diff --git a/go.mod b/go.mod
index 2485c3b5..bf3e2bda 100644
--- a/go.mod
+++ b/go.mod
@@ -7,7 +7,7 @@ require (
 	charm.land/bubbletea/v2 v2.0.8
 	charm.land/lipgloss/v2 v2.0.5
 	github.com/basecamp/basecamp-sdk/go v0.9.1-0.20260727173625-bb363c847b92
-	github.com/basecamp/cli v0.2.1
+	github.com/basecamp/cli v0.2.2-0.20260728023309-04e401b12c6c
 	github.com/charmbracelet/bubbles v1.0.0
 	github.com/charmbracelet/glamour v1.0.0
 	github.com/charmbracelet/huh v1.0.0
diff --git a/go.sum b/go.sum
index 68a29485..11a120dd 100644
--- a/go.sum
+++ b/go.sum
@@ -25,8 +25,8 @@ github.com/aymerick/douceur v0.2.0 h1:Mv+mAeH1Q+n9Fr+oyamOlAkUNPWPlA8PPGR0QAaYuP
 github.com/aymerick/douceur v0.2.0/go.mod h1:wlT5vV2O3h55X9m7iVYN0TBM0NH/MmbLnd30/FjWUq4=
 github.com/basecamp/basecamp-sdk/go v0.9.1-0.20260727173625-bb363c847b92 h1:4gQJTR8e5kBvXHDHLvef+Q00XY7KzWTxnQSLWMSPcyA=
 github.com/basecamp/basecamp-sdk/go v0.9.1-0.20260727173625-bb363c847b92/go.mod h1:r83ralDQ0q9vbAby5qQ5x9hgCgUdJLDLHYpiU6jaFjE=
-github.com/basecamp/cli v0.2.1 h1:8GyehPVtsTXla0oOPu4QgXRjwwzJ99prlByvyi+0HRQ=
-github.com/basecamp/cli v0.2.1/go.mod h1:p8tt/DatJ2LAzWO6N6tNfV8x3gF5T3IxDTo+U8FfWPo=
+github.com/basecamp/cli v0.2.2-0.20260728023309-04e401b12c6c h1:+5sQBl8sqYoD1Qhwsibn8sBCKWPyZ9NDez6mnuo9Afo=
+github.com/basecamp/cli v0.2.2-0.20260728023309-04e401b12c6c/go.mod h1:EK1Dba6DEw8ZAilVBpf/jri3ONDV7LQkLACSDe73f/c=
 github.com/bmatcuk/doublestar v1.1.1/go.mod h1:UD6OnuiIn0yFxxA2le/rnRU1G4RaI4UvFv1sNto9p6w=
 github.com/catppuccin/go v0.3.0 h1:d+0/YicIq+hSTo5oPuRi5kOpqkVA5tAsU6dNhvRu+aY=
 github.com/catppuccin/go v0.3.0/go.mod h1:8IHJuMGaUUjQM82qBrGNBv7LFq6JI3NnQCF6MOlZjpc=
diff --git a/internal/auth/keyring.go b/internal/auth/keyring.go
index 6fcc52a4..208482e5 100644
--- a/internal/auth/keyring.go
+++ b/internal/auth/keyring.go
@@ -5,8 +5,10 @@ import (
 	"fmt"
 	"os"
 	"sync"
+	"time"
 
 	"github.com/basecamp/cli/credstore"
+	"github.com/charmbracelet/x/term"
 )
 
 // Credentials holds OAuth tokens and metadata.
@@ -38,6 +40,30 @@ type Store struct {
 // newCredStore is replaceable in tests to avoid real keyring access.
 var newCredStore = credstore.NewStore
 
+// sessionIsHeadless reports that no human can answer a keyring unlock
+// prompt: stdin, stdout, and stderr are all non-terminals AND no GUI
+// session is available. Any attached stream counts as interactive —
+// redirecting a stream or two (`2>auth.log`, `| jq`) is routine interactive
+// use — and a GUI session (an app or IDE task runner launching the CLI with
+// all streams detached) can still present the unlock dialog. Replaceable in
+// tests.
+var sessionIsHeadless = func() bool {
+	return !term.IsTerminal(os.Stdin.Fd()) &&
+		!term.IsTerminal(os.Stdout.Fd()) &&
+		!term.IsTerminal(os.Stderr.Fd()) &&
+		!guiSessionAvailable()
+}
+
+// headlessProbeTimeout bounds the keyring availability probe when no
+// terminal is attached to any standard stream. A headless session (CI,
+// piped installers, ssh without a TTY) can never answer a keychain unlock
+// prompt, so an unavailable keyring must fall back to file storage instead
+// of hanging forever in an uncancellable `security` child — the #568
+// incident class. Interactive sessions keep the unbounded probe: a locked
+// keychain there raises an unlock prompt, and cutting it off mid-answer
+// would silently degrade the user to plaintext file storage.
+const headlessProbeTimeout = 10 * time.Second
+
 // NewStore creates a credential store. The OS keyring is not touched until
 // the first credential operation.
 func NewStore(fallbackDir string) *Store {
@@ -49,11 +75,15 @@ func NewStore(fallbackDir string) *Store {
 // sync.Once provides the synchronization.
 func (s *Store) ensure() *credstore.Store {
 	s.initOnce.Do(func() {
-		s.inner = newCredStore(credstore.StoreOptions{
+		opts := credstore.StoreOptions{
 			ServiceName:   "basecamp",
 			DisableEnvVar: "BASECAMP_NO_KEYRING",
 			FallbackDir:   s.fallbackDir,
-		})
+		}
+		if sessionIsHeadless() {
+			opts.ProbeTimeout = headlessProbeTimeout
+		}
+		s.inner = newCredStore(opts)
 	})
 	return s.inner
 }
diff --git a/internal/auth/keyring_test.go b/internal/auth/keyring_test.go
index 08a08f26..22b6701c 100644
--- a/internal/auth/keyring_test.go
+++ b/internal/auth/keyring_test.go
@@ -44,3 +44,37 @@ func TestNewStoreIsLazy(t *testing.T) {
 	store.UsingKeyring()
 	assert.Equal(t, 1, calls, "construction happens once")
 }
+
+// swapSessionIsHeadless replaces the interactivity seam for the test.
+func swapSessionIsHeadless(t *testing.T, headless bool) {
+	t.Helper()
+	orig := sessionIsHeadless
+	sessionIsHeadless = func() bool { return headless }
+	t.Cleanup(func() { sessionIsHeadless = orig })
+}
+
+// ensureOptions constructs a store's credstore through the seams and returns
+// the options it was built with.
+func ensureOptions(t *testing.T, headless bool) credstore.StoreOptions {
+	t.Helper()
+	t.Setenv("BASECAMP_NO_KEYRING", "1") // keep the delegated construction off the real keyring
+
+	var got credstore.StoreOptions
+	swapNewCredStore(t, func(opts credstore.StoreOptions) *credstore.Store {
+		got = opts
+		return credstore.NewStore(opts)
+	})
+	swapSessionIsHeadless(t, headless)
+
+	NewStore(t.TempDir()).UsingKeyring()
+	return got
+}
+
+// Headless sessions can never answer a keychain unlock prompt, so the probe
+// must be bounded there — the #568 incident class. Interactive sessions keep
+// the unbounded probe so a legitimate unlock prompt is never cut off
+// mid-answer (which would silently degrade to plaintext file storage).
+func TestEnsureBoundsProbeOnlyWhenHeadless(t *testing.T) {
+	assert.Equal(t, headlessProbeTimeout, ensureOptions(t, true).ProbeTimeout)
+	assert.Zero(t, ensureOptions(t, false).ProbeTimeout)
+}
diff --git a/internal/auth/session_darwin.go b/internal/auth/session_darwin.go
new file mode 100644
index 00000000..0fe2e206
--- /dev/null
+++ b/internal/auth/session_darwin.go
@@ -0,0 +1,23 @@
+package auth
+
+import (
+	"context"
+	"os/exec"
+	"strings"
+	"time"
+)
+
+// guiSessionAvailable reports whether the process runs inside a macOS Aqua
+// (GUI) session, where the keychain unlock prompt appears as a WindowServer
+// dialog even with every standard stream detached — GUI-launched apps and
+// IDE task runners. `launchctl managername` prints "Aqua" there; ssh and CI
+// run under StandardIO or Background. launchctl only inspects the launchd
+// session — it cannot touch the keychain — but is bounded anyway, and any
+// failure counts as no GUI so genuinely headless sessions keep the bounded
+// probe.
+func guiSessionAvailable() bool {
+	ctx, cancel := context.WithTimeout(context.Background(), 2*time.Second)
+	defer cancel()
+	out, err := exec.CommandContext(ctx, "/bin/launchctl", "managername").Output()
+	return err == nil && strings.TrimSpace(string(out)) == "Aqua"
+}
diff --git a/internal/auth/session_other.go b/internal/auth/session_other.go
new file mode 100644
index 00000000..ddbd20b9
--- /dev/null
+++ b/internal/auth/session_other.go
@@ -0,0 +1,11 @@
+//go:build !darwin && !windows
+
+package auth
+
+import "os"
+
+// guiSessionAvailable reports a display server the keyring's unlock prompt
+// could use even with every standard stream detached.
+func guiSessionAvailable() bool {
+	return os.Getenv("DISPLAY") != "" || os.Getenv("WAYLAND_DISPLAY") != ""
+}
diff --git a/internal/auth/session_other_test.go b/internal/auth/session_other_test.go
new file mode 100644
index 00000000..9e61c6ce
--- /dev/null
+++ b/internal/auth/session_other_test.go
@@ -0,0 +1,22 @@
+//go:build !darwin && !windows
+
+package auth
+
+import (
+	"testing"
+
+	"github.com/stretchr/testify/assert"
+)
+
+func TestGUISessionAvailableTracksDisplayEnv(t *testing.T) {
+	t.Setenv("DISPLAY", "")
+	t.Setenv("WAYLAND_DISPLAY", "")
+	assert.False(t, guiSessionAvailable())
+
+	t.Setenv("DISPLAY", ":0")
+	assert.True(t, guiSessionAvailable())
+
+	t.Setenv("DISPLAY", "")
+	t.Setenv("WAYLAND_DISPLAY", "wayland-0")
+	assert.True(t, guiSessionAvailable(), "Wayland-only sessions have no DISPLAY")
+}
diff --git a/internal/auth/session_windows.go b/internal/auth/session_windows.go
new file mode 100644
index 00000000..0e41782e
--- /dev/null
+++ b/internal/auth/session_windows.go
@@ -0,0 +1,9 @@
+package auth
+
+// guiSessionAvailable is always false on Windows: Credential Manager
+// operates without prompting, so a bounded probe cannot cut off an
+// interaction, and misclassifying a GUI-launched session as headless is
+// harmless here.
+func guiSessionAvailable() bool {
+	return false
+}