diff --git a/src/commands/enrich.ts b/src/commands/enrich.ts
index 99a04ed24..da59c59d6 100644
--- a/src/commands/enrich.ts
+++ b/src/commands/enrich.ts
@@ -33,7 +33,7 @@ import type { BrainEngine } from '../core/engine.ts';
 import type { EnrichCandidate, PageType } from '../core/types.ts';
 import { operations } from '../core/operations.ts';
 import type { OperationContext } from '../core/operations.ts';
-import { isAvailable, chat, getChatModel, withBudgetTracker } from '../core/ai/gateway.ts';
+import { configureGatewayIfUninitialized, isAvailable, chat, getChatModel, withBudgetTracker } from '../core/ai/gateway.ts';
 import { BudgetTracker, BudgetExhausted } from '../core/budget/budget-tracker.ts';
 import { hybridSearch } from '../core/search/hybrid.ts';
 import { serializeMarkdown } from '../core/markdown.ts';
@@ -807,7 +807,9 @@ export async function runEnrich(engine: BrainEngine, args: string[]): Promise<vo
     process.exit(1);
   }
 
-  // Chat gateway required for non-dry-run.
+  // Chat gateway is required for non-dry-run. Recover a cold singleton before
+  // reporting an availability error (#2590).
+  if (!parsed.dryRun && !isAvailable('chat')) configureGatewayIfUninitialized();
   if (!parsed.dryRun && !isAvailable('chat')) {
     console.error('Chat gateway unavailable. Configure a chat model (e.g. `gbrain config set chat_model anthropic:claude-haiku-4-5`), or pass --dry-run to preview candidates.');
     process.exit(1);
diff --git a/src/commands/extract-conversation-facts.ts b/src/commands/extract-conversation-facts.ts
index 65e8a4ac4..693902230 100644
--- a/src/commands/extract-conversation-facts.ts
+++ b/src/commands/extract-conversation-facts.ts
@@ -71,7 +71,7 @@ import {
   extractFactsFromTurn,
   isFactsExtractionEnabled,
 } from '../core/facts/extract.ts';
-import { isAvailable, withBudgetTracker } from '../core/ai/gateway.ts';
+import { configureGatewayIfUninitialized, isAvailable, withBudgetTracker } from '../core/ai/gateway.ts';
 import { BudgetTracker, BudgetExhausted } from '../core/budget/budget-tracker.ts';
 import { listSources } from '../core/sources-ops.ts';
 import {
@@ -81,7 +81,6 @@ import {
 } from '../core/op-checkpoint.ts';
 import { createProgress } from '../core/progress.ts';
 import { getCliOptions, cliOptsToProgressOptions, maybeBackground } from '../core/cli-options.ts';
-import { loadConfig } from '../core/config.ts';
 import { createHash } from 'crypto';
 // v0.41.15.0 (T5): worker-pool primitive + per-source-clamp wrapper +
 // per-page advisory lock + delete-orphans-first replay safety. See plan
@@ -1354,7 +1353,9 @@ export async function runExtractConversationFacts(
     process.exit(1);
   }
 
-  // Chat gateway is required for non-dry-run.
+  // Chat gateway is required for non-dry-run. Recover a cold singleton before
+  // reporting an availability error (#2590).
+  if (!parsed.dryRun && !isAvailable('chat')) configureGatewayIfUninitialized();
   if (!parsed.dryRun && !isAvailable('chat')) {
     console.error('Chat gateway unavailable. Configure an Anthropic or compatible chat model, or pass --dry-run to preview segmentation.');
     process.exit(1);
diff --git a/src/core/ai/gateway.ts b/src/core/ai/gateway.ts
index a55dcc51c..08ee43cea 100644
--- a/src/core/ai/gateway.ts
+++ b/src/core/ai/gateway.ts
@@ -53,6 +53,8 @@ import { dimsProviderOptions } from './dims.ts';
 import { hasAnthropicKey } from './anthropic-key.ts';
 import { AIConfigError, AITransientError, normalizeAIError } from './errors.ts';
 import { runGuardrails, hasGuardrails, type GuardrailHook } from '../guardrails.ts';
+import { loadConfig } from '../config.ts';
+import { buildGatewayConfig } from './build-gateway-config.ts';
 
 // ---- Gateway-wide AI-HTTP timeout (v0.42.20.0, #1762/#1775) ----
 //
@@ -117,6 +119,18 @@ const DEFAULT_RERANKER_MODEL = 'zeroentropyai:zerank-2';
 let _config: AIGatewayConfig | null = null;
 const _modelCache = new Map<string, any>();
 
+/**
+ * Recover the process-global gateway for foreground command entrypoints that
+ * were reached without cli.ts's normal engine-connect initialization (#2590).
+ * Existing configured gateways, including their DB-resolved model overrides,
+ * are deliberately left unchanged.
+ */
+export function configureGatewayIfUninitialized(): void {
+  if (_config) return;
+  const config = loadConfig();
+  if (config) configureGateway(buildGatewayConfig(config));
+}
+
 /**
  * v0.31.12 recipe-models merge: per-gateway-instance set of model ids the
  * user opted into via config. Keyed by provider id (`anthropic`, `openai`,
diff --git a/test/foreground-chat-gateway-init.serial.test.ts b/test/foreground-chat-gateway-init.serial.test.ts
new file mode 100644
index 000000000..5bdc7879d
--- /dev/null
+++ b/test/foreground-chat-gateway-init.serial.test.ts
@@ -0,0 +1,77 @@
+/**
+ * Foreground batch commands are normally reached after cli.ts configures the
+ * process-global gateway. Keep the command boundary defensive as well: an
+ * embedding/CLI loader can leave that singleton cold while the persisted chat
+ * configuration and provider credentials are valid (#2590).
+ */
+
+import { afterEach, beforeEach, describe, expect, spyOn, test } from 'bun:test';
+import { mkdirSync, mkdtempSync, rmSync, writeFileSync } from 'node:fs';
+import { tmpdir } from 'node:os';
+import { join } from 'node:path';
+import { isAvailable, resetGateway } from '../src/core/ai/gateway.ts';
+import { runExtractConversationFacts } from '../src/commands/extract-conversation-facts.ts';
+import { runEnrich } from '../src/commands/enrich.ts';
+
+let home: string;
+const originalHome = process.env.GBRAIN_HOME;
+const originalOpenAiKey = process.env.OPENAI_API_KEY;
+
+beforeEach(() => {
+  home = mkdtempSync(join(tmpdir(), 'gbrain-foreground-gateway-'));
+  mkdirSync(join(home, '.gbrain'));
+  writeFileSync(join(home, '.gbrain', 'config.json'), JSON.stringify({
+    engine: 'pglite',
+    database_path: join(home, '.gbrain', 'brain.pglite'),
+    chat_model: 'openai:example-chat-model',
+  }));
+  process.env.GBRAIN_HOME = home;
+  process.env.OPENAI_API_KEY = 'test-key';
+  resetGateway();
+});
+
+afterEach(() => {
+  resetGateway();
+  if (originalHome === undefined) delete process.env.GBRAIN_HOME;
+  else process.env.GBRAIN_HOME = originalHome;
+  if (originalOpenAiKey === undefined) delete process.env.OPENAI_API_KEY;
+  else process.env.OPENAI_API_KEY = originalOpenAiKey;
+  rmSync(home, { recursive: true, force: true });
+});
+
+describe('foreground chat gateway initialization (#2590)', () => {
+  test('extract-conversation-facts initializes a cold gateway from persisted config before its availability gate', async () => {
+    const exit = spyOn(process, 'exit').mockImplementation((() => {
+      throw new Error('unexpected process.exit');
+    }) as never);
+
+    try {
+      await runExtractConversationFacts({
+        executeRaw: async () => [],
+      } as never, []);
+    } finally {
+      exit.mockRestore();
+    }
+
+    expect(exit).not.toHaveBeenCalled();
+    expect(isAvailable('chat')).toBe(true);
+  });
+
+  test('enrich initializes a cold gateway from persisted config before its availability gate', async () => {
+    const exit = spyOn(process, 'exit').mockImplementation((() => {
+      throw new Error('unexpected process.exit');
+    }) as never);
+
+    try {
+      await runEnrich({
+        executeRaw: async () => [],
+        getConfig: async () => null,
+      } as never, ['--yes']);
+    } finally {
+      exit.mockRestore();
+    }
+
+    expect(exit).not.toHaveBeenCalled();
+    expect(isAvailable('chat')).toBe(true);
+  });
+});