diff --git a/.env.example b/.env.example
index 687281a..430dc0d 100644
--- a/.env.example
+++ b/.env.example
@@ -19,7 +19,7 @@ OPENAI_API_KEY=your-openai-api-key
 PARSER_MODEL=gpt-4.1-mini
 PURCHASE_PARSER_MODEL=gpt-5-mini
 ASSISTANT_MODEL=gpt-5-mini
-ASSISTANT_TIMEOUT_MS=15000
+ASSISTANT_TIMEOUT_MS=20000
 ASSISTANT_MEMORY_MAX_TURNS=12
 ASSISTANT_RATE_LIMIT_BURST=5
 ASSISTANT_RATE_LIMIT_BURST_WINDOW_MS=60000
diff --git a/apps/bot/src/config.ts b/apps/bot/src/config.ts
index 0f7dc03..eb2c51a 100644
--- a/apps/bot/src/config.ts
+++ b/apps/bot/src/config.ts
@@ -133,7 +133,7 @@ export function getBotRuntimeConfig(env: NodeJS.ProcessEnv = process.env): BotRu
     assistantModel: env.ASSISTANT_MODEL?.trim() || 'gpt-5-mini',
     assistantTimeoutMs: parsePositiveInteger(
       env.ASSISTANT_TIMEOUT_MS,
-      15_000,
+      20_000,
       'ASSISTANT_TIMEOUT_MS'
     ),
     assistantMemoryMaxTurns: parsePositiveInteger(
diff --git a/apps/bot/src/dm-assistant.ts b/apps/bot/src/dm-assistant.ts
index d367787..e9223dd 100644
--- a/apps/bot/src/dm-assistant.ts
+++ b/apps/bot/src/dm-assistant.ts
@@ -73,6 +73,26 @@ interface PaymentProposalPayload {
   currency: 'GEL' | 'USD'
 }
 
+function describeError(error: unknown): {
+  errorMessage?: string
+  errorName?: string
+} {
+  if (error instanceof Error) {
+    return {
+      errorMessage: error.message,
+      errorName: error.name
+    }
+  }
+
+  if (typeof error === 'string') {
+    return {
+      errorMessage: error
+    }
+  }
+
+  return {}
+}
+
 function isPrivateChat(ctx: Context): boolean {
   return ctx.chat?.type === 'private'
 }
@@ -749,8 +769,13 @@ export function registerDmAssistant(options: {
       const memory = options.memoryStore.get(telegramUserId)
       const typingIndicator = startTypingIndicator(ctx)
       let pendingReply: PendingAssistantReply | null = null
+      const assistantStartedAt = Date.now()
+      let stage: 'household_context' | 'assistant_response' = 'household_context'
+      let contextBuildMs: number | null = null
+      let assistantResponseMs: number | null = null
 
       try {
+        const contextStartedAt = Date.now()
         const householdContext = await buildHouseholdContext({
           householdId: member.householdId,
           memberId: member.id,
@@ -759,7 +784,10 @@ export function registerDmAssistant(options: {
           householdConfigurationRepository: options.householdConfigurationRepository,
           financeService
         })
+        contextBuildMs = Date.now() - contextStartedAt
         pendingReply = await sendAssistantProcessingReply(ctx, t.processing)
+        stage = 'assistant_response'
+        const assistantResponseStartedAt = Date.now()
         const reply = await options.assistant.respond({
           locale,
           householdContext,
@@ -767,6 +795,7 @@ export function registerDmAssistant(options: {
           recentTurns: memory.turns,
           userMessage: ctx.msg.text
         })
+        assistantResponseMs = Date.now() - assistantResponseStartedAt
 
         options.usageTracker.record({
           householdId: member.householdId,
@@ -788,6 +817,12 @@ export function registerDmAssistant(options: {
             event: 'assistant.reply',
             householdId: member.householdId,
             telegramUserId,
+            contextBuildMs,
+            assistantResponseMs,
+            totalDurationMs: Date.now() - assistantStartedAt,
+            householdContextChars: householdContext.length,
+            recentTurnsCount: memory.turns.length,
+            memorySummaryChars: memory.summary?.length ?? 0,
             inputTokens: reply.usage.inputTokens,
             outputTokens: reply.usage.outputTokens,
             totalTokens: reply.usage.totalTokens
@@ -802,6 +837,11 @@ export function registerDmAssistant(options: {
             event: 'assistant.reply_failed',
             householdId: member.householdId,
             telegramUserId,
+            stage,
+            contextBuildMs,
+            assistantResponseMs,
+            totalDurationMs: Date.now() - assistantStartedAt,
+            ...describeError(error),
             error
           },
           'DM assistant reply failed'
diff --git a/infra/terraform/terraform.tfvars.example b/infra/terraform/terraform.tfvars.example
index 645f7e4..83246f0 100644
--- a/infra/terraform/terraform.tfvars.example
+++ b/infra/terraform/terraform.tfvars.example
@@ -14,7 +14,7 @@ openai_api_key_secret_id = "openai-api-key"
 bot_parser_model             = "gpt-4.1-mini"
 bot_purchase_parser_model    = "gpt-5-mini"
 bot_assistant_model          = "gpt-5-mini"
-bot_assistant_timeout_ms     = 15000
+bot_assistant_timeout_ms     = 20000
 bot_assistant_memory_max_turns = 12
 bot_assistant_rate_limit_burst = 5
 bot_assistant_rate_limit_burst_window_ms = 60000
diff --git a/packages/config/src/env.ts b/packages/config/src/env.ts
index 1cc4631..e2a2ecb 100644
--- a/packages/config/src/env.ts
+++ b/packages/config/src/env.ts
@@ -34,7 +34,7 @@ const server = {
   PARSER_MODEL: z.string().min(1).default('gpt-4.1-mini'),
   PURCHASE_PARSER_MODEL: z.string().min(1).default('gpt-5-mini'),
   ASSISTANT_MODEL: z.string().min(1).default('gpt-5-mini'),
-  ASSISTANT_TIMEOUT_MS: z.coerce.number().int().positive().default(15000),
+  ASSISTANT_TIMEOUT_MS: z.coerce.number().int().positive().default(20000),
   ASSISTANT_MEMORY_MAX_TURNS: z.coerce.number().int().positive().default(12),
   ASSISTANT_RATE_LIMIT_BURST: z.coerce.number().int().positive().default(5),
   ASSISTANT_RATE_LIMIT_BURST_WINDOW_MS: z.coerce.number().int().positive().default(60000),