diff --git a/doc/DOCKER.md b/doc/DOCKER.md
index 9cc867db..82559bf8 100644
--- a/doc/DOCKER.md
+++ b/doc/DOCKER.md
@@ -123,5 +123,6 @@ Notes:
 - Smoke script defaults to `authenticated/private` mode so `HOST=0.0.0.0` can be exposed to the host.
 - Smoke script defaults host port to `3131` to avoid conflicts with local Paperclip on `3100`.
 - Smoke script also defaults `PAPERCLIP_PUBLIC_URL` to `http://localhost:<HOST_PORT>` so bootstrap invite URLs and auth callbacks use the reachable host port instead of the container's internal `3100`.
+- In authenticated mode, the smoke script defaults `SMOKE_AUTO_BOOTSTRAP=true` and drives the real bootstrap path automatically: it signs up a real user, runs `paperclipai auth bootstrap-ceo` inside the container to mint a real bootstrap invite, accepts that invite over HTTP, and verifies board session access.
 - Run the script in the foreground to watch the onboarding flow; stop with `Ctrl+C` after validation.
 - The image definition is in `Dockerfile.onboard-smoke`.
diff --git a/scripts/docker-onboard-smoke.sh b/scripts/docker-onboard-smoke.sh
index 3b3e24d8..c441a623 100755
--- a/scripts/docker-onboard-smoke.sh
+++ b/scripts/docker-onboard-smoke.sh
@@ -10,14 +10,187 @@ HOST_UID="${HOST_UID:-$(id -u)}"
 PAPERCLIP_DEPLOYMENT_MODE="${PAPERCLIP_DEPLOYMENT_MODE:-authenticated}"
 PAPERCLIP_DEPLOYMENT_EXPOSURE="${PAPERCLIP_DEPLOYMENT_EXPOSURE:-private}"
 PAPERCLIP_PUBLIC_URL="${PAPERCLIP_PUBLIC_URL:-http://localhost:${HOST_PORT}}"
-DOCKER_TTY_ARGS=()
-
-if [[ -t 0 && -t 1 ]]; then
-  DOCKER_TTY_ARGS=(-it)
-fi
+SMOKE_AUTO_BOOTSTRAP="${SMOKE_AUTO_BOOTSTRAP:-true}"
+SMOKE_ADMIN_NAME="${SMOKE_ADMIN_NAME:-Smoke Admin}"
+SMOKE_ADMIN_EMAIL="${SMOKE_ADMIN_EMAIL:-smoke-admin@paperclip.local}"
+SMOKE_ADMIN_PASSWORD="${SMOKE_ADMIN_PASSWORD:-paperclip-smoke-password}"
+CONTAINER_NAME="${IMAGE_NAME//[^a-zA-Z0-9_.-]/-}"
+LOG_PID=""
+COOKIE_JAR=""
+TMP_DIR=""
 
 mkdir -p "$DATA_DIR"
 
+cleanup() {
+  if [[ -n "$LOG_PID" ]]; then
+    kill "$LOG_PID" >/dev/null 2>&1 || true
+  fi
+  docker stop "$CONTAINER_NAME" >/dev/null 2>&1 || true
+  if [[ -n "$TMP_DIR" && -d "$TMP_DIR" ]]; then
+    rm -rf "$TMP_DIR"
+  fi
+}
+
+trap cleanup EXIT INT TERM
+
+wait_for_http() {
+  local url="$1"
+  local attempts="${2:-60}"
+  local sleep_seconds="${3:-1}"
+  local i
+  for ((i = 1; i <= attempts; i += 1)); do
+    if curl -fsS "$url" >/dev/null 2>&1; then
+      return 0
+    fi
+    sleep "$sleep_seconds"
+  done
+  return 1
+}
+
+generate_bootstrap_invite_url() {
+  local bootstrap_output
+  bootstrap_output="$(
+    docker exec \
+      -e PAPERCLIP_DEPLOYMENT_MODE="$PAPERCLIP_DEPLOYMENT_MODE" \
+      -e PAPERCLIP_DEPLOYMENT_EXPOSURE="$PAPERCLIP_DEPLOYMENT_EXPOSURE" \
+      -e PAPERCLIP_PUBLIC_URL="$PAPERCLIP_PUBLIC_URL" \
+      -e PAPERCLIP_HOME="/paperclip" \
+      "$CONTAINER_NAME" bash -lc \
+      'npx --yes "paperclipai@${PAPERCLIPAI_VERSION}" auth bootstrap-ceo --data-dir "$PAPERCLIP_HOME" --base-url "$PAPERCLIP_PUBLIC_URL"' \
+      2>&1
+  )" || {
+    echo "Smoke bootstrap failed: could not run bootstrap-ceo inside container" >&2
+    printf '%s\n' "$bootstrap_output" >&2
+    return 1
+  }
+
+  local invite_url
+  invite_url="$(
+    printf '%s\n' "$bootstrap_output" \
+      | grep -o 'https\?://[^[:space:]]*/invite/pcp_bootstrap_[[:alnum:]]*' \
+      | tail -n 1
+  )"
+
+  if [[ -z "$invite_url" ]]; then
+    echo "Smoke bootstrap failed: bootstrap-ceo did not print an invite URL" >&2
+    printf '%s\n' "$bootstrap_output" >&2
+    return 1
+  fi
+
+  printf '%s\n' "$invite_url"
+}
+
+post_json_with_cookies() {
+  local url="$1"
+  local body="$2"
+  local output_file="$3"
+  curl -sS \
+    -o "$output_file" \
+    -w "%{http_code}" \
+    -c "$COOKIE_JAR" \
+    -b "$COOKIE_JAR" \
+    -H "Content-Type: application/json" \
+    -H "Origin: $PAPERCLIP_PUBLIC_URL" \
+    -X POST \
+    "$url" \
+    --data "$body"
+}
+
+get_with_cookies() {
+  local url="$1"
+  curl -fsS \
+    -c "$COOKIE_JAR" \
+    -b "$COOKIE_JAR" \
+    -H "Accept: application/json" \
+    "$url"
+}
+
+sign_up_or_sign_in() {
+  local signup_response="$TMP_DIR/signup.json"
+  local signup_status
+  signup_status="$(post_json_with_cookies \
+    "$PAPERCLIP_PUBLIC_URL/api/auth/sign-up/email" \
+    "{\"name\":\"$SMOKE_ADMIN_NAME\",\"email\":\"$SMOKE_ADMIN_EMAIL\",\"password\":\"$SMOKE_ADMIN_PASSWORD\"}" \
+    "$signup_response")"
+  if [[ "$signup_status" =~ ^2 ]]; then
+    echo "    Smoke bootstrap: created admin user $SMOKE_ADMIN_EMAIL"
+    return 0
+  fi
+
+  local signin_response="$TMP_DIR/signin.json"
+  local signin_status
+  signin_status="$(post_json_with_cookies \
+    "$PAPERCLIP_PUBLIC_URL/api/auth/sign-in/email" \
+    "{\"email\":\"$SMOKE_ADMIN_EMAIL\",\"password\":\"$SMOKE_ADMIN_PASSWORD\"}" \
+    "$signin_response")"
+  if [[ "$signin_status" =~ ^2 ]]; then
+    echo "    Smoke bootstrap: signed in existing admin user $SMOKE_ADMIN_EMAIL"
+    return 0
+  fi
+
+  echo "Smoke bootstrap failed: could not sign up or sign in admin user" >&2
+  echo "Sign-up response:" >&2
+  cat "$signup_response" >&2 || true
+  echo >&2
+  echo "Sign-in response:" >&2
+  cat "$signin_response" >&2 || true
+  echo >&2
+  return 1
+}
+
+auto_bootstrap_authenticated_smoke() {
+  local health_url="$PAPERCLIP_PUBLIC_URL/api/health"
+  local health_json
+  health_json="$(curl -fsS "$health_url")"
+  if [[ "$health_json" != *'"deploymentMode":"authenticated"'* ]]; then
+    return 0
+  fi
+
+  sign_up_or_sign_in
+
+  if [[ "$health_json" == *'"bootstrapStatus":"ready"'* ]]; then
+    echo "    Smoke bootstrap: instance already ready"
+  else
+    local invite_url
+    invite_url="$(generate_bootstrap_invite_url)"
+    echo "    Smoke bootstrap: generated bootstrap invite via auth bootstrap-ceo"
+
+    local invite_token="${invite_url##*/}"
+    local accept_response="$TMP_DIR/accept.json"
+    local accept_status
+    accept_status="$(post_json_with_cookies \
+      "$PAPERCLIP_PUBLIC_URL/api/invites/$invite_token/accept" \
+      '{"requestType":"human"}' \
+      "$accept_response")"
+    if [[ ! "$accept_status" =~ ^2 ]]; then
+      echo "Smoke bootstrap failed: bootstrap invite acceptance returned HTTP $accept_status" >&2
+      cat "$accept_response" >&2 || true
+      echo >&2
+      return 1
+    fi
+    echo "    Smoke bootstrap: accepted bootstrap invite"
+  fi
+
+  local session_json
+  session_json="$(get_with_cookies "$PAPERCLIP_PUBLIC_URL/api/auth/get-session")"
+  if [[ "$session_json" != *'"userId"'* ]]; then
+    echo "Smoke bootstrap failed: no authenticated session after bootstrap" >&2
+    echo "$session_json" >&2
+    return 1
+  fi
+
+  local companies_json
+  companies_json="$(get_with_cookies "$PAPERCLIP_PUBLIC_URL/api/companies")"
+  if [[ "${companies_json:0:1}" != "[" ]]; then
+    echo "Smoke bootstrap failed: board companies endpoint did not return JSON array" >&2
+    echo "$companies_json" >&2
+    return 1
+  fi
+
+  echo "    Smoke bootstrap: board session verified"
+  echo "    Smoke admin credentials: $SMOKE_ADMIN_EMAIL / $SMOKE_ADMIN_PASSWORD"
+}
+
 echo "==> Building onboard smoke image"
 docker build \
   --build-arg PAPERCLIPAI_VERSION="$PAPERCLIPAI_VERSION" \
@@ -29,12 +202,15 @@ docker build \
 echo "==> Running onboard smoke container"
 echo "    UI should be reachable at: http://localhost:$HOST_PORT"
 echo "    Public URL: $PAPERCLIP_PUBLIC_URL"
+echo "    Smoke auto-bootstrap: $SMOKE_AUTO_BOOTSTRAP"
 echo "    Data dir: $DATA_DIR"
 echo "    Deployment: $PAPERCLIP_DEPLOYMENT_MODE/$PAPERCLIP_DEPLOYMENT_EXPOSURE"
 echo "    Live output: onboard banner and server logs stream in this terminal (Ctrl+C to stop)"
-docker run --rm \
-  "${DOCKER_TTY_ARGS[@]}" \
-  --name "${IMAGE_NAME//[^a-zA-Z0-9_.-]/-}" \
+
+docker rm -f "$CONTAINER_NAME" >/dev/null 2>&1 || true
+
+docker run -d --rm \
+  --name "$CONTAINER_NAME" \
   -p "$HOST_PORT:3100" \
   -e HOST=0.0.0.0 \
   -e PORT=3100 \
@@ -42,4 +218,21 @@ docker run --rm \
   -e PAPERCLIP_DEPLOYMENT_EXPOSURE="$PAPERCLIP_DEPLOYMENT_EXPOSURE" \
   -e PAPERCLIP_PUBLIC_URL="$PAPERCLIP_PUBLIC_URL" \
   -v "$DATA_DIR:/paperclip" \
-  "$IMAGE_NAME"
+  "$IMAGE_NAME" >/dev/null
+
+docker logs -f "$CONTAINER_NAME" &
+LOG_PID=$!
+
+TMP_DIR="$(mktemp -d "${TMPDIR:-/tmp}/paperclip-onboard-smoke.XXXXXX")"
+COOKIE_JAR="$TMP_DIR/cookies.txt"
+
+if ! wait_for_http "$PAPERCLIP_PUBLIC_URL/api/health" 90 1; then
+  echo "Smoke bootstrap failed: server did not become ready at $PAPERCLIP_PUBLIC_URL/api/health" >&2
+  exit 1
+fi
+
+if [[ "$SMOKE_AUTO_BOOTSTRAP" == "true" && "$PAPERCLIP_DEPLOYMENT_MODE" == "authenticated" ]]; then
+  auto_bootstrap_authenticated_smoke
+fi
+
+wait "$LOG_PID"
diff --git a/server/src/routes/health.ts b/server/src/routes/health.ts
index 9a95f6e8..ddc7c441 100644
--- a/server/src/routes/health.ts
+++ b/server/src/routes/health.ts
@@ -1,7 +1,7 @@
 import { Router } from "express";
 import type { Db } from "@paperclipai/db";
-import { count, sql } from "drizzle-orm";
-import { instanceUserRoles } from "@paperclipai/db";
+import { and, count, eq, gt, isNull, sql } from "drizzle-orm";
+import { instanceUserRoles, invites } from "@paperclipai/db";
 import type { DeploymentExposure, DeploymentMode } from "@paperclipai/shared";
 
 export function healthRoutes(
@@ -27,6 +27,7 @@ export function healthRoutes(
     }
 
     let bootstrapStatus: "ready" | "bootstrap_pending" = "ready";
+    let bootstrapInviteActive = false;
     if (opts.deploymentMode === "authenticated") {
       const roleCount = await db
         .select({ count: count() })
@@ -34,6 +35,23 @@ export function healthRoutes(
         .where(sql`${instanceUserRoles.role} = 'instance_admin'`)
         .then((rows) => Number(rows[0]?.count ?? 0));
       bootstrapStatus = roleCount > 0 ? "ready" : "bootstrap_pending";
+
+      if (bootstrapStatus === "bootstrap_pending") {
+        const now = new Date();
+        const inviteCount = await db
+          .select({ count: count() })
+          .from(invites)
+          .where(
+            and(
+              eq(invites.inviteType, "bootstrap_ceo"),
+              isNull(invites.revokedAt),
+              isNull(invites.acceptedAt),
+              gt(invites.expiresAt, now),
+            ),
+          )
+          .then((rows) => Number(rows[0]?.count ?? 0));
+        bootstrapInviteActive = inviteCount > 0;
+      }
     }
 
     res.json({
@@ -42,6 +60,7 @@ export function healthRoutes(
       deploymentExposure: opts.deploymentExposure,
       authReady: opts.authReady,
       bootstrapStatus,
+      bootstrapInviteActive,
       features: {
         companyDeletionEnabled: opts.companyDeletionEnabled,
       },
diff --git a/ui/src/App.tsx b/ui/src/App.tsx
index 18df83d8..ee6db712 100644
--- a/ui/src/App.tsx
+++ b/ui/src/App.tsx
@@ -32,14 +32,15 @@ import { queryKeys } from "./lib/queryKeys";
 import { useCompany } from "./context/CompanyContext";
 import { useDialog } from "./context/DialogContext";
 
-function BootstrapPendingPage() {
+function BootstrapPendingPage({ hasActiveInvite = false }: { hasActiveInvite?: boolean }) {
   return (
     <div className="mx-auto max-w-xl py-10">
       <div className="rounded-lg border border-border bg-card p-6">
         <h1 className="text-xl font-semibold">Instance setup required</h1>
         <p className="mt-2 text-sm text-muted-foreground">
-          No instance admin exists yet. Run this command in your Paperclip environment to generate
-          the first admin invite URL:
+          {hasActiveInvite
+            ? "No instance admin exists yet. A bootstrap invite is already active. Check your Paperclip startup logs for the first admin invite URL, or run this command to rotate it:"
+            : "No instance admin exists yet. Run this command in your Paperclip environment to generate the first admin invite URL:"}
         </p>
         <pre className="mt-4 overflow-x-auto rounded-md border border-border bg-muted/30 p-3 text-xs">
 {`pnpm paperclipai auth bootstrap-ceo`}
@@ -78,7 +79,7 @@ function CloudAccessGate() {
   }
 
   if (isAuthenticatedMode && healthQuery.data?.bootstrapStatus === "bootstrap_pending") {
-    return <BootstrapPendingPage />;
+    return <BootstrapPendingPage hasActiveInvite={healthQuery.data.bootstrapInviteActive} />;
   }
 
   if (isAuthenticatedMode && !sessionQuery.data) {
diff --git a/ui/src/api/health.ts b/ui/src/api/health.ts
index 614bb522..cb1b1374 100644
--- a/ui/src/api/health.ts
+++ b/ui/src/api/health.ts
@@ -4,6 +4,7 @@ export type HealthStatus = {
   deploymentExposure?: "private" | "public";
   authReady?: boolean;
   bootstrapStatus?: "ready" | "bootstrap_pending";
+  bootstrapInviteActive?: boolean;
   features?: {
     companyDeletionEnabled?: boolean;
   };