diff --git a/src/agents/auth-profiles/oauth.ts b/src/agents/auth-profiles/oauth.ts
index 8cf05f5871..60c8a731b1 100644
--- a/src/agents/auth-profiles/oauth.ts
+++ b/src/agents/auth-profiles/oauth.ts
@@ -18,7 +18,7 @@ import { ensureAuthProfileStore, saveAuthProfileStore } from "./store.js";
 const OAUTH_PROVIDER_IDS = new Set(getOAuthProviders().map((provider) => provider.id));
 
 const resolveOAuthProvider = (provider: string): OAuthProvider | null =>
-  OAUTH_PROVIDER_IDS.has(provider as OAuthProvider) ? (provider as OAuthProvider) : null;
+  OAUTH_PROVIDER_IDS.has(provider) ? provider : null;
 
 function buildOAuthApiKey(provider: string, credentials: OAuthCredentials): string {
   const needsProjectId = provider === "google-gemini-cli" || provider === "google-antigravity";
diff --git a/src/agents/pi-embedded-runner/compact.ts b/src/agents/pi-embedded-runner/compact.ts
index 0e010e0eea..dc4389d47b 100644
--- a/src/agents/pi-embedded-runner/compact.ts
+++ b/src/agents/pi-embedded-runner/compact.ts
@@ -1,6 +1,7 @@
 import {
   createAgentSession,
   estimateTokens,
+  DefaultResourceLoader,
   SessionManager,
   SettingsManager,
 } from "@mariozechner/pi-coding-agent";
@@ -64,7 +65,11 @@ import { log } from "./logger.js";
 import { buildModelAliasLines, resolveModel } from "./model.js";
 import { buildEmbeddedSandboxInfo } from "./sandbox-info.js";
 import { prewarmSessionFile, trackSessionManagerAccess } from "./session-manager-cache.js";
-import { buildEmbeddedSystemPrompt, createSystemPromptOverride } from "./system-prompt.js";
+import {
+  applySystemPromptOverrideToSession,
+  buildEmbeddedSystemPrompt,
+  createSystemPromptOverride,
+} from "./system-prompt.js";
 import { splitSdkTools } from "./tool-split.js";
 import { describeUnknownError, mapThinkingLevel, resolveExecToolDefaults } from "./utils.js";
 
@@ -347,7 +352,7 @@ export async function compactEmbeddedPiSessionDirect(
       userTimeFormat,
       contextFiles,
     });
-    const systemPrompt = createSystemPromptOverride(appendPrompt);
+    const systemPromptOverride = createSystemPromptOverride(appendPrompt);
 
     const sessionLock = await acquireSessionWriteLock({
       sessionFile: params.sessionFile,
@@ -383,6 +388,13 @@ export async function compactEmbeddedPiSessionDirect(
         sandboxEnabled: !!sandbox?.enabled,
       });
 
+      const resourceLoader = new DefaultResourceLoader({
+        cwd: resolvedWorkspace,
+        agentDir,
+        settingsManager,
+        additionalExtensionPaths,
+      });
+      await resourceLoader.reload();
       const { session } = await createAgentSession({
         cwd: resolvedWorkspace,
         agentDir,
@@ -394,11 +406,9 @@ export async function compactEmbeddedPiSessionDirect(
         customTools,
         sessionManager,
         settingsManager,
-        systemPrompt,
-        additionalExtensionPaths,
-        skills: [],
-        contextFiles: [],
+        resourceLoader,
       });
+      applySystemPromptOverrideToSession(session, systemPromptOverride);
 
       try {
         const prior = await sanitizeSessionHistory({
diff --git a/src/agents/pi-embedded-runner/run/attempt.ts b/src/agents/pi-embedded-runner/run/attempt.ts
index fb4984e45f..cc013b5083 100644
--- a/src/agents/pi-embedded-runner/run/attempt.ts
+++ b/src/agents/pi-embedded-runner/run/attempt.ts
@@ -1,7 +1,12 @@
 import type { AgentMessage } from "@mariozechner/pi-agent-core";
 import type { ImageContent } from "@mariozechner/pi-ai";
 import { streamSimple } from "@mariozechner/pi-ai";
-import { createAgentSession, SessionManager, SettingsManager } from "@mariozechner/pi-coding-agent";
+import {
+  createAgentSession,
+  DefaultResourceLoader,
+  SessionManager,
+  SettingsManager,
+} from "@mariozechner/pi-coding-agent";
 import fs from "node:fs/promises";
 import os from "node:os";
 import type { EmbeddedRunAttemptParams, EmbeddedRunAttemptResult } from "./types.js";
@@ -78,7 +83,11 @@ import {
 import { buildEmbeddedSandboxInfo } from "../sandbox-info.js";
 import { prewarmSessionFile, trackSessionManagerAccess } from "../session-manager-cache.js";
 import { prepareSessionManagerForRun } from "../session-manager-init.js";
-import { buildEmbeddedSystemPrompt, createSystemPromptOverride } from "../system-prompt.js";
+import {
+  applySystemPromptOverrideToSession,
+  buildEmbeddedSystemPrompt,
+  createSystemPromptOverride,
+} from "../system-prompt.js";
 import { splitSdkTools } from "../tool-split.js";
 import { describeUnknownError, mapThinkingLevel } from "../utils.js";
 import { detectAndLoadPromptImages } from "./images.js";
@@ -385,7 +394,8 @@ export async function runEmbeddedAttempt(
       skillsPrompt,
       tools,
     });
-    const systemPrompt = createSystemPromptOverride(appendPrompt);
+    const systemPromptOverride = createSystemPromptOverride(appendPrompt);
+    const systemPromptText = systemPromptOverride();
 
     const sessionLock = await acquireSessionWriteLock({
       sessionFile: params.sessionFile,
@@ -457,6 +467,13 @@ export async function runEmbeddedAttempt(
 
       const allCustomTools = [...customTools, ...clientToolDefs];
 
+      const resourceLoader = new DefaultResourceLoader({
+        cwd: resolvedWorkspace,
+        agentDir,
+        settingsManager,
+        additionalExtensionPaths,
+      });
+      await resourceLoader.reload();
       ({ session } = await createAgentSession({
         cwd: resolvedWorkspace,
         agentDir,
@@ -468,11 +485,9 @@ export async function runEmbeddedAttempt(
         customTools: allCustomTools,
         sessionManager,
         settingsManager,
-        systemPrompt,
-        additionalExtensionPaths,
-        skills: [],
-        contextFiles: [],
+        resourceLoader,
       }));
+      applySystemPromptOverrideToSession(session, systemPromptOverride);
       if (!session) {
         throw new Error("Embedded agent session missing");
       }
@@ -513,7 +528,7 @@ export async function runEmbeddedAttempt(
       if (cacheTrace) {
         cacheTrace.recordStage("session:loaded", {
           messages: activeSession.messages,
-          system: systemPrompt,
+          system: systemPromptText,
           note: "after session create",
         });
         activeSession.agent.streamFn = cacheTrace.wrapStreamFn(activeSession.agent.streamFn);
diff --git a/src/agents/pi-embedded-runner/system-prompt.ts b/src/agents/pi-embedded-runner/system-prompt.ts
index 16ff41db7b..70f85a74a7 100644
--- a/src/agents/pi-embedded-runner/system-prompt.ts
+++ b/src/agents/pi-embedded-runner/system-prompt.ts
@@ -1,4 +1,5 @@
 import type { AgentTool } from "@mariozechner/pi-agent-core";
+import type { AgentSession } from "@mariozechner/pi-coding-agent";
 import type { ResolvedTimeFormat } from "../date-time.js";
 import type { EmbeddedContextFile } from "../pi-embedded-helpers.js";
 import type { EmbeddedSandboxInfo } from "./types.js";
@@ -79,3 +80,17 @@ export function createSystemPromptOverride(
   const trimmed = systemPrompt.trim();
   return () => trimmed;
 }
+
+export function applySystemPromptOverrideToSession(
+  session: AgentSession,
+  override: (defaultPrompt?: string) => string,
+) {
+  const prompt = override().trim();
+  session.agent.setSystemPrompt(prompt);
+  const mutableSession = session as unknown as {
+    _baseSystemPrompt?: string;
+    _rebuildSystemPrompt?: (toolNames: string[]) => string;
+  };
+  mutableSession._baseSystemPrompt = prompt;
+  mutableSession._rebuildSystemPrompt = () => prompt;
+}