diff --git a/crates/op-host-desktop/src/app_handler.rs b/crates/op-host-desktop/src/app_handler.rs
index fe27f3ba2..e185fd764 100644
--- a/crates/op-host-desktop/src/app_handler.rs
+++ b/crates/op-host-desktop/src/app_handler.rs
@@ -230,6 +230,10 @@ impl ApplicationHandler for DesktopApp {
         // first paint so the launch document shows immediately.
         self.drain_opened_files();
 
+        if self.bootstrap_mcp_runtime_from_settings() {
+            settings_io::save(self.host.editor_state());
+        }
+
         if self.try_init_render_context(event_loop) {
             if let (Some(ctx), Some(backend)) = (self.ctx.as_mut(), self.backend.as_mut()) {
                 frame::paint(
diff --git a/crates/op-host-desktop/src/main_tests.rs b/crates/op-host-desktop/src/main_tests.rs
index 51fae21be..a9b8464d4 100644
--- a/crates/op-host-desktop/src/main_tests.rs
+++ b/crates/op-host-desktop/src/main_tests.rs
@@ -126,3 +126,33 @@ fn live_mcp_http_server_applies_write_requests_to_editor_state() {
         "MCP write should mutate the live editor state"
     );
 }
+
+#[test]
+fn startup_mcp_bootstrap_starts_live_server_for_enabled_cli() {
+    let mut app = DesktopApp::new(None);
+    let settings = &mut app.host.editor_state_mut().editor_ui.agent_settings;
+    settings.mcp_server.port = 0;
+    settings.mcp_server.running = false;
+    let codex_idx = op_editor_core::agent_settings::McpCli::ALL
+        .iter()
+        .position(|cli| *cli == op_editor_core::agent_settings::McpCli::Codex)
+        .expect("Codex CLI index");
+    settings.mcp_cli_enabled[codex_idx] = true;
+
+    assert!(app.bootstrap_mcp_runtime_from_settings());
+
+    assert!(app.mcp_server_active());
+    assert!(
+        app.host
+            .editor_state()
+            .editor_ui
+            .agent_settings
+            .mcp_server
+            .running
+    );
+    assert_ne!(
+        app.mcp_server.as_ref().expect("server").port(),
+        0,
+        "ephemeral port should be reported after binding"
+    );
+}
diff --git a/crates/op-host-desktop/src/mcp_integrations.rs b/crates/op-host-desktop/src/mcp_integrations.rs
index b01881649..87791a17b 100644
--- a/crates/op-host-desktop/src/mcp_integrations.rs
+++ b/crates/op-host-desktop/src/mcp_integrations.rs
@@ -18,6 +18,13 @@ pub(crate) fn set_cli_enabled(cli: McpCli, enabled: bool, port: u16) -> Result<P
     set_cli_enabled_at_path(cli, enabled, port, path)
 }
 
+pub(crate) fn detect_enabled_clis() -> [bool; 6] {
+    let Some(home) = dirs::home_dir() else {
+        return [false; 6];
+    };
+    detect_enabled_clis_for_home(&home, true)
+}
+
 #[cfg(test)]
 fn set_cli_enabled_at_home(
     cli: McpCli,
@@ -29,6 +36,20 @@ fn set_cli_enabled_at_home(
     set_cli_enabled_at_path(cli, enabled, port, path)
 }
 
+#[cfg(test)]
+fn detect_enabled_clis_at_home(home: &Path) -> [bool; 6] {
+    detect_enabled_clis_for_home(home, false)
+}
+
+fn detect_enabled_clis_for_home(home: &Path, use_env: bool) -> [bool; 6] {
+    let mut flags = [false; 6];
+    for (idx, cli) in McpCli::ALL.iter().copied().enumerate() {
+        let path = config_path(cli, home, use_env);
+        flags[idx] = cli_config_has_openpencil(cli, &path);
+    }
+    flags
+}
+
 fn set_cli_enabled_at_path(
     cli: McpCli,
     enabled: bool,
@@ -46,6 +67,19 @@ fn set_cli_enabled_at_path(
     Ok(path)
 }
 
+fn cli_config_has_openpencil(cli: McpCli, path: &Path) -> bool {
+    match cli {
+        McpCli::Codex => fs::read_to_string(path)
+            .map(|text| codex_config_has_openpencil(&text))
+            .unwrap_or(false),
+        McpCli::ClaudeCode
+        | McpCli::Gemini
+        | McpCli::OpenCode
+        | McpCli::Kiro
+        | McpCli::GithubCopilot => json_config_has_openpencil(path),
+    }
+}
+
 fn config_path(cli: McpCli, home: &Path, use_env: bool) -> PathBuf {
     match cli {
         McpCli::ClaudeCode => home.join(".claude.json"),
@@ -66,6 +100,17 @@ fn config_path(cli: McpCli, home: &Path, use_env: bool) -> PathBuf {
     }
 }
 
+fn json_config_has_openpencil(path: &Path) -> bool {
+    read_json_object(path)
+        .ok()
+        .and_then(|root| {
+            root.get("mcpServers")
+                .and_then(Value::as_object)
+                .map(|servers| servers.contains_key(SERVER_NAME))
+        })
+        .unwrap_or(false)
+}
+
 fn update_json_config(path: &Path, enabled: bool, port: u16) -> Result<(), String> {
     let mut root = read_json_object(path)?;
     if enabled {
@@ -145,6 +190,10 @@ fn update_codex_config(path: &Path, enabled: bool, port: u16) -> Result<(), Stri
     fs::write(path, text).map_err(|e| format!("write {}: {e}", path.display()))
 }
 
+fn codex_config_has_openpencil(input: &str) -> bool {
+    input.lines().map(str::trim).any(is_codex_openpencil_table)
+}
+
 fn remove_codex_server_block(input: &str) -> String {
     let mut out = String::new();
     let mut skipping = false;
@@ -255,4 +304,30 @@ mod tests {
 
         let _ = fs::remove_dir_all(home);
     }
+
+    #[test]
+    fn detects_legacy_codex_openpencil_server_config() {
+        let home = temp_home("codex-detect");
+        let path = home.join(".codex").join("config.toml");
+        fs::create_dir_all(path.parent().expect("parent")).expect("create codex dir");
+        fs::write(
+            &path,
+            "model = \"gpt-5\"\n\n[mcp_servers.openpencil]\ncommand = \"/usr/local/bin/node\"\nargs = [\"/Applications/OpenPencil.app/Contents/Resources/mcp-server.cjs\"]\n",
+        )
+        .expect("seed legacy config");
+
+        let flags = detect_enabled_clis_at_home(&home);
+
+        let codex_idx = McpCli::ALL
+            .iter()
+            .position(|cli| *cli == McpCli::Codex)
+            .expect("Codex CLI index");
+        assert!(flags[codex_idx]);
+        assert!(
+            flags.iter().filter(|enabled| **enabled).count() == 1,
+            "{flags:?}"
+        );
+
+        let _ = fs::remove_dir_all(home);
+    }
 }
diff --git a/crates/op-host-desktop/src/mcp_live.rs b/crates/op-host-desktop/src/mcp_live.rs
index 34e7e6aed..5bbe975bf 100644
--- a/crates/op-host-desktop/src/mcp_live.rs
+++ b/crates/op-host-desktop/src/mcp_live.rs
@@ -40,6 +40,10 @@ impl McpLiveServer {
     pub(crate) fn start(port: u16) -> Result<Self, String> {
         let listener = TcpListener::bind(("127.0.0.1", port))
             .map_err(|e| format!("bind 127.0.0.1:{port}: {e}"))?;
+        let bound_port = listener
+            .local_addr()
+            .map_err(|e| format!("read bound MCP port: {e}"))?
+            .port();
         listener
             .set_nonblocking(true)
             .map_err(|e| format!("set nonblocking: {e}"))?;
@@ -49,9 +53,9 @@ impl McpLiveServer {
             .name("op-mcp-live-http".into())
             .spawn(move || server_loop(listener, req_tx, stop_rx))
             .map_err(|e| format!("spawn MCP live server: {e}"))?;
-        eprintln!("openpencil-desktop mcp: listening on 127.0.0.1:{port}/mcp");
+        eprintln!("openpencil-desktop mcp: listening on 127.0.0.1:{bound_port}/mcp");
         Ok(Self {
-            port,
+            port: bound_port,
             req_rx,
             stop_tx,
         })
diff --git a/crates/op-host-desktop/src/mcp_runtime.rs b/crates/op-host-desktop/src/mcp_runtime.rs
index ea2546425..8fff34b7f 100644
--- a/crates/op-host-desktop/src/mcp_runtime.rs
+++ b/crates/op-host-desktop/src/mcp_runtime.rs
@@ -3,6 +3,35 @@
 use super::{mcp_integrations, mcp_live, DesktopApp};
 
 impl DesktopApp {
+    pub(crate) fn bootstrap_mcp_runtime_from_settings(&mut self) -> bool {
+        let detected_flags = mcp_integrations::detect_enabled_clis();
+        let settings = &mut self.host.editor_state_mut().editor_ui.agent_settings;
+        let mut changed = false;
+        for (idx, detected) in detected_flags.iter().copied().enumerate() {
+            if detected && !settings.mcp_cli_enabled[idx] {
+                settings.mcp_cli_enabled[idx] = true;
+                changed = true;
+            }
+        }
+        let any_cli_enabled = settings.mcp_cli_enabled.iter().any(|enabled| *enabled);
+        let port = settings.mcp_server.port;
+        if any_cli_enabled && !settings.mcp_server.running {
+            settings.mcp_server.running = true;
+            changed = true;
+        }
+        if changed {
+            self.host.mark_editor_state_dirty();
+        }
+        if any_cli_enabled && port != 0 {
+            changed |= self.reconcile_mcp_cli_integrations(Some(([false; 6], port)));
+        }
+        changed |= self.reconcile_mcp_server_from_settings();
+        if self.mcp_server_active() {
+            changed |= self.request_redraw(false);
+        }
+        changed
+    }
+
     pub(crate) fn reconcile_mcp_server_from_settings(&mut self) -> bool {
         let desired = self
             .host