diff --git a/PiMobile/APIClient.swift b/PiMobile/APIClient.swift
index d8e9f78..c2d3ab3 100644
--- a/PiMobile/APIClient.swift
+++ b/PiMobile/APIClient.swift
@@ -181,10 +181,17 @@ final class APIClient {
         return try decoder.decode(T.self, from: data)
     }
 
-    private func post(_ path: String, body: some Encodable) async throws -> Data {
-        guard let mac = activeMac, let url = URL(string: mac.baseURL + path) else { throw APIError.badURL }
+    private func post(
+        _ path: String,
+        on requestedMac: MacServer? = nil,
+        body: some Encodable,
+        timeoutInterval: TimeInterval = 60
+    ) async throws -> Data {
+        guard let mac = requestedMac ?? activeMac,
+              let url = URL(string: mac.baseURL + path) else { throw APIError.badURL }
         var request = URLRequest(url: url)
         request.httpMethod = "POST"
+        request.timeoutInterval = timeoutInterval
         request.setValue("Bearer \(mac.token)", forHTTPHeaderField: "Authorization")
         request.setValue("application/json", forHTTPHeaderField: "Content-Type")
         // Request bodies stay camelCase to match the companion server's JSON.
@@ -206,6 +213,15 @@ final class APIClient {
 
     func repos(on mac: MacServer) async throws -> [Repo] { try await get("/repos", on: mac) }
     func piVersion(on mac: MacServer) async throws -> PiVersionInfo { try await get("/pi-version", on: mac) }
+    func updatePi(on mac: MacServer) async throws -> PiVersionInfo {
+        let data = try await post(
+            "/pi-update",
+            on: mac,
+            body: [String: String](),
+            timeoutInterval: 180
+        )
+        return try decoder.decode(PiVersionInfo.self, from: data)
+    }
 
     func loadModelGroups() async {
         // Keep the last good list on failure (older server without /models, offline).
diff --git a/PiMobile/Views/SettingsView.swift b/PiMobile/Views/SettingsView.swift
index d575c39..a51d16d 100644
--- a/PiMobile/Views/SettingsView.swift
+++ b/PiMobile/Views/SettingsView.swift
@@ -5,6 +5,8 @@ struct SettingsView: View {
     @Environment(\.dismiss) private var dismiss
     @State private var statuses: [UUID: Bool] = [:]
     @State private var piVersions: [UUID: PiVersionInfo] = [:]
+    @State private var piUpdatesInFlight: Set<UUID> = []
+    @State private var piUpdateErrors: [UUID: String] = [:]
 
     private var macsNeedingPiUpdate: [(mac: MacServer, info: PiVersionInfo)] {
         api.macs.compactMap { mac in
@@ -22,28 +24,44 @@ struct SettingsView: View {
                             VStack(alignment: .leading, spacing: 10) {
                                 Text("\(item.mac.name) is on Pi \(item.info.current ?? "?"); \(item.info.latest ?? "?") is available.")
                                     .font(.subheadline)
-                                HStack {
-                                    Text(item.info.updateCommand)
-                                        .font(.caption.monospaced())
-                                        .foregroundStyle(Theme.accent)
-                                        .textSelection(.enabled)
-                                    Spacer()
-                                    Button {
-                                        UIPasteboard.general.string = item.info.updateCommand
-                                    } label: {
-                                        Image(systemName: "doc.on.doc")
+                                Button {
+                                    Task { await updatePi(on: item.mac) }
+                                } label: {
+                                    HStack(spacing: 8) {
+                                        if piUpdatesInFlight.contains(item.mac.id) {
+                                            ProgressView()
+                                                .controlSize(.small)
+                                            Text("Updating…")
+                                        } else {
+                                            Label(
+                                                piUpdateErrors[item.mac.id] == nil ? "Update Pi" : "Try Again",
+                                                systemImage: "arrow.down.circle"
+                                            )
+                                        }
                                     }
-                                    .buttonStyle(.borderless)
+                                    .frame(maxWidth: .infinity)
+                                }
+                                .buttonStyle(.borderedProminent)
+                                .disabled(piUpdatesInFlight.contains(item.mac.id))
+                                .accessibilityLabel(
+                                    piUpdatesInFlight.contains(item.mac.id)
+                                        ? "Updating Pi on \(item.mac.name)"
+                                        : "Update Pi on \(item.mac.name)"
+                                )
+
+                                if let error = piUpdateErrors[item.mac.id] {
+                                    Label(error, systemImage: "exclamationmark.triangle.fill")
+                                        .font(.caption)
+                                        .foregroundStyle(.red)
+                                        .accessibilityLabel("Pi update failed: \(error)")
                                 }
-                                .padding(10)
-                                .background(Theme.accent.opacity(0.08), in: RoundedRectangle(cornerRadius: 8))
                             }
                             .padding(.vertical, 2)
                         }
                     } header: {
                         Text("Update Pi")
                     } footer: {
-                        Text("Run this in Terminal on that Mac — Pi updates there, not in this app.")
+                        Text("Pi Companion updates Pi directly on that Mac. Finish any running Pi turn first.")
                     }
                 }
 
@@ -172,6 +190,21 @@ struct SettingsView: View {
             }
         }
     }
+
+    private func updatePi(on mac: MacServer) async {
+        piUpdateErrors[mac.id] = nil
+        piUpdatesInFlight.insert(mac.id)
+        defer { piUpdatesInFlight.remove(mac.id) }
+
+        do {
+            let info = try await api.updatePi(on: mac)
+            withAnimation(.easeOut(duration: 0.2)) {
+                piVersions[mac.id] = info
+            }
+        } catch {
+            piUpdateErrors[mac.id] = error.localizedDescription
+        }
+    }
 }
 
 struct MacEditView: View {
diff --git a/server/install.sh b/server/install.sh
index 887d06b..7452b7e 100755
--- a/server/install.sh
+++ b/server/install.sh
@@ -13,7 +13,7 @@ AGENT_PATH="$HOME/.local/bin:$HOME/.bun/bin:/opt/homebrew/bin:/usr/local/bin:/us
 # Refuse to run from inside the companion service itself (e.g. a Pi agent turn
 # spawned by the server): bootout would kill this script's own process tree
 # mid-install, leaving the service unloaded and the turn dead.
-SVC_PID="$(launchctl print "gui/$(id -u)/$LABEL" 2>/dev/null | awk '/pid =/{print $3; exit}')"
+SVC_PID="$(launchctl print "gui/$(id -u)/$LABEL" 2>/dev/null | awk '/pid =/{print $3; exit}' || true)"
 p=$$
 while [[ -n "${SVC_PID:-}" && "$p" -gt 1 ]]; do
   if [[ "$p" == "$SVC_PID" ]]; then
diff --git a/server/server.ts b/server/server.ts
index ece0010..da7209d 100644
--- a/server/server.ts
+++ b/server/server.ts
@@ -10,7 +10,7 @@ const SESSIONS_ROOT = `${homedir()}/.pi/agent/sessions`;
 const PORT = Number(process.env.PORT ?? 8940);
 // LaunchAgents get a tiny PATH — resolve `pi` explicitly so model listing and
 // RPC turns work even when ~/.local/bin isn't on it.
-const PI = [
+const PI = process.env.PI_PATH ?? [
   `${homedir()}/.local/bin/pi`,
   "/opt/homebrew/bin/pi",
   "/usr/local/bin/pi",
@@ -620,7 +620,7 @@ function isOlder(current: string, latest: string): boolean {
 }
 
 async function refreshPiVersion() {
-  const p = Bun.spawnSync(["pi", "--version"], { stdout: "pipe", stderr: "pipe" });
+  const p = Bun.spawnSync([PI, "--version"], { stdout: "pipe", stderr: "pipe", env: piEnv() });
   const raw = p.exitCode === 0
     ? (p.stdout.toString().trim() || p.stderr.toString().trim())
     : "";
@@ -717,12 +717,58 @@ type Turn = {
   pendingUI: PendingUI | null;
 };
 const turns = new Map<string, Turn>();
+let piUpdateInProgress = false;
+
+type PiUpdateError = { error: string; status: number };
+
+async function updatePiInstall(): Promise<PiVersionInfo | PiUpdateError> {
+  if (piUpdateInProgress) return { error: "Pi is already updating", status: 409 };
+  if ([...turns.values()].some((turn) => turn.running))
+    return { error: "Wait for active Pi turns to finish before updating", status: 409 };
+
+  piUpdateInProgress = true;
+  try {
+    const proc = Bun.spawn([PI, "update", "--self", "--no-approve"], {
+      cwd: homedir(),
+      stdout: "pipe",
+      stderr: "pipe",
+      env: piEnv(),
+    });
+    const [stdout, stderr, exitCode] = await Promise.all([
+      new Response(proc.stdout as any).text(),
+      new Response(proc.stderr as any).text(),
+      proc.exited,
+    ]);
+    if (exitCode !== 0) {
+      const detail = (stderr.trim() || stdout.trim() || `pi update exited with status ${exitCode}`)
+        .replace(/\x1b\[[0-9;]*m/g, "")
+        .slice(0, 2000);
+      return { error: detail, status: 500 };
+    }
+
+    await refreshPiVersion();
+    if (!piVersionCache.current)
+      return { error: "Pi updated, but its installed version could not be verified", status: 500 };
+    if (piVersionCache.update_available)
+      return {
+        error: `Pi update finished, but ${piVersionCache.current} is still installed`,
+        status: 500,
+      };
+    await Promise.all([refreshModels(), refreshSkills()]);
+    return piVersionCache;
+  } catch (error) {
+    return { error: `Failed to update Pi: ${String(error)}`, status: 500 };
+  } finally {
+    piUpdateInProgress = false;
+  }
+}
 
 function sendMessage(
   sessionId: string,
   text: string,
   opts: { model?: string; thinking?: string; approvalMode?: string; images?: PromptImage[] } = {},
 ) {
+  if (piUpdateInProgress) return { error: "Pi is updating; try again when it finishes", status: 409 };
   const existing = turns.get(sessionId);
   if (existing?.running) return { error: "agent is already working", status: 409 };
 
@@ -930,6 +976,12 @@ Bun.serve({
     const path = new URL(req.url).pathname;
     let m: RegExpMatchArray | null;
     try {
+      if (req.method === "POST" && path === "/pi-update") {
+        const result = await updatePiInstall();
+        return "error" in result
+          ? Response.json({ error: result.error }, { status: result.status })
+          : Response.json(result);
+      }
       if (req.method === "POST" && (m = path.match(/^\/sessions\/([^/]+)\/send$/))) {
         const { text, model, thinking, approvalMode, images } = await req.json();
         const hasImages = Array.isArray(images) && images.length > 0;