diff --git a/src/discord/send.outbound.ts b/src/discord/send.outbound.ts
index a47d0f4f1..22b402ae3 100644
--- a/src/discord/send.outbound.ts
+++ b/src/discord/send.outbound.ts
@@ -13,7 +13,7 @@ import {
   createDiscordClient,
   normalizeDiscordPollInput,
   normalizeStickerIds,
-  parseRecipient,
+  parseAndResolveRecipient,
   resolveChannelId,
   sendDiscordMedia,
   sendDiscordText,
@@ -49,7 +49,7 @@ export async function sendMessageDiscord(
   const chunkMode = resolveChunkMode(cfg, "discord", accountInfo.accountId);
   const textWithTables = convertMarkdownTables(text ?? "", tableMode);
   const { token, rest, request } = createDiscordClient(opts, cfg);
-  const recipient = parseRecipient(to);
+  const recipient = await parseAndResolveRecipient(to, opts.accountId);
   const { channelId } = await resolveChannelId(rest, recipient, request);
   let result: { id: string; channel_id: string } | { id: string | null; channel_id: string };
   try {
@@ -104,7 +104,7 @@ export async function sendStickerDiscord(
 ): Promise<DiscordSendResult> {
   const cfg = loadConfig();
   const { rest, request } = createDiscordClient(opts, cfg);
-  const recipient = parseRecipient(to);
+  const recipient = await parseAndResolveRecipient(to, opts.accountId);
   const { channelId } = await resolveChannelId(rest, recipient, request);
   const content = opts.content?.trim();
   const stickers = normalizeStickerIds(stickerIds);
@@ -131,7 +131,7 @@ export async function sendPollDiscord(
 ): Promise<DiscordSendResult> {
   const cfg = loadConfig();
   const { rest, request } = createDiscordClient(opts, cfg);
-  const recipient = parseRecipient(to);
+  const recipient = await parseAndResolveRecipient(to, opts.accountId);
   const { channelId } = await resolveChannelId(rest, recipient, request);
   const content = opts.content?.trim();
   const payload = normalizeDiscordPollInput(poll);
diff --git a/src/discord/send.shared.ts b/src/discord/send.shared.ts
index 4919be29d..1cf2a93a9 100644
--- a/src/discord/send.shared.ts
+++ b/src/discord/send.shared.ts
@@ -13,7 +13,7 @@ import type { ChunkMode } from "../auto-reply/chunk.js";
 import { chunkDiscordTextWithMode } from "./chunk.js";
 import { fetchChannelPermissionsDiscord, isThreadChannelType } from "./send.permissions.js";
 import { DiscordSendError } from "./send.types.js";
-import { parseDiscordTarget } from "./targets.js";
+import { parseDiscordTarget, resolveDiscordTarget } from "./targets.js";
 import { normalizeDiscordToken } from "./token.js";
 
 const DISCORD_TEXT_LIMIT = 2000;
@@ -101,6 +101,44 @@ function parseRecipient(raw: string): DiscordRecipient {
   return { kind: target.kind, id: target.id };
 }
 
+/**
+ * Parse and resolve Discord recipient, including username lookup.
+ * This enables sending DMs by username (e.g., "john.doe") by querying
+ * the Discord directory to resolve usernames to user IDs.
+ *
+ * @param raw - The recipient string (username, ID, or known format)
+ * @param accountId - Discord account ID to use for directory lookup
+ * @returns Parsed DiscordRecipient with resolved user ID if applicable
+ */
+export async function parseAndResolveRecipient(
+  raw: string,
+  accountId?: string,
+): Promise<DiscordRecipient> {
+  const cfg = loadConfig();
+  const accountInfo = resolveDiscordAccount({ cfg, accountId });
+
+  // First try to resolve using directory lookup (handles usernames)
+  const resolved = await resolveDiscordTarget(raw, {
+    cfg,
+    accountId: accountInfo.accountId,
+  });
+
+  if (resolved) {
+    return { kind: resolved.kind, id: resolved.id };
+  }
+
+  // Fallback to standard parsing (for channels, etc.)
+  const parsed = parseDiscordTarget(raw, {
+    ambiguousMessage: `Ambiguous Discord recipient "${raw.trim()}". Use "user:${raw.trim()}" for DMs or "channel:${raw.trim()}" for channel messages.`,
+  });
+
+  if (!parsed) {
+    throw new Error("Recipient is required for Discord sends");
+  }
+
+  return { kind: parsed.kind, id: parsed.id };
+}
+
 function normalizeStickerIds(raw: string[]) {
   const ids = raw.map((entry) => entry.trim()).filter(Boolean);
   if (ids.length === 0) {
diff --git a/src/discord/targets.ts b/src/discord/targets.ts
index 3a3c93ec8..311955182 100644
--- a/src/discord/targets.ts
+++ b/src/discord/targets.ts
@@ -5,8 +5,13 @@ import {
   type MessagingTarget,
   type MessagingTargetKind,
   type MessagingTargetParseOptions,
+  type DirectoryConfigParams,
+  type ChannelDirectoryEntry,
 } from "../channels/targets.js";
 
+import { listDiscordDirectoryPeersLive } from "./directory-live.js";
+import { resolveDiscordAccount } from "./accounts.js";
+
 export type DiscordTargetKind = MessagingTargetKind;
 
 export type DiscordTarget = MessagingTarget;
@@ -60,3 +65,60 @@ export function resolveDiscordChannelId(raw: string): string {
   const target = parseDiscordTarget(raw, { defaultKind: "channel" });
   return requireTargetKind({ platform: "Discord", target, kind: "channel" });
 }
+
+/**
+ * Resolve a Discord username to user ID using the directory lookup.
+ * This enables sending DMs by username instead of requiring explicit user IDs.
+ *
+ * @param raw - The username or raw target string (e.g., "john.doe")
+ * @param options - Directory configuration params (cfg, accountId, limit)
+ * @returns Parsed MessagingTarget with user ID, or undefined if not found
+ */
+export async function resolveDiscordTarget(
+  raw: string,
+  options: DirectoryConfigParams,
+): Promise<MessagingTarget | undefined> {
+  const trimmed = raw.trim();
+  if (!trimmed) return undefined;
+
+  // If already a known format, parse directly
+  const directParse = parseDiscordTarget(trimmed, options);
+  if (directParse && directParse.kind !== "channel" && !isLikelyUsername(trimmed)) {
+    return directParse;
+  }
+
+  // Try to resolve as a username via directory lookup
+  try {
+    const directoryEntries = await listDiscordDirectoryPeersLive({
+      ...options,
+      query: trimmed,
+      limit: 1,
+    });
+
+    const match = directoryEntries[0];
+    if (match && match.kind === "user") {
+      // Extract user ID from the directory entry (format: "user:<id>")
+      const userId = match.id.replace(/^user:/, "");
+      return buildMessagingTarget("user", userId, trimmed);
+    }
+  } catch (error) {
+    // Directory lookup failed - fall through to parse as-is
+    // This preserves existing behavior for channel names
+  }
+
+  // Fallback to original parsing (for channels, etc.)
+  return parseDiscordTarget(trimmed, options);
+}
+
+/**
+ * Check if a string looks like a Discord username (not a mention, prefix, or ID).
+ * Usernames typically don't start with special characters except underscore.
+ */
+function isLikelyUsername(input: string): boolean {
+  // Skip if it's already a known format
+  if (/^(user:|channel:|discord:|@|<@!?)|[\d]+$/.test(input)) {
+    return false;
+  }
+  // Likely a username if it doesn't match known patterns
+  return true;
+}