diff --git a/cli/launcher/firstrun_darwin.go b/cli/launcher/firstrun_darwin.go
index dcb41e8..a3eab1d 100644
--- a/cli/launcher/firstrun_darwin.go
+++ b/cli/launcher/firstrun_darwin.go
@@ -40,11 +40,13 @@ const bootstrapServerName = "local"
 // configuration this app should quietly repair; it is an installation that
 // needs setting up again, and saying so is the whole point.
 //
-// Not covered: a database file that exists but holds no users — a truncated or
-// hand-emptied one. Answering that needs to open SQLite, which would drag the
-// driver into the launcher for a case far rarer than "I deleted my data
-// directory". The server refuses to start in that state and says why in
-// ~/.cix/logs/cix-server.err.
+// Not covered here: a database file that exists but holds no users. That case
+// is not rare at all — it is what a deleted data directory turns into on the
+// very next start, because the server creates the file and runs migrations
+// BEFORE it checks for an admin account, then refuses. Answering it from here
+// would need the SQLite driver in the launcher; instead the refusal itself is
+// recognised after the fact — see isBootstrapRefusal, and the Start handler
+// that routes it back to setup.
 func needsFirstRun() bool {
 	path, err := serverEnvPath()
 	if err != nil {
@@ -73,6 +75,23 @@ func needsFirstRun() bool {
 	return false
 }
 
+// isBootstrapRefusal recognises the server's no-admin-account refusal in a log
+// tail.
+//
+// This closes the gap needsFirstRun leaves open. Delete ~/.cix/data and the
+// first start attempt — a login-time autostart as easily as a click — recreates
+// an empty cix.db before bootstrapAuth refuses, so from then on the file exists
+// and needsFirstRun answers false. The one thing that still knows the database
+// has no accounts is the server itself, and it says so in words this matches:
+// "incomplete bootstrap configuration" (an email left in server.env after the
+// password was retired) and "no users in database" (neither var set). Both mean
+// exactly one thing — there is no admin account and the server will not invent
+// one — and for both, running setup again is the fix.
+func isBootstrapRefusal(logTail string) bool {
+	return strings.Contains(logTail, "incomplete bootstrap configuration") ||
+		strings.Contains(logTail, "no users in database")
+}
+
 // retireBootstrapPassword drops CIX_BOOTSTRAP_ADMIN_PASSWORD from server.env
 // once there is a running server, and therefore an account, that no longer
 // needs it.
@@ -118,7 +137,14 @@ func runFirstRun(u *updater) error {
 		"It is the login for the cix dashboard on this Mac — nothing is sent anywhere. " +
 		"A password is generated for you, and setup then downloads the server (about 40 MB)."
 
-	email, err := prompt("Set up cix", intro, "")
+	// On a re-run the previous admin's address is still in server.env, and the
+	// most likely answer is the same one — so offer it, editable.
+	priorEmail := ""
+	if prior, err := readServerEnv(); err == nil {
+		priorEmail = strings.TrimSpace(prior["CIX_BOOTSTRAP_ADMIN_EMAIL"])
+	}
+
+	email, err := prompt("Set up cix", intro, priorEmail)
 	if err != nil {
 		return err
 	}
diff --git a/cli/launcher/firstrun_darwin_test.go b/cli/launcher/firstrun_darwin_test.go
index 0caa5c9..4be7ded 100644
--- a/cli/launcher/firstrun_darwin_test.go
+++ b/cli/launcher/firstrun_darwin_test.go
@@ -91,6 +91,36 @@ func TestNeedsFirstRun(t *testing.T) {
 	})
 }
 
+// The two refusals bootstrapAuth emits on a user-less database must route to
+// setup, and other startup failures must not — a port clash is not a reason to
+// offer wiping anyone's configuration. The strings are copied from
+// server/cmd/cix-server/bootstrap.go; if the server rewords them, this test is
+// the tripwire.
+func TestIsBootstrapRefusal(t *testing.T) {
+	refusals := []string{
+		"cix-server: bootstrap auth: incomplete bootstrap configuration: " +
+			"CIX_BOOTSTRAP_ADMIN_EMAIL is set but CIX_BOOTSTRAP_ADMIN_PASSWORD is empty.",
+		"cix-server: bootstrap auth: no users in database and the bootstrap admin " +
+			"env vars are not set: refuse to start.",
+	}
+	for _, tail := range refusals {
+		if !isBootstrapRefusal(tail) {
+			t.Errorf("isBootstrapRefusal(%q) = false, want true", tail)
+		}
+	}
+
+	others := []string{
+		"listen tcp 127.0.0.1:21847: bind: address already in use",
+		"open database: unable to open database file",
+		"", // no log at all
+	}
+	for _, tail := range others {
+		if isBootstrapRefusal(tail) {
+			t.Errorf("isBootstrapRefusal(%q) = true, want false", tail)
+		}
+	}
+}
+
 func TestRetireBootstrapPassword(t *testing.T) {
 	home := t.TempDir()
 	t.Setenv("HOME", home)
diff --git a/cli/launcher/menu_darwin.go b/cli/launcher/menu_darwin.go
index cb3deed..da82bc9 100644
--- a/cli/launcher/menu_darwin.go
+++ b/cli/launcher/menu_darwin.go
@@ -460,19 +460,11 @@ func (m *menu) toggleServer() {
 	// log nobody has open, so the button appears to do nothing at all. Offer
 	// the thing that would actually help.
 	if needsFirstRun() {
-		ok, err := confirm("Set cix up again?",
-			"There is no cix database. If you deleted it, the server cannot start until an "+
-				"administrator account is created again.\n\n"+
-				"Setting up again creates a new account and a new, empty index. Anything that "+
-				"was indexed before is already gone with the database.",
-			"Set Up")
-		if err != nil || !ok {
-			return
-		}
-		if err := runFirstRun(m.updater); err != nil && !errors.Is(err, errCancelled) {
-			logf("re-running setup failed: %v", err)
-			_ = alert("Setup failed", fmt.Sprintf("cix could not set itself up again.\n\n%v", err))
-		}
+		m.offerSetupAgain(
+			"There is no cix database. If you deleted it, the server cannot start until an " +
+				"administrator account is created again.\n\n" +
+				"Setting up again creates a new account and a new, empty index. Anything that " +
+				"was indexed before is already gone with the database.")
 		m.poll.refresh()
 		return
 	}
@@ -494,12 +486,42 @@ func (m *menu) toggleServer() {
 	// a deleted database looked like a broken Start button.
 	if detail := serverDiedOnStart(); detail != "" {
 		logf("the server exited immediately after Start: %s", detail)
+		// One refusal deserves better than its log text: no admin account. The
+		// needsFirstRun check above cannot see this case, because the failed
+		// start itself recreated an empty cix.db — the file exists, the
+		// accounts do not. The server's own words are the reliable signal, so
+		// route them to setup instead of printing them.
+		if isBootstrapRefusal(detail) {
+			m.offerSetupAgain(
+				"The cix database exists but has no accounts — this is what deleting the data " +
+					"directory looks like after a start attempt recreates an empty database.\n\n" +
+					"The server will not start until an administrator account is created again. " +
+					"Setting up again creates a new account and a new, empty index.")
+			m.poll.refresh()
+			return
+		}
 		_ = alert("The server stopped straight away", detail+
 			"\n\nThe full log is in ~/.cix/logs/cix-server.err.")
 	}
 	m.poll.refresh()
 }
 
+// offerSetupAgain proposes re-running the setup wizard and runs it on consent.
+//
+// Shared by the two ways a gutted installation shows itself: the database file
+// is missing outright (needsFirstRun), or it exists, freshly recreated and
+// empty, and the server refused to start against it (isBootstrapRefusal).
+func (m *menu) offerSetupAgain(message string) {
+	ok, err := confirm("Set cix up again?", message, "Set Up")
+	if err != nil || !ok {
+		return
+	}
+	if err := runFirstRun(m.updater); err != nil && !errors.Is(err, errCancelled) {
+		logf("re-running setup failed: %v", err)
+		_ = alert("Setup failed", fmt.Sprintf("cix could not set itself up again.\n\n%v", err))
+	}
+}
+
 // toggleNetworkAccess switches CIX_BIND_ADDR between loopback and all
 // interfaces, then restarts the server so the change takes effect.
 //