From 1edebb1b048f278512ea8391fd7cb290e8fa1987 Mon Sep 17 00:00:00 2001
From: Federico Jaramillo Martinez <federicojaramillom@gmail.com>
Date: Mon, 29 Jun 2026 07:56:01 +0200
Subject: [PATCH] fix: require explicit alternate agent state

---
 docs/config.html                              | 35 ++++++-------
 docs/config.md                                | 20 ++++----
 src/cli.test.ts                               |  6 +--
 .../settings/SettingsSessiondPanel.ts         |  4 +-
 src/config.test.ts                            | 51 +++++++++++--------
 src/config.ts                                 | 30 +++++++----
 src/server/configRoutes.ts                    |  9 ++--
 7 files changed, 88 insertions(+), 67 deletions(-)

diff --git a/docs/config.html b/docs/config.html
index 5d89c2d..5a4f7c6 100644
--- a/docs/config.html
+++ b/docs/config.html
@@ -130,8 +130,8 @@
               <p>
                 Environment overrides include <code>PI_WEB_HOST</code>, <code>PI_WEB_PORT</code> / <code>PORT</code>,
                 <code>PI_WEB_ALLOWED_HOSTS</code>, <code>PI_WEB_MAX_UPLOAD_BYTES</code>, <code>PI_WEB_AGENT_COMMAND</code>,
-                <code>PI_WEB_AGENT_DIR</code>, <code>PI_WEB_AGENT_SESSION_DIR</code>, <code>PI_CODING_AGENT_DIR</code>,
-                <code>PI_CODING_AGENT_SESSION_DIR</code>, <code>PI_WEB_SPAWN_SESSIONS</code>, and
+                <code>PI_WEB_AGENT_DIR</code>, <code>PI_WEB_AGENT_SESSION_DIR</code>, <code>PI_CODING_AGENT_DIR</code> /
+                <code>PI_CODING_AGENT_SESSION_DIR</code> for Pi compatibility, <code>PI_WEB_SPAWN_SESSIONS</code>, and
                 <code>PI_WEB_SUBSESSIONS</code>.
               </p>
               <ul>
@@ -280,7 +280,7 @@
                     <tr>
                       <td>Agent state directory</td>
                       <td><code>agent.dir</code></td>
-                      <td><code>PI_WEB_AGENT_DIR</code>, <code>PI_CODING_AGENT_DIR</code></td>
+                      <td><code>PI_WEB_AGENT_DIR</code> (<code>PI_CODING_AGENT_DIR</code> for Pi compatibility)</td>
                       <td>Global/session daemon</td>
                       <td>Not supported locally</td>
                       <td>Restart session daemon; affects auth, models, settings, and sessions</td>
@@ -393,7 +393,7 @@
                     <tr>
                       <td>Agent session storage directory</td>
                       <td>—</td>
-                      <td><code>PI_WEB_AGENT_SESSION_DIR</code>, <code>PI_CODING_AGENT_SESSION_DIR</code></td>
+                      <td><code>PI_WEB_AGENT_SESSION_DIR</code> (<code>PI_CODING_AGENT_SESSION_DIR</code> for Pi compatibility)</td>
                       <td>Session daemon env</td>
                       <td>Not supported locally</td>
                       <td>Restart session daemon; env-only session storage override</td>
@@ -401,7 +401,7 @@
                     <tr>
                       <td>Agent config directory</td>
                       <td>—</td>
-                      <td><code>PI_WEB_AGENT_DIR</code>, <code>PI_CODING_AGENT_DIR</code></td>
+                      <td><code>PI_WEB_AGENT_DIR</code> (<code>PI_CODING_AGENT_DIR</code> for Pi compatibility)</td>
                       <td>Web/API + session daemon env</td>
                       <td>Not supported locally</td>
                       <td>Restart services</td>
@@ -452,31 +452,32 @@
               </p>
               <p>
                 <code>agent.dir</code> controls which compatible agent state directory PI WEB reads for auth providers,
-                model settings, settings, and session metadata. It defaults to <code>~/.pi/agent</code>. Set it to another
-                Pi-compatible state directory when you want an isolated profile or an alternate compatible agent's data.
+                model settings, settings, and session metadata. It defaults to <code>~/.pi/agent</code> only for the default
+                <code>pi</code> command. Set it explicitly when you want an isolated Pi profile or when
+                <code>agent.command</code> points at another compatible CLI.
               </p>
               <div class="code-card">
                 <pre><code>{
   "agent": {
-    "command": "pi",
-    "dir": "~/agent-profiles/research"
+    "command": "my-pi-fork",
+    "dir": "/opt/my-pi-fork/agent"
   }
 }</code></pre>
               </div>
               <p>
-                For example, an Oh My Pi profile can set <code>agent.command</code> to <code>omp</code> and
-                <code>agent.dir</code> to <code>~/.omp/agent</code>.
+                For example, a fork profile can set <code>agent.command</code> to <code>my-pi-fork</code> and
+                <code>agent.dir</code> to <code>/opt/my-pi-fork/agent</code>.
               </p>
               <p>
                 Environment variables take precedence over the config file. <code>PI_WEB_AGENT_COMMAND</code> selects the
-                command, <code>PI_WEB_AGENT_DIR</code> sets the state directory for any command, and
-                <code>PI_WEB_AGENT_SESSION_DIR</code> overrides session storage separately from <code>agent.dir</code>.
-                Existing Pi Coding Agent env names (<code>PI_CODING_AGENT_DIR</code> and
-                <code>PI_CODING_AGENT_SESSION_DIR</code>) remain supported for compatibility.
+                command, <code>PI_WEB_AGENT_DIR</code> sets the state directory, and <code>PI_WEB_AGENT_SESSION_DIR</code>
+                overrides session storage separately from <code>agent.dir</code>. Existing Pi Coding Agent env names
+                (<code>PI_CODING_AGENT_DIR</code> and <code>PI_CODING_AGENT_SESSION_DIR</code>) remain supported only for
+                Pi compatibility; alternate commands should use the explicit PI WEB variables or config keys.
               </p>
               <p>
-                Session directory overrides are environment-only; use <code>PI_WEB_AGENT_SESSION_DIR</code> unless you need
-                the legacy Pi-compatible <code>PI_CODING_AGENT_SESSION_DIR</code> name.
+                Session directory overrides are environment-only; use <code>PI_WEB_AGENT_SESSION_DIR</code> unless you are
+                intentionally using the legacy Pi-compatible <code>PI_CODING_AGENT_SESSION_DIR</code> name.
               </p>
               <div class="callout warning">
                 Restart the session daemon after changing agent settings. The web/API process can display the new config
diff --git a/docs/config.md b/docs/config.md
index 22429fc..8baf495 100644
--- a/docs/config.md
+++ b/docs/config.md
@@ -25,7 +25,7 @@ defaults → global config file → environment overrides
 
 Supported project-local settings are then applied for that project's workspaces. For upload defaults, `<project>/.pi-web/config.json` overrides the global value.
 
-Environment overrides include `PI_WEB_HOST`, `PI_WEB_PORT` / `PORT`, `PI_WEB_ALLOWED_HOSTS`, `PI_WEB_MAX_UPLOAD_BYTES`, `PI_WEB_AGENT_COMMAND`, `PI_WEB_AGENT_DIR`, `PI_WEB_AGENT_SESSION_DIR`, `PI_CODING_AGENT_DIR`, `PI_CODING_AGENT_SESSION_DIR`, `PI_WEB_SPAWN_SESSIONS`, and `PI_WEB_SUBSESSIONS`.
+Environment overrides include `PI_WEB_HOST`, `PI_WEB_PORT` / `PORT`, `PI_WEB_ALLOWED_HOSTS`, `PI_WEB_MAX_UPLOAD_BYTES`, `PI_WEB_AGENT_COMMAND`, `PI_WEB_AGENT_DIR`, `PI_WEB_AGENT_SESSION_DIR`, `PI_CODING_AGENT_DIR` / `PI_CODING_AGENT_SESSION_DIR` for Pi compatibility, `PI_WEB_SPAWN_SESSIONS`, and `PI_WEB_SUBSESSIONS`.
 
 Process restarts depend on the key:
 
@@ -104,7 +104,7 @@ Rows with JSON key `—` are runtime-only environment variables, not config-file
 | Manual file upload default folder | `uploads.defaultFolder` | — | Global + project | **Overrides**: project value wins for workspaces in that project; otherwise global/default applies | New Upload dialogs and direct drag/drop batches after config/workspace refresh |
 | Upload/body limit | `maxUploadBytes` | `PI_WEB_MAX_UPLOAD_BYTES` | Global | Not supported locally | Restart web/API and session daemon |
 | Agent CLI command | `agent.command` | `PI_WEB_AGENT_COMMAND` | Global/session daemon | Not supported locally | Restart session daemon; affects doctor/status/update checks |
-| Agent state directory | `agent.dir` | `PI_WEB_AGENT_DIR`, `PI_CODING_AGENT_DIR` | Global/session daemon | Not supported locally | Restart session daemon; affects auth, models, settings, and sessions |
+| Agent state directory | `agent.dir` | `PI_WEB_AGENT_DIR` (`PI_CODING_AGENT_DIR` for Pi compatibility) | Global/session daemon | Not supported locally | Restart session daemon; affects auth, models, settings, and sessions |
 | Agent can spawn sessions | `spawnSessions` | `PI_WEB_SPAWN_SESSIONS` | Global/session daemon | Not supported locally | Restart session daemon |
 | Tracked subsessions (beta) | `subsessions` | `PI_WEB_SUBSESSIONS` | Global/session daemon | Not supported locally; also requires `spawnSessions` | Restart session daemon |
 | Plugin enablement/settings | `plugins.<id>.enabled`, `plugins.<id>.settings` | — | Global | Not core local config; plugins may read their own project files | Reload browser tab |
@@ -119,8 +119,8 @@ Rows with JSON key `—` are runtime-only environment variables, not config-file
 | Web-to-daemon URL | — | `PI_WEB_SESSIOND_URL` | Web/API env | Not supported locally | Restart web/API |
 | Projects storage file | — | `PI_WEB_PROJECTS_FILE` | Web/API + session daemon env | Not supported locally | Restart services; advanced state override |
 | Remote machines storage file | — | `PI_WEB_MACHINES_FILE` | Web/API env | Not supported locally | Restart web/API; advanced state override |
-| Agent session storage directory | — | `PI_WEB_AGENT_SESSION_DIR`, `PI_CODING_AGENT_SESSION_DIR` | Session daemon env | Not supported locally | Restart session daemon; env-only session storage override |
-| Agent config directory | — | `PI_WEB_AGENT_DIR`, `PI_CODING_AGENT_DIR` | Web/API + session daemon env | Not supported locally | Restart services |
+| Agent session storage directory | — | `PI_WEB_AGENT_SESSION_DIR` (`PI_CODING_AGENT_SESSION_DIR` for Pi compatibility) | Session daemon env | Not supported locally | Restart session daemon; env-only session storage override |
+| Agent config directory | — | `PI_WEB_AGENT_DIR` (`PI_CODING_AGENT_DIR` for Pi compatibility) | Web/API + session daemon env | Not supported locally | Restart services |
 | Skip update checks | — | `PI_WEB_SKIP_VERSION_CHECK`, `PI_WEB_OFFLINE`, `PI_SKIP_VERSION_CHECK`, `PI_OFFLINE` | Web/API env | Not supported locally | Restart web/API after env changes |
 
 ## Key details
@@ -170,22 +170,22 @@ The per-request size limit is still controlled by `maxUploadBytes` / `PI_WEB_MAX
 
 `agent.command` controls which Pi-compatible CLI PI WEB checks in doctor/status/update flows. It defaults to `pi`. Set it only when diagnostics and package-managed update checks should target another compatible command; the embedded session runtime still uses PI WEB's SDK integration.
 
-`agent.dir` controls which compatible agent state directory PI WEB reads for auth providers, model settings, settings, and session metadata. It defaults to `~/.pi/agent`. Set it to another Pi-compatible state directory when you want an isolated profile or an alternate compatible agent's data.
+`agent.dir` controls which compatible agent state directory PI WEB reads for auth providers, model settings, settings, and session metadata. It defaults to `~/.pi/agent` only for the default `pi` command. Set it explicitly when you want an isolated Pi profile or when `agent.command` points at another compatible CLI.
 
 ```json
 {
   "agent": {
-    "command": "pi",
-    "dir": "~/agent-profiles/research"
+    "command": "my-pi-fork",
+    "dir": "/opt/my-pi-fork/agent"
   }
 }
 ```
 
-For example, an Oh My Pi profile can set `agent.command` to `omp` and `agent.dir` to `~/.omp/agent`.
+For example, a fork profile can set `agent.command` to `my-pi-fork` and `agent.dir` to `/opt/my-pi-fork/agent`.
 
-Environment variables take precedence over the config file. `PI_WEB_AGENT_COMMAND` selects the command, `PI_WEB_AGENT_DIR` sets the state directory for any command, and `PI_WEB_AGENT_SESSION_DIR` overrides session storage separately from `agent.dir`. Existing Pi Coding Agent env names (`PI_CODING_AGENT_DIR` and `PI_CODING_AGENT_SESSION_DIR`) remain supported for compatibility.
+Environment variables take precedence over the config file. `PI_WEB_AGENT_COMMAND` selects the command, `PI_WEB_AGENT_DIR` sets the state directory, and `PI_WEB_AGENT_SESSION_DIR` overrides session storage separately from `agent.dir`. Existing Pi Coding Agent env names (`PI_CODING_AGENT_DIR` and `PI_CODING_AGENT_SESSION_DIR`) remain supported only for Pi compatibility; alternate commands should use the explicit PI WEB variables or config keys.
 
-Session directory overrides are environment-only; use `PI_WEB_AGENT_SESSION_DIR` unless you need the legacy Pi-compatible `PI_CODING_AGENT_SESSION_DIR` name.
+Session directory overrides are environment-only; use `PI_WEB_AGENT_SESSION_DIR` unless you are intentionally using the legacy Pi-compatible `PI_CODING_AGENT_SESSION_DIR` name.
 
 Restart the session daemon after changing agent settings. The web/API process can display the new config immediately, and status/plugin discovery may re-read it on later requests, but active session runtime ownership is intentionally long-lived.
 
diff --git a/src/cli.test.ts b/src/cli.test.ts
index 065e55a..be297be 100644
--- a/src/cli.test.ts
+++ b/src/cli.test.ts
@@ -46,7 +46,7 @@ describe("commandWithVersionCheck", () => {
 
   it("shell-quotes command words", () => {
     process.env["SHELL"] = "/bin/bash";
-    expect(commandWithVersionCheck("/tmp/agent's/omp")).toBe("command -v '/tmp/agent'\\''s/omp' && ('/tmp/agent'\\''s/omp' --version 2>&1 || true)");
+    expect(commandWithVersionCheck("/tmp/agent's/acme-agent")).toBe("command -v '/tmp/agent'\\''s/acme-agent' && ('/tmp/agent'\\''s/acme-agent' --version 2>&1 || true)");
   });
 });
 
@@ -55,11 +55,11 @@ describe("agentCommandForChecks", () => {
     const dir = mkdtempSync(join(tmpdir(), "pi-web-cli-test-"));
     try {
       const configPath = join(dir, "config.json");
-      writeFileSync(configPath, `${JSON.stringify({ agent: { command: "omp" } })}\n`);
+      writeFileSync(configPath, `${JSON.stringify({ agent: { command: "acme-agent", dir: "/opt/acme-agent/state" } })}\n`);
       process.env["PI_WEB_CONFIG"] = configPath;
       delete process.env["PI_WEB_AGENT_COMMAND"];
 
-      expect(agentCommandForChecks()).toBe("omp");
+      expect(agentCommandForChecks()).toBe("acme-agent");
     } finally {
       rmSync(dir, { recursive: true, force: true });
     }
diff --git a/src/client/src/components/settings/SettingsSessiondPanel.ts b/src/client/src/components/settings/SettingsSessiondPanel.ts
index 4ac2e31..7a48a6c 100644
--- a/src/client/src/components/settings/SettingsSessiondPanel.ts
+++ b/src/client/src/components/settings/SettingsSessiondPanel.ts
@@ -71,7 +71,7 @@ export class SettingsSessiondPanel extends LitElement {
             ?disabled=${this.loading || this.saving || agentDirOverridden}
             @change=${(event: Event) => { void this.saveAgentField("dir", event); }}
           >
-          <small>Choose which compatible auth, models, settings, and sessions PI WEB reads. Set a separate directory for isolated agent profiles, then restart the session daemon.</small>
+          <small>Choose which compatible auth, models, settings, and sessions PI WEB reads. Non-<code>pi</code> commands require an explicit state directory, then a session daemon restart.</small>
         </div>
         <div class="field">
           <span class="field-heading">
@@ -110,7 +110,7 @@ export class SettingsSessiondPanel extends LitElement {
           <h3>Effective after environment overrides</h3>
           <dl>
             <div><dt>Agent command</dt><dd>${effectiveAgent?.command ?? html`<span class="muted">pi default</span>`}</dd></div>
-            <div><dt>Agent state</dt><dd>${effectiveAgent?.dir ?? html`<span class="muted">Pi default</span>`}</dd></div>
+            <div><dt>Agent state</dt><dd>${effectiveAgent?.dir ?? html`<span class="muted">~/.pi/agent default</span>`}</dd></div>
             <div><dt>Spawn sessions</dt><dd>${effectiveSpawn ? "Enabled" : html`<span class="muted">Disabled</span>`}</dd></div>
             <div><dt>Subsessions</dt><dd>${effectiveSubsessions ? "Enabled" : html`<span class="muted">Disabled</span>`}</dd></div>
           </dl>
diff --git a/src/config.test.ts b/src/config.test.ts
index a1352b7..8d53aa4 100644
--- a/src/config.test.ts
+++ b/src/config.test.ts
@@ -50,23 +50,28 @@ describe("PI WEB config persistence", () => {
   });
 
   it("persists and reads custom agent runtime settings", () => {
-    savePiWebConfig({ agent: { command: "omp", dir: "~/.omp/agent" } }, testOptions());
+    savePiWebConfig({ agent: { command: "acme-agent", dir: "/opt/acme-agent/state" } }, testOptions());
 
-    expect(loadPiWebConfig(testOptions()).config.agent).toEqual({ command: "omp", dir: "~/.omp/agent" });
+    expect(loadPiWebConfig(testOptions()).config.agent).toEqual({ command: "acme-agent", dir: "/opt/acme-agent/state" });
   });
 
-  it("keeps the Pi agent directory default for alternate commands", () => {
-    expect(effectiveAgentConfig({ HOME: join(tempDir, ".home") }, { agent: { command: "omp" } })).toMatchObject({
-      command: "omp",
+  it("defaults to the Pi agent directory only for Pi commands and launchers", () => {
+    expect(effectiveAgentConfig({ HOME: join(tempDir, ".home") }, { agent: { command: "/tmp/pi.cmd" } })).toMatchObject({
+      command: "/tmp/pi.cmd",
       dir: join(tempDir, ".home", ".pi", "agent"),
       sessionDirEnvKeys: ["PI_WEB_AGENT_SESSION_DIR", "PI_CODING_AGENT_SESSION_DIR"],
     });
   });
 
+  it("requires an explicit agent directory for non-Pi commands", () => {
+    expect(() => effectiveAgentConfig({}, { agent: { command: "acme-agent" } })).toThrow('PI WEB config agent.dir or PI_WEB_AGENT_DIR is required when agent.command is "acme-agent"');
+    expect(() => savePiWebConfig({ agent: { command: "acme-agent" } }, testOptions())).toThrow('PI WEB config agent.dir or PI_WEB_AGENT_DIR is required when agent.command is "acme-agent"');
+  });
+
   it("resolves explicit alternate agent command and state directory settings", () => {
-    expect(effectiveAgentConfig({ HOME: join(tempDir, ".home") }, { agent: { command: "omp", dir: "~/.omp/agent" } })).toMatchObject({
-      command: "omp",
-      dir: join(tempDir, ".home", ".omp", "agent"),
+    expect(effectiveAgentConfig({ HOME: join(tempDir, ".home") }, { agent: { command: "acme-agent", dir: "~/agent-profiles/acme" } })).toMatchObject({
+      command: "acme-agent",
+      dir: join(tempDir, ".home", "agent-profiles", "acme"),
     });
   });
 
@@ -80,36 +85,40 @@ describe("PI WEB config persistence", () => {
       PI_CODING_AGENT_SESSION_DIR: "",
     };
 
-    expect(effectiveAgentConfig(env, { agent: { command: "omp", dir: "~/.omp/agent" } })).toMatchObject({
-      command: "omp",
-      dir: join(tempDir, ".home", ".omp", "agent"),
+    expect(effectiveAgentConfig(env, { agent: { command: "acme-agent", dir: "~/agent-profiles/acme" } })).toMatchObject({
+      command: "acme-agent",
+      dir: join(tempDir, ".home", "agent-profiles", "acme"),
     });
-    expect(hasAgentDirEnvOverride(env)).toBe(false);
-    expect(hasAgentSessionDirEnvOverride(env)).toBe(false);
+    expect(hasAgentDirEnvOverride(env, "acme-agent")).toBe(false);
+    expect(hasAgentSessionDirEnvOverride(env, "acme-agent")).toBe(false);
   });
 
-  it("uses generic agent directory env precedence and Pi compatibility fallback", () => {
+  it("uses explicit PI WEB agent directory env precedence", () => {
     expect(effectiveAgentConfig({
-      PI_WEB_AGENT_COMMAND: "omp",
+      PI_WEB_AGENT_COMMAND: "acme-agent",
       PI_WEB_AGENT_DIR: join(tempDir, "web-env-agent"),
       PI_CODING_AGENT_DIR: join(tempDir, "pi-env-agent"),
     }, { agent: { command: "pi", dir: join(tempDir, "config-agent") } })).toMatchObject({
-      command: "omp",
+      command: "acme-agent",
       dir: join(tempDir, "web-env-agent"),
     });
+  });
 
+  it("keeps legacy Pi env directory overrides scoped to Pi commands", () => {
     expect(effectiveAgentConfig({
       PI_CODING_AGENT_DIR: join(tempDir, "pi-env-agent"),
     }, { agent: { dir: join(tempDir, "config-agent") } })).toMatchObject({
       dir: join(tempDir, "pi-env-agent"),
     });
+
+    expect(() => effectiveAgentConfig({
+      PI_CODING_AGENT_DIR: join(tempDir, "pi-env-agent"),
+    }, { agent: { command: "acme-agent" } })).toThrow('PI WEB config agent.dir or PI_WEB_AGENT_DIR is required when agent.command is "acme-agent"');
   });
 
-  it("does not generate command-specific session directory env keys", () => {
-    const keys = ["PI_WEB_AGENT_SESSION_DIR", "PI_CODING_AGENT_SESSION_DIR"];
-
-    expect(agentSessionDirEnvKeys()).toEqual(keys);
-    expect(effectiveAgentConfig({ HOME: join(tempDir, ".home"), PI_WEB_AGENT_COMMAND: "omp" }).sessionDirEnvKeys).toEqual(keys);
+  it("uses only explicit session directory env keys", () => {
+    expect(agentSessionDirEnvKeys()).toEqual(["PI_WEB_AGENT_SESSION_DIR", "PI_CODING_AGENT_SESSION_DIR"]);
+    expect(effectiveAgentConfig({ HOME: join(tempDir, ".home"), PI_WEB_AGENT_COMMAND: "acme-agent", PI_WEB_AGENT_DIR: join(tempDir, "agent") }).sessionDirEnvKeys).toEqual(["PI_WEB_AGENT_SESSION_DIR"]);
   });
 
   it("exposes the default upload folder in the effective config", () => {
diff --git a/src/config.ts b/src/config.ts
index b775191..55affd9 100644
--- a/src/config.ts
+++ b/src/config.ts
@@ -50,24 +50,27 @@ export interface EffectivePiWebAgentConfig {
 
 export function effectiveAgentConfig(env: NodeJS.ProcessEnv = process.env, config: Pick<PiWebConfig, "agent"> = {}, cwd = process.cwd()): EffectivePiWebAgentConfig {
   const command = parseAgentCommand(envValue(env, PI_WEB_AGENT_COMMAND_ENV) ?? config.agent?.command ?? DEFAULT_AGENT_COMMAND, "agent.command", "environment");
-  const configuredDir = envValue(env, PI_WEB_AGENT_DIR_ENV) ?? envValue(env, PI_CODING_AGENT_DIR_ENV) ?? config.agent?.dir ?? defaultAgentDir(env);
+  const configuredDir = envValue(env, PI_WEB_AGENT_DIR_ENV) ?? (isPiCommand(command) ? envValue(env, PI_CODING_AGENT_DIR_ENV) : undefined) ?? config.agent?.dir ?? defaultAgentDirForCommand(command, env);
   return {
     command,
     dir: resolveAgentDirPath(configuredDir, env, cwd, "agent.dir", "environment"),
-    sessionDirEnvKeys: agentSessionDirEnvKeys(),
+    sessionDirEnvKeys: agentSessionDirEnvKeys(command),
   };
 }
 
-export function agentSessionDirEnvKeys(): string[] {
-  return uniqueStrings([PI_WEB_AGENT_SESSION_DIR_ENV, PI_CODING_AGENT_SESSION_DIR_ENV]);
+export function agentSessionDirEnvKeys(command = DEFAULT_AGENT_COMMAND): string[] {
+  return uniqueStrings([
+    PI_WEB_AGENT_SESSION_DIR_ENV,
+    ...(isPiCommand(command) ? [PI_CODING_AGENT_SESSION_DIR_ENV] : []),
+  ]);
 }
 
-export function hasAgentDirEnvOverride(env: NodeJS.ProcessEnv): boolean {
-  return isEnvSet(env[PI_WEB_AGENT_DIR_ENV]) || isEnvSet(env[PI_CODING_AGENT_DIR_ENV]);
+export function hasAgentDirEnvOverride(env: NodeJS.ProcessEnv, command = DEFAULT_AGENT_COMMAND): boolean {
+  return isEnvSet(env[PI_WEB_AGENT_DIR_ENV]) || (isPiCommand(command) && isEnvSet(env[PI_CODING_AGENT_DIR_ENV]));
 }
 
-export function hasAgentSessionDirEnvOverride(env: NodeJS.ProcessEnv): boolean {
-  return agentSessionDirEnvKeys().some((key) => isEnvSet(env[key]));
+export function hasAgentSessionDirEnvOverride(env: NodeJS.ProcessEnv, command = DEFAULT_AGENT_COMMAND): boolean {
+  return agentSessionDirEnvKeys(command).some((key) => isEnvSet(env[key]));
 }
 
 export function effectiveUploadsConfig(config: Pick<PiWebConfig, "uploads"> = {}): NonNullable<PiWebConfig["uploads"]> {
@@ -141,6 +144,7 @@ export function savePiWebConfig(config: PiWebConfig, options: LoadOptions = {}):
   const env = options.env ?? process.env;
   const path = piWebConfigPath(env, options.cwd ?? process.cwd());
   const normalized = parsePiWebConfig(piWebConfigRecord(config), path);
+  effectiveAgentConfig(env, normalized, options.cwd ?? process.cwd());
   const existing = readExistingConfigObject(path);
   delete existing["host"];
   delete existing["port"];
@@ -335,8 +339,14 @@ function expandHomePath(value: string, env: NodeJS.ProcessEnv): string {
   return value;
 }
 
-function defaultAgentDir(env: NodeJS.ProcessEnv): string {
-  return expandHomePath("~/.pi/agent", env);
+function defaultAgentDirForCommand(command: string, env: NodeJS.ProcessEnv): string {
+  if (isPiCommand(command)) return expandHomePath("~/.pi/agent", env);
+  throw new Error(`PI WEB config agent.dir or ${PI_WEB_AGENT_DIR_ENV} is required when agent.command is ${JSON.stringify(command)}`);
+}
+
+function isPiCommand(command: string): boolean {
+  const name = command.split(/[\\/]/u).at(-1)?.toLowerCase() ?? command.toLowerCase();
+  return name.replace(/(?:\.[cm]?js|\.exe|\.cmd)$/iu, "") === DEFAULT_AGENT_COMMAND;
 }
 
 function envValue(env: NodeJS.ProcessEnv, key: string): string | undefined {
diff --git a/src/server/configRoutes.ts b/src/server/configRoutes.ts
index 838e6ee..14b52dc 100644
--- a/src/server/configRoutes.ts
+++ b/src/server/configRoutes.ts
@@ -27,7 +27,7 @@ export function currentPiWebConfigResponse(options: LoadOptions = {}): PiWebConf
     exists: loaded.exists,
     config: loaded.config,
     effectiveConfig: effective.config,
-    envOverrides: piWebConfigEnvOverrides(env),
+    envOverrides: piWebConfigEnvOverrides(env, effective.config),
   };
 }
 
@@ -167,7 +167,8 @@ function parsePluginsRequest(value: unknown): NonNullable<PiWebConfig["plugins"]
   }));
 }
 
-function piWebConfigEnvOverrides(env: NodeJS.ProcessEnv): PiWebConfigEnvOverrides {
+function piWebConfigEnvOverrides(env: NodeJS.ProcessEnv, config: PiWebConfig = {}): PiWebConfigEnvOverrides {
+  const command = config.agent?.command;
   return {
     host: isEnvSet(env["PI_WEB_HOST"]),
     port: isEnvSet(env["PI_WEB_PORT"]) || isEnvSet(env["PORT"]),
@@ -175,8 +176,8 @@ function piWebConfigEnvOverrides(env: NodeJS.ProcessEnv): PiWebConfigEnvOverride
     spawnSessions: isEnvSet(env["PI_WEB_SPAWN_SESSIONS"]),
     subsessions: isEnvSet(env["PI_WEB_SUBSESSIONS"]),
     agentCommand: isEnvSet(env["PI_WEB_AGENT_COMMAND"]),
-    agentDir: hasAgentDirEnvOverride(env),
-    agentSessionDir: hasAgentSessionDirEnvOverride(env),
+    agentDir: hasAgentDirEnvOverride(env, command),
+    agentSessionDir: hasAgentSessionDirEnvOverride(env, command),
   };
 }