrClient {
     }
 
     const activeSignerCandidate =
-      typeof actorPubkeyOverride === "string" && actorPubkeyOverride.trim()
-        ? resolveActiveSigner(actorPubkeyOverride)
+      typeof resolvedActorOverride === "string" && resolvedActorOverride.trim()
+        ? resolveActiveSigner(resolvedActorOverride)
         : resolveActiveSigner(this.pubkey);
     const baseActiveSigner = activeSignerCandidate || getActiveSigner();
     const signer =
-      typeof actorPubkeyOverride === "string" && actorPubkeyOverride.trim()
+      typeof resolvedActorOverride === "string" && resolvedActorOverride.trim()
         ? activeSignerCandidate
         : baseActiveSigner
         ? resolveActiveSigner(baseActiveSigner.pubkey || this.pubkey)
@@ -4374,8 +4383,8 @@ export class NostrClient {
     }
 
     let actorHex =
-      typeof actorPubkeyOverride === "string" && actorPubkeyOverride.trim()
-        ? actorPubkeyOverride.trim()
+      typeof resolvedActorOverride === "string" && resolvedActorOverride.trim()
+        ? resolvedActorOverride.trim()
         : "";
 
     if (!actorHex && typeof this.pubkey === "string") {
@@ -4386,67 +4395,87 @@ export class NostrClient {
       actorHex = signer.pubkey;
     }
 
-    if (!actorHex) {
-      return { ok: false, error: "missing-actor-pubkey" };
-    }
-
     const targetHex = decodeNpubToHex(trimmedTarget);
     if (!targetHex) {
       return { ok: false, error: "invalid-target" };
     }
 
-    const encryptionCandidates = [];
-    const signerCapabilities = resolveSignerCapabilities(signer);
-    const allowNip04Fallback = signerCapabilities.nip04 === true;
-    if (
-      signerCapabilities.nip44 &&
-      typeof signer.nip44Encrypt === "function"
-    ) {
-      encryptionCandidates.push({
-        scheme: "nip44",
-        encrypt: signer.nip44Encrypt,
-      });
-    }
-    if (
-      signerCapabilities.nip04 &&
-      typeof signer.nip04Encrypt === "function"
-    ) {
-      encryptionCandidates.push({
-        scheme: "nip04",
-        encrypt: signer.nip04Encrypt,
-      });
+    const signingAdapter =
+      resolvedOptions?.signingAdapter &&
+      typeof resolvedOptions.signingAdapter === "object"
+        ? resolvedOptions.signingAdapter
+        : signer && typeof signer.signEvent === "function"
+        ? {
+            signEvent: (event) => signer.signEvent(event),
+            getPubkey: async () => actorHex || signer.pubkey || "",
+            getDisplayName: async () => "",
+          }
+        : null;
+
+    if (!signingAdapter || typeof signingAdapter.signEvent !== "function") {
+      return { ok: false, error: "sign-event-unavailable" };
     }
 
+    if (typeof signingAdapter.getPubkey === "function") {
+      try {
+        const adapterPubkey = await signingAdapter.getPubkey();
+        if (typeof adapterPubkey === "string" && adapterPubkey.trim()) {
+          actorHex = adapterPubkey.trim();
+        }
+      } catch (error) {
+        devLogger.warn("[nostr] Failed to resolve DM pubkey from adapter.", error);
+      }
+    }
+
+    if (!actorHex) {
+      return { ok: false, error: "missing-actor-pubkey" };
+    }
+
+    const signerCapabilities = resolveSignerCapabilities(signer);
     const encryptionErrors = [];
     let ciphertext = "";
 
-    for (const candidate of encryptionCandidates) {
+    const normalizedActorHex = normalizeActorKey(actorHex);
+    const sessionActor = this.sessionActor;
+    const sessionPrivateKey =
+      sessionActor &&
+      typeof sessionActor.pubkey === "string" &&
+      sessionActor.pubkey.toLowerCase() === normalizedActorHex &&
+      typeof sessionActor.privateKey === "string"
+        ? sessionActor.privateKey
+        : "";
+
+    if (sessionPrivateKey) {
       try {
-        const encrypted = await candidate.encrypt(targetHex, trimmedMessage);
+        ciphertext = await encryptNip04InWorker({
+          privateKey: sessionPrivateKey,
+          targetPubkey: targetHex,
+          plaintext: trimmedMessage,
+        });
+      } catch (error) {
+        encryptionErrors.push({ scheme: "nip04-worker", error });
+      }
+    }
+
+    if (
+      !ciphertext &&
+      signerCapabilities.nip04 &&
+      typeof signer.nip04Encrypt === "function"
+    ) {
+      try {
+        const encrypted = await signer.nip04Encrypt(targetHex, trimmedMessage);
         if (typeof encrypted === "string" && encrypted) {
           ciphertext = encrypted;
-          break;
         }
       } catch (error) {
-        encryptionErrors.push({ scheme: candidate.scheme, error });
+        encryptionErrors.push({ scheme: "nip04", error });
       }
     }
 
     if (!ciphertext) {
-      const normalizedActorHex = normalizeActorKey(actorHex);
-      const sessionActor = this.sessionActor;
-      const sessionMatchesActor =
-        sessionActor &&
-        typeof sessionActor.pubkey === "string" &&
-        sessionActor.pubkey.toLowerCase() === normalizedActorHex &&
-        typeof sessionActor.privateKey === "string" &&
-        sessionActor.privateKey;
-
-      const canFallbackWithSession = sessionMatchesActor && allowNip04Fallback;
-
-      if (!encryptionCandidates.length && !canFallbackWithSession) {
+      if (!sessionPrivateKey && !signerCapabilities.nip04) {
         const error = new Error(
-          "Your signer does not support NIP-44 or NIP-04 encryption.",
+          "Your signer does not support NIP-04 encryption.",
         );
         userLogger.warn("[nostr] Encryption unsupported for DM send.", error);
         return {
@@ -4456,31 +4485,6 @@ export class NostrClient {
         };
       }
 
-      if (canFallbackWithSession) {
-        try {
-          const tools = (await ensureNostrTools()) || getCachedNostrTools();
-          if (tools?.nip04 && typeof tools.nip04.encrypt === "function") {
-            const encrypted = await tools.nip04.encrypt(
-              sessionActor.privateKey,
-              targetHex,
-              trimmedMessage,
-            );
-            if (typeof encrypted === "string" && encrypted) {
-              ciphertext = encrypted;
-            }
-          } else {
-            encryptionErrors.push({
-              scheme: "nip04",
-              error: new Error("nostr-tools nip04 helpers unavailable"),
-            });
-          }
-        } catch (error) {
-          encryptionErrors.push({ scheme: "nip04", error });
-        }
-      }
-    }
-
-    if (!ciphertext) {
       const details =
         encryptionErrors.length === 1
           ? encryptionErrors[0].error
@@ -4501,13 +4505,103 @@ export class NostrClient {
 
     let signedEvent;
     try {
-      signedEvent = await queueSignEvent(signer, event);
+      signedEvent = await signingAdapter.signEvent(event);
     } catch (error) {
       return { ok: false, error: "signature-failed", details: error };
     }
 
-    const relays =
-      Array.isArray(this.relays) && this.relays.length ? this.relays : RELAY_URLS;
+    if (!signedEvent || typeof signedEvent.id !== "string") {
+      return { ok: false, error: "signature-failed" };
+    }
+
+    const conversationId = `dm:${[actorHex, targetHex].sort().join(":")}`;
+    const dmRecord = {
+      id: signedEvent.id,
+      conversation_id: conversationId,
+      sender_pubkey: actorHex,
+      receiver_pubkey: targetHex,
+      created_at: event.created_at,
+      kind: event.kind,
+      content: trimmedMessage,
+      tags: event.tags,
+      status: "pending",
+      seen: true,
+    };
+
+    try {
+      await writeMessages(dmRecord);
+      await updateConversationFromMessage(dmRecord, {
+        preview: trimmedMessage,
+        unseenDelta: 0,
+      });
+    } catch (error) {
+      devLogger.warn("[nostr] Failed to persist outgoing DM.", error);
+    }
+
+    const relayListCandidates = sanitizeRelayList(
+      Array.isArray(this.readRelays) && this.readRelays.length
+        ? this.readRelays
+        : Array.isArray(this.relays) && this.relays.length
+        ? this.relays
+        : RELAY_URLS,
+    );
+
+    const parseRecipientRelays = (relayEvent) => {
+      const tags = Array.isArray(relayEvent?.tags) ? relayEvent.tags : [];
+      const seen = new Set();
+      const candidates = [];
+
+      tags.forEach((tag) => {
+        if (!Array.isArray(tag) || tag[0] !== "r") {
+          return;
+        }
+        const url = typeof tag[1] === "string" ? tag[1].trim() : "";
+        if (!url) {
+          return;
+        }
+        const marker =
+          typeof tag[2] === "string" ? tag[2].trim().toLowerCase() : "";
+        if (marker === "write") {
+          return;
+        }
+        if (!seen.has(url)) {
+          seen.add(url);
+          candidates.push(url);
+        }
+      });
+
+      return sanitizeRelayList(candidates);
+    };
+
+    let recipientRelays = [];
+    if (relayListCandidates.length) {
+      try {
+        await this.ensurePool();
+        const events = await this.pool.list(relayListCandidates, [
+          { kinds: [10002], authors: [targetHex], limit: 1 },
+        ]);
+        const sorted = Array.isArray(events)
+          ? events
+              .filter((entry) => entry && entry.pubkey === targetHex)
+              .sort((a, b) => (b?.created_at || 0) - (a?.created_at || 0))
+          : [];
+        if (sorted.length) {
+          recipientRelays = parseRecipientRelays(sorted[0]);
+        }
+      } catch (error) {
+        devLogger.warn("[nostr] Failed to load recipient relay list.", error);
+      }
+    }
+
+    const fallbackRelays = sanitizeRelayList(
+      Array.isArray(this.writeRelays) && this.writeRelays.length
+        ? this.writeRelays
+        : Array.isArray(this.relays) && this.relays.length
+        ? this.relays
+        : RELAY_URLS,
+    );
+
+    const relays = recipientRelays.length ? recipientRelays : fallbackRelays;
 
     const publishResults = await Promise.all(
       relays.map((url) => publishEventToRelay(this.pool, url, signedEvent))
@@ -4515,6 +4609,11 @@ export class NostrClient {
 
     const success = publishResults.some((result) => result.success);
     if (!success) {
+      try {
+        await writeMessages({ ...dmRecord, status: "failed" });
+      } catch (error) {
+        devLogger.warn("[nostr] Failed to persist DM failure state.", error);
+      }
       return {
         ok: false,
         error: "publish-failed",
@@ -4522,6 +4621,12 @@ export class NostrClient {
       };
     }
 
+    try {
+      await writeMessages({ ...dmRecord, status: "published" });
+    } catch (error) {
+      devLogger.warn("[nostr] Failed to persist DM publish state.", error);
+    }
+
     return { ok: true };
   }
 
diff --git a/js/nostr/nip04Worker.js b/js/nostr/nip04Worker.js
new file mode 100644
index 00000000..942d7169
--- /dev/null
+++ b/js/nostr/nip04Worker.js
@@ -0,0 +1,91 @@
+import { ensureNostrTools, getCachedNostrTools } from "./toolkit.js";
+import { devLogger } from "../utils/logger.js";
+
+const workerScope = typeof self !== "undefined" ? self : null;
+
+const postResponse = (payload) => {
+  if (!workerScope || typeof workerScope.postMessage !== "function") {
+    return;
+  }
+  workerScope.postMessage(payload);
+};
+
+const ensureNip04 = async () => {
+  const tools = (await ensureNostrTools()) || getCachedNostrTools();
+  const nip04 = tools?.nip04;
+  if (!nip04 || typeof nip04.encrypt !== "function") {
+    throw new Error("nip04-unavailable");
+  }
+  return nip04;
+};
+
+const normalizePayload = (payload) => {
+  if (!payload || typeof payload !== "object") {
+    return null;
+  }
+
+  const id =
+    typeof payload.id === "string" || typeof payload.id === "number"
+      ? payload.id
+      : null;
+  const privateKey =
+    typeof payload.privateKey === "string" ? payload.privateKey.trim() : "";
+  const targetPubkey =
+    typeof payload.targetPubkey === "string" ? payload.targetPubkey.trim() : "";
+  const plaintext =
+    typeof payload.plaintext === "string" ? payload.plaintext : "";
+
+  if (!id || !privateKey || !targetPubkey) {
+    return null;
+  }
+
+  return {
+    id,
+    privateKey,
+    targetPubkey,
+    plaintext,
+  };
+};
+
+const handleMessage = async (event) => {
+  const payload = normalizePayload(event?.data);
+  if (!payload) {
+    postResponse({
+      id: event?.data?.id ?? null,
+      ok: false,
+      error: { message: "invalid-payload" },
+    });
+    return;
+  }
+
+  try {
+    const nip04 = await ensureNip04();
+    const ciphertext = await nip04.encrypt(
+      payload.privateKey,
+      payload.targetPubkey,
+      payload.plaintext,
+    );
+
+    postResponse({
+      id: payload.id,
+      ok: true,
+      ciphertext,
+    });
+  } catch (error) {
+    devLogger.warn("[nip04Worker] Encryption failed", error);
+    postResponse({
+      id: payload.id,
+      ok: false,
+      error: {
+        message: error?.message || "nip04-worker-failed",
+        name: error?.name || "Error",
+      },
+    });
+  }
+};
+
+if (workerScope?.addEventListener) {
+  workerScope.addEventListener("message", (event) => {
+    void handleMessage(event);
+  });
+}
diff --git a/js/nostr/nip04WorkerClient.js b/js/nostr/nip04WorkerClient.js
new file mode 100644
index 00000000..9d6e0c8b
--- /dev/null
+++ b/js/nostr/nip04WorkerClient.js
@@ -0,0 +1,108 @@
+import { devLogger } from "../utils/logger.js";
+
+const DEFAULT_TIMEOUT_MS = 12000;
+
+let workerInstance = null;
+let workerReady = false;
+let requestId = 0;
+const pending = new Map();
+
+function attachWorkerListeners(worker) {
+  if (!worker || workerReady) {
+    return;
+  }
+
+  worker.addEventListener("message", (event) => {
+    const data = event?.data || {};
+    const id = data.id;
+    if (!pending.has(id)) {
+      return;
+    }
+
+    const entry = pending.get(id);
+    pending.delete(id);
+    clearTimeout(entry.timeoutId);
+
+    if (data.ok && typeof data.ciphertext === "string") {
+      entry.resolve(data.ciphertext);
+      return;
+    }
+
+    const message = data?.error?.message || "nip04-worker-error";
+    const error = new Error(message);
+    error.name = data?.error?.name || "Error";
+    entry.reject(error);
+  });
+
+  worker.addEventListener("error", (error) => {
+    devLogger.warn("[nip04WorkerClient] Worker error", error);
+    for (const entry of pending.values()) {
+      clearTimeout(entry.timeoutId);
+      entry.reject(error instanceof Error ? error : new Error("nip04-worker-error"));
+    }
+    pending.clear();
+  });
+
+  workerReady = true;
+}
+
+function ensureWorker() {
+  if (workerInstance) {
+    return workerInstance;
+  }
+
+  if (typeof Worker === "undefined") {
+    return null;
+  }
+
+  try {
+    workerInstance = new Worker(new URL("./nip04Worker.js", import.meta.url), {
+      type: "module",
+    });
+    attachWorkerListeners(workerInstance);
+  } catch (error) {
+    devLogger.warn("[nip04WorkerClient] Failed to create worker", error);
+    workerInstance = null;
+  }
+
+  return workerInstance;
+}
+
+export function encryptNip04InWorker({
+  privateKey,
+  targetPubkey,
+  plaintext,
+  timeoutMs = DEFAULT_TIMEOUT_MS,
+} = {}) {
+  const worker = ensureWorker();
+  if (!worker) {
+    return Promise.reject(new Error("nip04-worker-unavailable"));
+  }
+
+  const trimmedPrivateKey =
+    typeof privateKey === "string" ? privateKey.trim() : "";
+  const trimmedTarget =
+    typeof targetPubkey === "string" ? targetPubkey.trim() : "";
+  const message = typeof plaintext === "string" ? plaintext : "";
+
+  if (!trimmedPrivateKey || !trimmedTarget) {
+    return Promise.reject(new Error("nip04-worker-invalid-input"));
+  }
+
+  const id = `${Date.now()}-${requestId++}`;
+
+  return new Promise((resolve, reject) => {
+    const timeoutId = setTimeout(() => {
+      pending.delete(id);
+      reject(new Error("nip04-worker-timeout"));
+    }, timeoutMs);
+
+    pending.set(id, { resolve, reject, timeoutId });
+    worker.postMessage({
+      id,
+      privateKey: trimmedPrivateKey,
+      targetPubkey: trimmedTarget,
+      plaintext: message,
+    });
+  });
+}
diff --git a/js/storage/dmDb.js b/js/storage/dmDb.js
index 8ec1e875..7b1cc322 100644
--- a/js/storage/dmDb.js
+++ b/js/storage/dmDb.js
@@ -135,6 +135,12 @@ function normalizeMessage(raw) {
   const receiverPubkey = normalizePubkey(
     raw.receiver_pubkey ?? raw.receiverPubkey ?? raw.to_pubkey,
   );
+  const statusRaw = typeof raw.status === "string" ? raw.status.trim() : "";
+  const status =
+    statusRaw === "pending" || statusRaw === "published" || statusRaw === "failed"
+      ? statusRaw
+      : "";
+  const seen = raw.seen === true;
 
   return {
     id,
@@ -146,6 +152,8 @@ function normalizeMessage(raw) {
     content: typeof raw.content === "string" ? raw.content : "",
     tags: Array.isArray(raw.tags) ? raw.tags : [],
     relay: typeof raw.relay === "string" ? raw.relay : "",
+    status,
+    seen,
   };
 }
 
diff --git a/js/ui/profileModalController.js b/js/ui/profileModalController.js
index e7fd360f..1de8b9b7 100644
--- a/js/ui/profileModalController.js
+++ b/js/ui/profileModalController.js
@@ -2085,7 +2085,7 @@ export class ProfileModalController {
       case "sign-event-unavailable":
         return "Connect a Nostr signer to send messages.";
       case "encryption-unsupported":
-        return "Your signer does not support NIP-44 or NIP-04 encryption.";
+        return "Your signer does not support NIP-04 encryption.";
       case "extension-permission-denied":
         return "Please grant your Nostr extension permission to send messages.";
       case "missing-actor-pubkey":