diff --git a/package.json b/package.json
index 54b70a1..c69b273 100644
--- a/package.json
+++ b/package.json
@@ -23,6 +23,7 @@
     "test": "vitest",
     "test:run": "vitest run --exclude 'e2e/**'",
     "lint:console": "bash scripts/no-console.sh",
+    "repro:context-window-reset": "tsx scripts/repro-context-window-reset.ts",
     "test:e2e": "vitest run e2e/",
     "skills": "tsx src/cli.ts skills",
     "skills:list": "tsx src/cli.ts skills list",
diff --git a/scripts/repro-context-window-reset.ts b/scripts/repro-context-window-reset.ts
new file mode 100644
index 0000000..7e0cdfb
--- /dev/null
+++ b/scripts/repro-context-window-reset.ts
@@ -0,0 +1,313 @@
+#!/usr/bin/env tsx
+
+import { createHash } from 'node:crypto';
+
+import { Letta } from '@letta-ai/letta-client';
+import { createAgent, resumeSession } from '@letta-ai/letta-code-sdk';
+
+type ParsedArgs = {
+  agentId?: string;
+  model?: string;
+  targetWindow: number;
+  iterations: number;
+  preSessionIdleMs: number;
+  keepAgent: boolean;
+  skipControl: boolean;
+  baseUrl?: string;
+  apiKey?: string;
+  includeDirectSystemPatch: boolean;
+};
+
+type AgentSnapshot = {
+  at: string;
+  contextWindowLimit: number | null;
+  llmContextWindow: number | null;
+  effectiveContextWindow: number | null;
+  systemHash: string;
+  systemLength: number;
+  compactionSettings: unknown;
+};
+
+type StepResult = {
+  step: string;
+  snapshot: AgentSnapshot;
+  changedFromTarget: boolean;
+};
+
+function printUsage(): void {
+  console.log(`
+Repro: context_window_limit drift after SDK memfs toggle updates.
+
+Usage:
+  npm run repro:context-window-reset -- [options]
+
+Options:
+  --agent-id <id>              Use an existing agent instead of creating one.
+  --model <handle>             Model handle for created agent.
+  --target-window <number>     Context window limit to pin before triggers (default: 38000).
+  --iterations <number>        Number of memfs-false init cycles (default: 3).
+  --pre-idle-ms <number>       Idle wait after pin and before SDK steps (default: 2000).
+  --keep-agent                 Keep auto-created agent (default: delete it).
+  --skip-control               Skip control init with memfs omitted.
+  --direct-system-patch        Also run direct {system:<same>} patch via API client.
+  --base-url <url>             Override LETTA_BASE_URL.
+  --api-key <key>              Override LETTA_API_KEY.
+  --help                       Show this message.
+
+Required env (unless passed via flags):
+  LETTA_API_KEY
+Optional env:
+  LETTA_BASE_URL (default: https://api.letta.com)
+`);
+}
+
+function parseArgs(argv: string[]): ParsedArgs {
+  const out: ParsedArgs = {
+    targetWindow: 38000,
+    iterations: 3,
+    preSessionIdleMs: 2000,
+    keepAgent: false,
+    skipControl: false,
+    includeDirectSystemPatch: false,
+  };
+
+  for (let i = 0; i < argv.length; i += 1) {
+    const arg = argv[i];
+    if (arg === '--help' || arg === '-h') {
+      printUsage();
+      process.exit(0);
+    }
+    if (arg === '--agent-id') {
+      out.agentId = argv[++i];
+      continue;
+    }
+    if (arg === '--model') {
+      out.model = argv[++i];
+      continue;
+    }
+    if (arg === '--target-window') {
+      out.targetWindow = Number(argv[++i]);
+      continue;
+    }
+    if (arg === '--iterations') {
+      out.iterations = Number(argv[++i]);
+      continue;
+    }
+    if (arg === '--pre-idle-ms') {
+      out.preSessionIdleMs = Number(argv[++i]);
+      continue;
+    }
+    if (arg === '--keep-agent') {
+      out.keepAgent = true;
+      continue;
+    }
+    if (arg === '--skip-control') {
+      out.skipControl = true;
+      continue;
+    }
+    if (arg === '--direct-system-patch') {
+      out.includeDirectSystemPatch = true;
+      continue;
+    }
+    if (arg === '--base-url') {
+      out.baseUrl = argv[++i];
+      continue;
+    }
+    if (arg === '--api-key') {
+      out.apiKey = argv[++i];
+      continue;
+    }
+    throw new Error(`Unknown argument: ${arg}`);
+  }
+
+  if (!Number.isFinite(out.targetWindow) || out.targetWindow <= 0) {
+    throw new Error(`--target-window must be a positive number, got: ${out.targetWindow}`);
+  }
+  if (!Number.isFinite(out.iterations) || out.iterations <= 0) {
+    throw new Error(`--iterations must be a positive number, got: ${out.iterations}`);
+  }
+  if (!Number.isFinite(out.preSessionIdleMs) || out.preSessionIdleMs < 0) {
+    throw new Error(`--pre-idle-ms must be >= 0, got: ${out.preSessionIdleMs}`);
+  }
+
+  return out;
+}
+
+function hashText(value: string): string {
+  return createHash('sha256').update(value).digest('hex').slice(0, 12);
+}
+
+function sleep(ms: number): Promise<void> {
+  return new Promise((resolve) => setTimeout(resolve, ms));
+}
+
+async function getSnapshot(client: Letta, agentId: string): Promise<AgentSnapshot> {
+  const state = await client.agents.retrieve(agentId);
+  const unsafe = state as Record<string, unknown>;
+  const contextWindowLimit = typeof unsafe.context_window_limit === 'number'
+    ? unsafe.context_window_limit
+    : null;
+  const llmConfig = unsafe.llm_config as Record<string, unknown> | undefined;
+  const llmContextWindow = llmConfig && typeof llmConfig.context_window === 'number'
+    ? llmConfig.context_window
+    : null;
+  const effectiveContextWindow = contextWindowLimit ?? llmContextWindow;
+  const system = typeof unsafe.system === 'string' ? unsafe.system : '';
+  const compactionSettings = unsafe.compaction_settings ?? null;
+
+  return {
+    at: new Date().toISOString(),
+    contextWindowLimit,
+    llmContextWindow,
+    effectiveContextWindow,
+    systemHash: hashText(system),
+    systemLength: system.length,
+    compactionSettings,
+  };
+}
+
+function isWindowChanged(snapshot: AgentSnapshot, targetWindow: number): boolean {
+  return snapshot.effectiveContextWindow !== targetWindow;
+}
+
+async function initializeAndClose(agentId: string, memfs: boolean | undefined): Promise<void> {
+  const opts = memfs === undefined ? {} : { memfs };
+  const session = resumeSession(agentId, opts);
+  try {
+    await session.initialize();
+  } finally {
+    session.close();
+  }
+}
+
+async function main(): Promise<void> {
+  const args = parseArgs(process.argv.slice(2));
+  const baseURL = args.baseUrl || process.env.LETTA_BASE_URL || 'https://api.letta.com';
+  const apiKey = args.apiKey || process.env.LETTA_API_KEY;
+
+  if (!apiKey) {
+    throw new Error('LETTA_API_KEY is required (set env or pass --api-key).');
+  }
+
+  process.env.LETTA_BASE_URL = baseURL;
+  process.env.LETTA_API_KEY = apiKey;
+
+  const client = new Letta({ apiKey, baseURL });
+  const startedAt = new Date().toISOString();
+
+  let agentId = args.agentId;
+  let createdAgent = false;
+
+  if (!agentId) {
+    agentId = await createAgent({
+      ...(args.model ? { model: args.model } : {}),
+      // Keep baseline deterministic: avoid cloud auto-memfs behavior on new agents.
+      memfs: false,
+      tags: ['origin:context-window-repro'],
+    });
+    createdAgent = true;
+  }
+
+  console.log(`Using agent: ${agentId}${createdAgent ? ' (created for repro)' : ''}`);
+
+  const initial = await getSnapshot(client, agentId);
+
+  await client.agents.update(agentId, { context_window_limit: args.targetWindow });
+  await sleep(750);
+  const afterPin = await getSnapshot(client, agentId);
+
+  const steps: StepResult[] = [];
+
+  if (args.preSessionIdleMs > 0) {
+    await sleep(args.preSessionIdleMs);
+    const idle = await getSnapshot(client, agentId);
+    steps.push({
+      step: `control: idle wait ${args.preSessionIdleMs}ms (no SDK session)`,
+      snapshot: idle,
+      changedFromTarget: isWindowChanged(idle, args.targetWindow),
+    });
+  }
+
+  if (!args.skipControl) {
+    await initializeAndClose(agentId, undefined);
+    await sleep(750);
+    const control = await getSnapshot(client, agentId);
+    steps.push({
+      step: 'control: sdk init with memfs omitted',
+      snapshot: control,
+      changedFromTarget: isWindowChanged(control, args.targetWindow),
+    });
+  }
+
+  for (let i = 1; i <= args.iterations; i += 1) {
+    await initializeAndClose(agentId, false);
+    await sleep(750);
+    const snap = await getSnapshot(client, agentId);
+    steps.push({
+      step: `trigger ${i}: sdk init with memfs=false (--no-memfs)`,
+      snapshot: snap,
+      changedFromTarget: isWindowChanged(snap, args.targetWindow),
+    });
+  }
+
+  if (args.includeDirectSystemPatch) {
+    const latest = await getSnapshot(client, agentId);
+    const state = await client.agents.retrieve(agentId);
+    const system = typeof (state as Record<string, unknown>).system === 'string'
+      ? (state as Record<string, unknown>).system as string
+      : '';
+    await client.agents.update(agentId, { system });
+    await sleep(750);
+    const afterDirectPatch = await getSnapshot(client, agentId);
+    steps.push({
+      step: 'trigger: direct client.agents.update({system: sameText})',
+      snapshot: afterDirectPatch,
+      changedFromTarget: isWindowChanged(afterDirectPatch, args.targetWindow),
+    });
+
+    if (latest.systemHash !== afterDirectPatch.systemHash) {
+      console.warn('Note: system hash changed across direct system patch step.');
+    }
+  }
+
+  const reproduced = steps.some((s) => s.changedFromTarget);
+  const finishedAt = new Date().toISOString();
+
+  const report = {
+    scenario: 'context-window-limit drift on partial agent updates',
+    startedAt,
+    finishedAt,
+    baseURL,
+    agentId,
+    createdAgent,
+    targetWindow: args.targetWindow,
+    initial,
+    afterPin,
+    steps,
+    note: 'effectiveContextWindow uses context_window_limit when available, otherwise llm_config.context_window.',
+    reproduced,
+    summary: reproduced
+      ? 'BUG REPRODUCED: context_window_limit changed away from pinned value.'
+      : 'No drift observed in this run.',
+  };
+
+  console.log('\n=== Repro Report (JSON) ===');
+  console.log(JSON.stringify(report, null, 2));
+
+  if (createdAgent && !args.keepAgent) {
+    await client.agents.delete(agentId);
+    console.log(`Deleted temporary agent: ${agentId}`);
+  } else if (createdAgent && args.keepAgent) {
+    console.log(`Kept temporary agent for inspection: ${agentId}`);
+  }
+
+  if (reproduced) {
+    process.exitCode = 2;
+  }
+}
+
+main().catch((error) => {
+  const message = error instanceof Error ? error.stack || error.message : String(error);
+  console.error(message);
+  process.exit(1);
+});
diff --git a/src/config/memfs.test.ts b/src/config/memfs.test.ts
new file mode 100644
index 0000000..ea0c9aa
--- /dev/null
+++ b/src/config/memfs.test.ts
@@ -0,0 +1,58 @@
+import { describe, expect, it } from 'vitest';
+
+import { resolveSessionMemfs } from './memfs.js';
+
+describe('resolveSessionMemfs', () => {
+  it('uses explicit agent config first', () => {
+    const result = resolveSessionMemfs({
+      configuredMemfs: true,
+      envMemfs: 'false',
+      serverMode: 'api',
+    });
+
+    expect(result).toEqual({ value: true, source: 'config' });
+  });
+
+  it('uses LETTABOT_MEMFS env override when config is unset', () => {
+    const result = resolveSessionMemfs({
+      envMemfs: 'false',
+      serverMode: 'api',
+    });
+
+    expect(result).toEqual({ value: false, source: 'env' });
+  });
+
+  it('defaults to memfs false in docker/selfhosted mode when unset', () => {
+    const result = resolveSessionMemfs({
+      serverMode: 'selfhosted',
+    });
+
+    expect(result).toEqual({ value: false, source: 'default-docker' });
+  });
+
+  it('leaves memfs unchanged in api/cloud mode when unset', () => {
+    const result = resolveSessionMemfs({
+      serverMode: 'cloud',
+    });
+
+    expect(result).toEqual({ value: undefined, source: 'unset' });
+  });
+
+  it('ignores invalid LETTABOT_MEMFS values', () => {
+    const result = resolveSessionMemfs({
+      envMemfs: 'yes',
+      serverMode: 'api',
+    });
+
+    expect(result).toEqual({ value: undefined, source: 'unset' });
+  });
+
+  it('treats null configured memfs as unset and applies docker default', () => {
+    const result = resolveSessionMemfs({
+      configuredMemfs: null as unknown as boolean,
+      serverMode: 'selfhosted',
+    });
+
+    expect(result).toEqual({ value: false, source: 'default-docker' });
+  });
+});
diff --git a/src/config/memfs.ts b/src/config/memfs.ts
new file mode 100644
index 0000000..69ff82d
--- /dev/null
+++ b/src/config/memfs.ts
@@ -0,0 +1,48 @@
+import { isDockerServerMode, type ServerMode } from './types.js';
+
+export type ResolvedMemfsSource = 'config' | 'env' | 'default-docker' | 'unset';
+
+export interface ResolveSessionMemfsInput {
+  configuredMemfs?: boolean;
+  envMemfs?: string;
+  serverMode?: ServerMode;
+}
+
+export interface ResolveSessionMemfsResult {
+  value: boolean | undefined;
+  source: ResolvedMemfsSource;
+}
+
+function parseBooleanEnv(value?: string): boolean | undefined {
+  if (value === 'true') return true;
+  if (value === 'false') return false;
+  return undefined;
+}
+
+/**
+ * Resolve the memfs value forwarded to SDK session options.
+ *
+ * Precedence:
+ * 1) Per-agent config (`features.memfs`)
+ * 2) `LETTABOT_MEMFS` env var (`true`/`false`)
+ * 3) Default `false` in docker/self-hosted mode (safety)
+ * 4) `undefined` in API mode (leave agent memfs unchanged)
+ */
+export function resolveSessionMemfs(input: ResolveSessionMemfsInput): ResolveSessionMemfsResult {
+  // Runtime config parsing can surface non-boolean values (e.g. YAML `memfs:` -> null).
+  // Only treat explicit booleans as configured; everything else falls through.
+  if (typeof input.configuredMemfs === 'boolean') {
+    return { value: input.configuredMemfs, source: 'config' };
+  }
+
+  const envMemfs = parseBooleanEnv(input.envMemfs);
+  if (envMemfs !== undefined) {
+    return { value: envMemfs, source: 'env' };
+  }
+
+  if (isDockerServerMode(input.serverMode)) {
+    return { value: false, source: 'default-docker' };
+  }
+
+  return { value: undefined, source: 'unset' };
+}
diff --git a/src/core/session-manager.ts b/src/core/session-manager.ts
index 4c73883..70a3792 100644
--- a/src/core/session-manager.ts
+++ b/src/core/session-manager.ts
@@ -20,6 +20,23 @@ import { createLogger } from '../logger.js';
 
 const log = createLogger('Session');
 
+function formatMemfsStartupOption(memfs: boolean | undefined): string {
+  if (memfs === true) return 'enabled (--memfs)';
+  if (memfs === false) return 'disabled (--no-memfs)';
+  return 'unchanged (omitted)';
+}
+
+function formatSleeptimeStartupOption(
+  sleeptime: BotConfig['sleeptime'],
+): string {
+  if (!sleeptime) return 'none';
+  const parts: string[] = [];
+  if (sleeptime.trigger) parts.push(`trigger=${sleeptime.trigger}`);
+  if (sleeptime.behavior) parts.push(`behavior=${sleeptime.behavior}`);
+  if (sleeptime.stepCount !== undefined) parts.push(`stepCount=${sleeptime.stepCount}`);
+  return parts.length > 0 ? parts.join(', ') : 'configured';
+}
+
 function toConcreteConversationId(value: string | null | undefined): string | null {
   if (!value) return null;
   const trimmed = value.trim();
@@ -313,6 +330,11 @@ export class SessionManager {
     }
 
     // Initialize eagerly so the subprocess is ready before the first send()
+    log.info(
+      `Session startup options (key=${key}): ` +
+      `memfs=${formatMemfsStartupOption(this.config.memfs)}, ` +
+      `sleeptime=${formatSleeptimeStartupOption(this.config.sleeptime)}`,
+    );
     log.info(`Initializing session subprocess (key=${key})...`);
     try {
       await this.withSessionTimeout(session.initialize(), `Session initialize (key=${key})`);
diff --git a/src/main.ts b/src/main.ts
index a897ac3..398ec4a 100644
--- a/src/main.ts
+++ b/src/main.ts
@@ -24,6 +24,7 @@ import {
   serverModeLabel,
   wasLoadedFromFleetConfig,
 } from './config/index.js';
+import { resolveSessionMemfs } from './config/memfs.js';
 import { getCronDataDir, getDataDir, getWorkingDir, hasRailwayVolume, resolveWorkingDirPath } from './utils/paths.js';
 import { parseCsvList, parseNonNegativeNumber } from './utils/parse.js';
 import { createLogger, setLogLevel } from './logger.js';
@@ -299,21 +300,23 @@ async function main() {
   for (const agentConfig of agents) {
     log.info(`Configuring agent: ${agentConfig.name}`);
     
-    // Resolve memfs: YAML config takes precedence, then env var, then default false.
-    // Default false prevents the SDK from auto-enabling memfs, which crashes on
-    // self-hosted Letta servers that don't have the git endpoint.
-    const resolvedMemfs = agentConfig.features?.memfs ?? (process.env.LETTABOT_MEMFS === 'true' ? true : false);
+    const resolvedMemfsResult = resolveSessionMemfs({
+      configuredMemfs: agentConfig.features?.memfs,
+      envMemfs: process.env.LETTABOT_MEMFS,
+      serverMode: yamlConfig.server.mode,
+    });
+    const resolvedMemfs = resolvedMemfsResult.value;
     const configuredSleeptime = agentConfig.features?.sleeptime;
     // Treat missing trigger as active (conservative): only `trigger: 'off'` explicitly disables.
     const sleeptimeRequiresMemfs = !!configuredSleeptime && configuredSleeptime.trigger !== 'off';
-    const effectiveSleeptime = !resolvedMemfs && sleeptimeRequiresMemfs
+    const effectiveSleeptime = resolvedMemfs === false && sleeptimeRequiresMemfs
       ? undefined
       : configuredSleeptime;
 
-    if (!resolvedMemfs && sleeptimeRequiresMemfs) {
+    if (resolvedMemfs === false && sleeptimeRequiresMemfs) {
       log.warn(
         `Agent ${agentConfig.name}: sleeptime is configured but memfs is disabled; ` +
-        `sleeptime will be ignored. Enable features.memfs (or LETTABOT_MEMFS=true) to use sleeptime.`
+        `sleeptime will be ignored. Enable features.memfs (or set LETTABOT_MEMFS=true) to use sleeptime.`
       );
     }
 
@@ -359,8 +362,14 @@ async function main() {
     
     // Log memfs config (from either YAML or env var)
     if (resolvedMemfs !== undefined) {
-      const source = agentConfig.features?.memfs !== undefined ? '' : ' (from LETTABOT_MEMFS env)';
+      const source = resolvedMemfsResult.source === 'config'
+        ? ''
+        : resolvedMemfsResult.source === 'env'
+          ? ' (from LETTABOT_MEMFS env)'
+          : ' (default for docker/selfhosted mode)';
       log.info(`Agent ${agentConfig.name}: memfs ${resolvedMemfs ? 'enabled' : 'disabled'}${source}`);
+    } else {
+      log.info(`Agent ${agentConfig.name}: memfs unchanged (not explicitly configured)`);
     }
 
     // Apply explicit agent ID from config (before store verification)