diff --git a/packages/coding-agent/src/core/package-manager.ts b/packages/coding-agent/src/core/package-manager.ts
index e8c9f45..26410de 100644
--- a/packages/coding-agent/src/core/package-manager.ts
+++ b/packages/coding-agent/src/core/package-manager.ts
@@ -368,6 +368,47 @@ function collectAncestorAgentsSkillDirs(startDir: string): string[] {
   return skillDirs;
 }
 
+function collectCompanionWorkspaceSkillDirs(
+  startDir: string,
+  agentDir: string,
+): string[] {
+  const skillDirs: string[] = [];
+  const seen = new Set<string>();
+  const configDir = dirname(resolve(agentDir));
+  const defaultWorkspaceDir = join(configDir, "workspace");
+
+  const addDir = (dir: string): void => {
+    const skillDir = join(resolve(dir), ".agents", "skills");
+    if (seen.has(skillDir)) {
+      return;
+    }
+    skillDirs.push(skillDir);
+    seen.add(skillDir);
+  };
+
+  if (existsSync(defaultWorkspaceDir)) {
+    addDir(defaultWorkspaceDir);
+  }
+
+  let dir = resolve(startDir);
+  while (true) {
+    if (dirname(dir) === configDir) {
+      const dirName = basename(dir);
+      if (dirName === "workspace" || dirName.startsWith("workspace-")) {
+        addDir(dir);
+      }
+    }
+
+    const parent = dirname(dir);
+    if (parent === dir) {
+      break;
+    }
+    dir = parent;
+  }
+
+  return skillDirs;
+}
+
 function collectAutoPromptEntries(dir: string): string[] {
   const entries: string[] = [];
   if (!existsSync(dir)) return entries;
@@ -1897,6 +1938,10 @@ export class DefaultPackageManager implements PackageManager {
     };
     const userAgentsSkillsDir = join(homedir(), ".agents", "skills");
     const projectAgentsSkillDirs = collectAncestorAgentsSkillDirs(this.cwd);
+    const companionWorkspaceSkillDirs = collectCompanionWorkspaceSkillDirs(
+      this.cwd,
+      this.agentDir,
+    );
 
     const addResources = (
       resourceType: ResourceType,
@@ -1923,6 +1968,9 @@ export class DefaultPackageManager implements PackageManager {
       "skills",
       [
         ...collectAutoSkillEntries(projectDirs.skills),
+        ...companionWorkspaceSkillDirs.flatMap((dir) =>
+          collectAutoSkillEntries(dir),
+        ),
         ...projectAgentsSkillDirs.flatMap((dir) =>
           collectAutoSkillEntries(dir),
         ),
diff --git a/packages/coding-agent/src/core/resource-loader.ts b/packages/coding-agent/src/core/resource-loader.ts
index 938d3c6..13e5fdd 100644
--- a/packages/coding-agent/src/core/resource-loader.ts
+++ b/packages/coding-agent/src/core/resource-loader.ts
@@ -1,6 +1,6 @@
 import { existsSync, readdirSync, readFileSync, statSync } from "node:fs";
 import { homedir } from "node:os";
-import { join, resolve, sep } from "node:path";
+import { basename, dirname, join, resolve, sep } from "node:path";
 import chalk from "chalk";
 import { CONFIG_DIR_NAME, getAgentDir } from "../config.js";
 import {
@@ -120,6 +120,78 @@ function loadNamedContextFileFromDir(
   }
 }
 
+const companionContextFilenames = [
+  "IDENTITY.md",
+  "SOUL.md",
+  "USER.md",
+  "TOOLS.md",
+  "HEARTBEAT.md",
+  "MEMORY.md",
+  "BOOTSTRAP.md",
+];
+
+function loadNamedContextFilesFromDir(
+  dir: string,
+  filenames: string[],
+): Array<{ path: string; content: string }> {
+  const files: Array<{ path: string; content: string }> = [];
+  for (const filename of filenames) {
+    const file = loadNamedContextFileFromDir(dir, filename);
+    if (file) {
+      files.push(file);
+    }
+  }
+  return files;
+}
+
+function addContextFile(
+  contextFiles: Array<{ path: string; content: string }>,
+  seenPaths: Set<string>,
+  file: { path: string; content: string } | null,
+): void {
+  if (!file || seenPaths.has(file.path)) {
+    return;
+  }
+  contextFiles.push(file);
+  seenPaths.add(file.path);
+}
+
+function collectCompanionContextDirs(cwd: string, agentDir: string): string[] {
+  const contextDirs: string[] = [];
+  const seenDirs = new Set<string>();
+  const configDir = dirname(resolve(agentDir));
+  const defaultWorkspaceDir = join(configDir, "workspace");
+
+  const addDir = (dir: string): void => {
+    const resolvedDir = resolve(dir);
+    if (!existsSync(resolvedDir) || seenDirs.has(resolvedDir)) {
+      return;
+    }
+    contextDirs.push(resolvedDir);
+    seenDirs.add(resolvedDir);
+  };
+
+  addDir(defaultWorkspaceDir);
+
+  let currentDir = resolve(cwd);
+  while (true) {
+    if (dirname(currentDir) === configDir) {
+      const dirName = basename(currentDir);
+      if (dirName === "workspace" || dirName.startsWith("workspace-")) {
+        addDir(currentDir);
+      }
+    }
+
+    const parentDir = dirname(currentDir);
+    if (parentDir === currentDir) {
+      break;
+    }
+    currentDir = parentDir;
+  }
+
+  return contextDirs;
+}
+
 function loadProjectContextFiles(
   options: { cwd?: string; agentDir?: string } = {},
 ): Array<{ path: string; content: string }> {
@@ -129,11 +201,11 @@ function loadProjectContextFiles(
   const contextFiles: Array<{ path: string; content: string }> = [];
   const seenPaths = new Set<string>();
 
-  const globalContext = loadContextFileFromDir(resolvedAgentDir);
-  if (globalContext) {
-    contextFiles.push(globalContext);
-    seenPaths.add(globalContext.path);
-  }
+  addContextFile(
+    contextFiles,
+    seenPaths,
+    loadContextFileFromDir(resolvedAgentDir),
+  );
 
   const ancestorContextFiles: Array<{ path: string; content: string }> = [];
 
@@ -156,17 +228,29 @@ function loadProjectContextFiles(
 
   contextFiles.push(...ancestorContextFiles);
 
-  const globalSoul = loadNamedContextFileFromDir(resolvedAgentDir, "SOUL.md");
-  if (globalSoul && !seenPaths.has(globalSoul.path)) {
-    contextFiles.push(globalSoul);
-    seenPaths.add(globalSoul.path);
+  addContextFile(
+    contextFiles,
+    seenPaths,
+    loadNamedContextFileFromDir(resolvedAgentDir, "SOUL.md"),
+  );
+
+  for (const companionDir of collectCompanionContextDirs(
+    resolvedCwd,
+    resolvedAgentDir,
+  )) {
+    for (const file of loadNamedContextFilesFromDir(
+      companionDir,
+      companionContextFilenames,
+    )) {
+      addContextFile(contextFiles, seenPaths, file);
+    }
   }
 
-  const projectSoul = loadNamedContextFileFromDir(resolvedCwd, "SOUL.md");
-  if (projectSoul && !seenPaths.has(projectSoul.path)) {
-    contextFiles.push(projectSoul);
-    seenPaths.add(projectSoul.path);
-  }
+  addContextFile(
+    contextFiles,
+    seenPaths,
+    loadNamedContextFileFromDir(resolvedCwd, "SOUL.md"),
+  );
 
   return contextFiles;
 }
diff --git a/packages/coding-agent/src/core/system-prompt.ts b/packages/coding-agent/src/core/system-prompt.ts
index 9fb37ac..4098bbe 100644
--- a/packages/coding-agent/src/core/system-prompt.ts
+++ b/packages/coding-agent/src/core/system-prompt.ts
@@ -49,12 +49,42 @@ function buildProjectContextSection(
     ({ path }) =>
       path.replaceAll("\\", "/").endsWith("/SOUL.md") || path === "SOUL.md",
   );
+  const hasContextFile = (filename: string) =>
+    contextFiles.some(
+      ({ path }) =>
+        path.replaceAll("\\", "/").endsWith(`/${filename}`) ||
+        path === filename,
+    );
   let section = "\n\n# Project Context\n\n";
   section += "Project-specific instructions and guidelines:\n";
   if (hasSoulFile) {
     section +=
       "\nIf SOUL.md is present, embody its persona and tone. Avoid generic assistant filler and follow its guidance unless higher-priority instructions override it.\n";
   }
+  if (hasContextFile("IDENTITY.md")) {
+    section +=
+      "\nIf IDENTITY.md is present, treat it as the agent's self-description and stay consistent with it.\n";
+  }
+  if (hasContextFile("USER.md")) {
+    section +=
+      "\nIf USER.md is present, use it as durable context about the user and avoid re-asking for facts already captured there.\n";
+  }
+  if (hasContextFile("MEMORY.md")) {
+    section +=
+      "\nIf MEMORY.md is present, use it as long-term memory and keep it aligned with durable user or project context when the task calls for it.\n";
+  }
+  if (hasContextFile("TOOLS.md")) {
+    section +=
+      "\nIf TOOLS.md is present, treat it as the source of truth for the current sandbox filesystem, app locations, and environment-specific workflow details.\n";
+  }
+  if (hasContextFile("HEARTBEAT.md")) {
+    section +=
+      "\nIf HEARTBEAT.md is present, honor it as recurring operational guidance for the agent.\n";
+  }
+  if (hasContextFile("BOOTSTRAP.md")) {
+    section +=
+      "\nIf BOOTSTRAP.md is present, treat it as an actionable onboarding task list and execute it before drifting into unrelated work.\n";
+  }
   section += "\n";
   for (const { path: filePath, content } of contextFiles) {
     section += `## ${filePath}\n\n${content}\n\n`;
diff --git a/packages/coding-agent/test/package-manager.test.ts b/packages/coding-agent/test/package-manager.test.ts
index c3e10d7..5c84157 100644
--- a/packages/coding-agent/test/package-manager.test.ts
+++ b/packages/coding-agent/test/package-manager.test.ts
@@ -322,6 +322,38 @@ Content`,
         result.skills.some((r) => r.path === middleSkill && r.enabled),
       ).toBe(true);
     });
+
+    it("should include default workspace skills when cwd is outside the workspace root", async () => {
+      const workspaceSkill = join(
+        tempDir,
+        "workspace",
+        ".agents",
+        "skills",
+        "build-app",
+        "SKILL.md",
+      );
+      mkdirSync(join(tempDir, "workspace", ".agents", "skills", "build-app"), {
+        recursive: true,
+      });
+      writeFileSync(
+        workspaceSkill,
+        "---\nname: build-app\ndescription: Build apps\n---\n",
+      );
+
+      const appCwd = join(tempDir, "apps", "portfolio");
+      mkdirSync(appCwd, { recursive: true });
+
+      const pm = new DefaultPackageManager({
+        cwd: appCwd,
+        agentDir,
+        settingsManager,
+      });
+
+      const result = await pm.resolve();
+      expect(
+        result.skills.some((r) => r.path === workspaceSkill && r.enabled),
+      ).toBe(true);
+    });
   });
 
   describe("ignore files", () => {
diff --git a/packages/coding-agent/test/resource-loader.test.ts b/packages/coding-agent/test/resource-loader.test.ts
index 6a2b07f..6b9253f 100644
--- a/packages/coding-agent/test/resource-loader.test.ts
+++ b/packages/coding-agent/test/resource-loader.test.ts
@@ -320,6 +320,28 @@ Content`,
       expect(agentsFiles.some((f) => f.path.endsWith("SOUL.md"))).toBe(true);
     });
 
+    it("should discover companion context files from the default workspace", async () => {
+      const workspaceDir = join(tempDir, "workspace");
+      const appDir = join(tempDir, "apps", "todo-app");
+      mkdirSync(workspaceDir, { recursive: true });
+      mkdirSync(appDir, { recursive: true });
+      writeFileSync(join(workspaceDir, "IDENTITY.md"), "# Identity\n\nPi");
+      writeFileSync(join(workspaceDir, "TOOLS.md"), "# Tools\n\nUse ~/.pi");
+      writeFileSync(join(workspaceDir, "BOOTSTRAP.md"), "# Bootstrap\n\nDo it");
+
+      const loader = new DefaultResourceLoader({ cwd: appDir, agentDir });
+      await loader.reload();
+
+      const { agentsFiles } = loader.getAgentsFiles();
+      expect(agentsFiles.some((f) => f.path.endsWith("IDENTITY.md"))).toBe(
+        true,
+      );
+      expect(agentsFiles.some((f) => f.path.endsWith("TOOLS.md"))).toBe(true);
+      expect(agentsFiles.some((f) => f.path.endsWith("BOOTSTRAP.md"))).toBe(
+        true,
+      );
+    });
+
     it("should discover SYSTEM.md from cwd/.pi", async () => {
       const piDir = join(cwd, ".pi");
       mkdirSync(piDir, { recursive: true });
diff --git a/packages/coding-agent/test/system-prompt.test.ts b/packages/coding-agent/test/system-prompt.test.ts
index c4cbf72..e9013f9 100644
--- a/packages/coding-agent/test/system-prompt.test.ts
+++ b/packages/coding-agent/test/system-prompt.test.ts
@@ -100,5 +100,35 @@ describe("buildSystemPrompt", () => {
       );
       expect(prompt).toContain("## /tmp/project/SOUL.md");
     });
+
+    test("adds companion context guidance for identity, tools, and bootstrap files", () => {
+      const prompt = buildSystemPrompt({
+        contextFiles: [
+          {
+            path: "/home/node/.pi/workspace/IDENTITY.md",
+            content: "# Identity\n\nPi",
+          },
+          {
+            path: "/home/node/.pi/workspace/TOOLS.md",
+            content: "# Tools\n\nUse ~/.pi/apps",
+          },
+          {
+            path: "/home/node/.pi/workspace/BOOTSTRAP.md",
+            content: "# Bootstrap\n\nDo the setup",
+          },
+        ],
+        skills: [],
+      });
+
+      expect(prompt).toContain(
+        "If IDENTITY.md is present, treat it as the agent's self-description",
+      );
+      expect(prompt).toContain(
+        "If TOOLS.md is present, treat it as the source of truth for the current sandbox filesystem",
+      );
+      expect(prompt).toContain(
+        "If BOOTSTRAP.md is present, treat it as an actionable onboarding task list",
+      );
+    });
   });
 });