diff --git a/src/core/bot.ts b/src/core/bot.ts
index c08fa88..e932869 100644
--- a/src/core/bot.ts
+++ b/src/core/bot.ts
@@ -79,6 +79,13 @@ export class LettaBot {
         });
         return '⏰ Heartbeat triggered (silent mode - check server logs)';
       }
+      case 'reset': {
+        const oldConversationId = this.store.conversationId;
+        this.store.conversationId = null;
+        this.store.resetRecoveryAttempts();
+        console.log(`[Command] /reset - conversation cleared (was: ${oldConversationId})`);
+        return 'Conversation reset. Send a message to start a new conversation. (Agent memory is preserved.)';
+      }
       default:
         return null;
     }
diff --git a/src/core/commands.ts b/src/core/commands.ts
index 739d0c6..3ac5375 100644
--- a/src/core/commands.ts
+++ b/src/core/commands.ts
@@ -4,7 +4,7 @@
  * Shared command parsing and help text for all channels.
  */
 
-export const COMMANDS = ['status', 'heartbeat', 'help', 'start'] as const;
+export const COMMANDS = ['status', 'heartbeat', 'reset', 'help', 'start'] as const;
 export type Command = typeof COMMANDS[number];
 
 export const HELP_TEXT = `LettaBot - AI assistant with persistent memory
@@ -12,6 +12,7 @@ export const HELP_TEXT = `LettaBot - AI assistant with persistent memory
 Commands:
 /status - Show current status
 /heartbeat - Trigger heartbeat
+/reset - Reset conversation (keeps agent memory)
 /help - Show this message
 
 Just send a message to get started!`;
diff --git a/src/main.ts b/src/main.ts
index 6697259..0723be7 100644
--- a/src/main.ts
+++ b/src/main.ts
@@ -122,7 +122,7 @@ import { DiscordAdapter } from './channels/discord.js';
 import { CronService } from './cron/service.js';
 import { HeartbeatService } from './cron/heartbeat.js';
 import { PollingService } from './polling/service.js';
-import { agentExists, findAgentByName } from './tools/letta-api.js';
+import { agentExists, findAgentByName, ensureNoToolApprovals } from './tools/letta-api.js';
 // Skills are now installed to agent-scoped location after agent creation (see bot.ts)
 
 // Check if config exists (skip in Railway/Docker where env vars are used directly)
@@ -380,6 +380,14 @@ async function main() {
     console.log(`[Agent] No agent found - will create "${agentName}" on first message`);
   }
   
+  // Proactively disable tool approvals for headless operation
+  // Prevents stuck states from server-side requires_approval=true (SDK issue #25)
+  if (initialStatus.agentId) {
+    ensureNoToolApprovals(initialStatus.agentId).catch(err => {
+      console.warn('[Agent] Failed to check tool approvals:', err);
+    });
+  }
+  
   // Register enabled channels
   if (config.telegram.enabled) {
     const telegram = new TelegramAdapter({
diff --git a/src/tools/letta-api.ts b/src/tools/letta-api.ts
index 70923fc..0fa6b99 100644
--- a/src/tools/letta-api.ts
+++ b/src/tools/letta-api.ts
@@ -235,20 +235,46 @@ export async function getPendingApprovals(
     const client = getClient();
 
     // Prefer agent-level pending approval to avoid scanning stale history.
+    // IMPORTANT: Must include 'agent.pending_approval' or the field won't be returned.
     try {
-      const agentState = await client.agents.retrieve(agentId);
+      const agentState = await client.agents.retrieve(agentId, {
+        include: ['agent.pending_approval'],
+      });
       if ('pending_approval' in agentState) {
-        const pending = (agentState as { pending_approval?: { id: string; run_id?: string | null; tool_calls?: Array<{ tool_call_id: string; name: string }>; tool_call?: { tool_call_id: string; name: string } } | null }).pending_approval;
+        const pending = agentState.pending_approval;
         if (!pending) {
+          console.log('[Letta API] No pending approvals on agent');
           return [];
         }
-        const toolCalls = pending.tool_calls || (pending.tool_call ? [pending.tool_call] : []);
+        console.log(`[Letta API] Found pending approval: ${pending.id}, run_id=${pending.run_id}`);
+        
+        // Extract tool calls - handle both Array<ToolCall> and ToolCallDelta formats
+        const rawToolCalls = pending.tool_calls;
+        const toolCallsList: Array<{ tool_call_id: string; name: string }> = [];
+        
+        if (Array.isArray(rawToolCalls)) {
+          for (const tc of rawToolCalls) {
+            if (tc && 'tool_call_id' in tc && tc.tool_call_id) {
+              toolCallsList.push({ tool_call_id: tc.tool_call_id, name: tc.name || 'unknown' });
+            }
+          }
+        } else if (rawToolCalls && typeof rawToolCalls === 'object' && 'tool_call_id' in rawToolCalls && rawToolCalls.tool_call_id) {
+          // ToolCallDelta case
+          toolCallsList.push({ tool_call_id: rawToolCalls.tool_call_id, name: rawToolCalls.name || 'unknown' });
+        }
+        
+        // Fallback to deprecated singular tool_call field
+        if (toolCallsList.length === 0 && pending.tool_call) {
+          const tc = pending.tool_call;
+          if ('tool_call_id' in tc && tc.tool_call_id) {
+            toolCallsList.push({ tool_call_id: tc.tool_call_id, name: tc.name || 'unknown' });
+          }
+        }
+        
         const seen = new Set<string>();
         const approvals: PendingApproval[] = [];
-        for (const tc of toolCalls) {
-          if (!tc?.tool_call_id || seen.has(tc.tool_call_id)) {
-            continue;
-          }
+        for (const tc of toolCallsList) {
+          if (seen.has(tc.tool_call_id)) continue;
           seen.add(tc.tool_call_id);
           approvals.push({
             runId: pending.run_id || 'unknown',
@@ -257,6 +283,7 @@ export async function getPendingApprovals(
             messageId: pending.id,
           });
         }
+        console.log(`[Letta API] Extracted ${approvals.length} pending approval(s): ${approvals.map(a => a.toolName).join(', ')}`);
         return approvals;
       }
     } catch (e) {
@@ -460,6 +487,24 @@ export async function getAgentTools(agentId: string): Promise<Array<{
   }
 }
 
+/**
+ * Ensure no tools on the agent require approval.
+ * Call on startup to proactively prevent stuck approval states.
+ */
+export async function ensureNoToolApprovals(agentId: string): Promise<void> {
+  try {
+    const tools = await getAgentTools(agentId);
+    const approvalTools = tools.filter(t => t.requiresApproval);
+    if (approvalTools.length > 0) {
+      console.log(`[Letta API] Found ${approvalTools.length} tool(s) requiring approval: ${approvalTools.map(t => t.name).join(', ')}`);
+      console.log('[Letta API] Disabling tool approvals for headless operation...');
+      await disableAllToolApprovals(agentId);
+    }
+  } catch (e) {
+    console.warn('[Letta API] Failed to check/disable tool approvals:', e);
+  }
+}
+
 /**
  * Disable approval requirement for ALL tools on an agent.
  * Useful for ensuring a headless deployment doesn't get stuck.