diff --git a/src/channels/discord.ts b/src/channels/discord.ts
index 1abc7cf..77d5121 100644
--- a/src/channels/discord.ts
+++ b/src/channels/discord.ts
@@ -350,8 +350,14 @@ Ask the bot owner to approve with:
       throw new Error(`Discord channel not found or not text-based: ${msg.chatId}`);
     }
 
-    const result = await (channel as { send: (content: string) => Promise<{ id: string }> }).send(msg.text);
-    return { messageId: result.id };
+    const sendable = channel as { send: (content: string) => Promise<{ id: string }> };
+    const chunks = splitMessageText(msg.text);
+    let lastMessageId = '';
+    for (const chunk of chunks) {
+      const result = await sendable.send(chunk);
+      lastMessageId = result.id;
+    }
+    return { messageId: lastMessageId };
   }
 
   async sendFile(file: OutboundFile): Promise<{ messageId: string }> {
@@ -384,7 +390,12 @@ Ask the bot owner to approve with:
       log.warn('Cannot edit message not sent by bot');
       return;
     }
-    await message.edit(text);
+
+    // Discord edit limit is 2000 chars -- truncate if needed (edits can't split)
+    const truncated = text.length > DISCORD_MAX_LENGTH
+      ? text.slice(0, DISCORD_MAX_LENGTH - 1) + '\u2026'
+      : text;
+    await message.edit(truncated);
   }
 
   async addReaction(chatId: string, messageId: string, emoji: string): Promise<void> {
@@ -559,6 +570,58 @@ function resolveDiscordEmoji(input: string): string {
   return input;
 }
 
+// Discord message length limit
+const DISCORD_MAX_LENGTH = 2000;
+// Leave some headroom when choosing split points
+const DISCORD_SPLIT_THRESHOLD = 1900;
+
+/**
+ * Split text into chunks that fit within Discord's 2000-char limit.
+ * Splits at paragraph boundaries (double newlines), falling back to
+ * single newlines, then hard-splitting at the threshold.
+ */
+function splitMessageText(text: string): string[] {
+  if (text.length <= DISCORD_SPLIT_THRESHOLD) {
+    return [text];
+  }
+
+  const chunks: string[] = [];
+  let remaining = text;
+
+  while (remaining.length > DISCORD_SPLIT_THRESHOLD) {
+    let splitIdx = -1;
+
+    const searchRegion = remaining.slice(0, DISCORD_SPLIT_THRESHOLD);
+    // Try paragraph boundary (double newline)
+    const lastParagraph = searchRegion.lastIndexOf('\n\n');
+    if (lastParagraph > DISCORD_SPLIT_THRESHOLD * 0.3) {
+      splitIdx = lastParagraph;
+    }
+
+    // Fall back to single newline
+    if (splitIdx === -1) {
+      const lastNewline = searchRegion.lastIndexOf('\n');
+      if (lastNewline > DISCORD_SPLIT_THRESHOLD * 0.3) {
+        splitIdx = lastNewline;
+      }
+    }
+
+    // Hard split as last resort
+    if (splitIdx === -1) {
+      splitIdx = DISCORD_SPLIT_THRESHOLD;
+    }
+
+    chunks.push(remaining.slice(0, splitIdx).trimEnd());
+    remaining = remaining.slice(splitIdx).trimStart();
+  }
+
+  if (remaining.trim()) {
+    chunks.push(remaining.trim());
+  }
+
+  return chunks;
+}
+
 type DiscordAttachment = {
   id?: string;
   name?: string | null;
diff --git a/src/core/bot.ts b/src/core/bot.ts
index 2ae7fa5..e20e932 100644
--- a/src/core/bot.ts
+++ b/src/core/bot.ts
@@ -1024,8 +1024,13 @@ export class LettaBot implements AgentSession {
               await adapter.sendMessage({ chatId: msg.chatId, text: prefixed, threadId: msg.threadId });
             }
             sentAnyMessage = true;
-          } catch {
-            if (messageId) sentAnyMessage = true;
+          } catch (finalizeErr) {
+            if (messageId) {
+              // Edit failed but original message was already visible
+              sentAnyMessage = true;
+            } else {
+              log.warn('finalizeMessage send failed:', finalizeErr instanceof Error ? finalizeErr.message : finalizeErr);
+            }
           }
         }
         response = '';
@@ -1442,8 +1447,9 @@ export class LettaBot implements AgentSession {
           }
           sentAnyMessage = true;
           this.store.resetRecoveryAttempts();
-        } catch {
+        } catch (sendErr) {
           // Edit failed -- send as new message so user isn't left with truncated text
+          log.warn('Final message delivery failed:', sendErr instanceof Error ? sendErr.message : sendErr);
           try {
             await adapter.sendMessage({ chatId: msg.chatId, text: prefixedFinal, threadId: msg.threadId });
             sentAnyMessage = true;