diff --git a/crates/tui/src/tui/backtrack.rs b/crates/tui/src/tui/backtrack.rs
new file mode 100644
index 00000000..0bf9e60b
--- /dev/null
+++ b/crates/tui/src/tui/backtrack.rs
@@ -0,0 +1,386 @@
+//! Esc-Esc backtrack state machine (issue #133).
+//!
+//! Lets the user rewind the active conversation to a previous user message.
+//! The chord is intentionally two-step so a single stray `Esc` after a popup
+//! close cannot accidentally rewind a turn:
+//!
+//! 1. **First Esc** (no popup, no streaming, nothing to clear) — moves
+//!    `Inactive` → `Primed`. The composer surfaces a transient hint
+//!    ("Press Esc again to backtrack"). A second Esc within the prime
+//!    window opens the overlay. Any other key path can later cancel the
+//!    prime.
+//! 2. **Second Esc** — moves `Primed` → `Selecting { selected_idx: 0 }`.
+//!    The live-transcript overlay opens with the most recent user message
+//!    highlighted. Left/Right step through prior user messages.
+//! 3. **Enter** — commits the selection: yields the chosen `selected_idx`
+//!    (a depth-from-tail offset, where `0` = newest user turn). Resets the
+//!    machine to `Inactive`. The caller then forks the thread, populates
+//!    the composer with the rolled-back text, and trims the transcript.
+//!
+//! The state machine knows nothing about the rest of the app — it stores
+//! only the small bookkeeping required to pick the right user turn. UI
+//! routing (popup detection, streaming guard, fork side effects) lives in
+//! `tui::ui`.
+
+#[derive(Debug, Clone, Copy, PartialEq, Eq, Default)]
+pub enum BacktrackPhase {
+    /// No prime in flight; Esc behaves normally.
+    #[default]
+    Inactive,
+    /// First Esc captured. The next Esc transitions into `Selecting`; any
+    /// other Esc-equivalent dismissal cancels back to `Inactive`.
+    Primed,
+    /// Overlay open. `selected_idx` is the depth-from-tail of the user
+    /// message currently highlighted (`0` = most recent). `total` is the
+    /// number of user messages available to step through, captured at
+    /// entry so bounds checks stay stable even if the transcript mutates
+    /// underneath the overlay (which it will, because the engine never
+    /// pauses).
+    Selecting { selected_idx: usize, total: usize },
+}
+
+#[derive(Debug, Clone, Copy, PartialEq, Eq)]
+pub enum Direction {
+    /// Step toward older user messages (increases `selected_idx`).
+    Left,
+    /// Step toward newer user messages (decreases `selected_idx`).
+    Right,
+}
+
+/// What the caller should do in response to a single `Esc` press.
+#[derive(Debug, Clone, Copy, PartialEq, Eq)]
+pub enum EscEffect {
+    /// No backtrack action — the caller should run its normal Esc path.
+    None,
+    /// Move from `Inactive` to `Primed`. The caller should surface the
+    /// transient prime hint.
+    Prime,
+    /// Cancel a Primed state without entering Selecting. The caller should
+    /// clear the prime hint.
+    Cancel,
+    /// Open the backtrack overlay (we transitioned `Primed` → `Selecting`).
+    /// The caller should push the live-transcript overlay in
+    /// `BacktrackPreview` mode.
+    OpenOverlay,
+}
+
+/// Small bookkeeping struct hung off `App`. Owns only the state machine —
+/// no transcript snapshots, no UI handles. The caller is responsible for
+/// telling the state machine how many user messages exist when entering
+/// `Selecting`, which avoids tying this module to any particular
+/// transcript representation.
+#[derive(Debug, Clone, Copy, PartialEq, Eq, Default)]
+pub struct BacktrackState {
+    pub phase: BacktrackPhase,
+}
+
+impl BacktrackState {
+    #[must_use]
+    pub fn new() -> Self {
+        Self {
+            phase: BacktrackPhase::Inactive,
+        }
+    }
+
+    /// `true` whenever the user has armed or opened backtrack. The UI uses
+    /// this to skip the prime hint once the overlay is up and to know
+    /// whether arrow keys should drive selection.
+    #[allow(dead_code)] // helper exposed for future UI consumers + tests.
+    #[must_use]
+    pub fn is_active(&self) -> bool {
+        !matches!(self.phase, BacktrackPhase::Inactive)
+    }
+
+    /// `true` only when the overlay is open and Left/Right should step
+    /// through prior user messages. `Primed` is intentionally excluded —
+    /// during the prime window arrows still scroll the transcript.
+    #[allow(dead_code)] // helper exposed for future UI consumers + tests.
+    #[must_use]
+    pub fn is_selecting(&self) -> bool {
+        matches!(self.phase, BacktrackPhase::Selecting { .. })
+    }
+
+    /// Current depth-from-tail offset, if any. Convenient for renderers
+    /// that need the highlight index without matching the enum.
+    #[must_use]
+    pub fn selected_idx(&self) -> Option<usize> {
+        match self.phase {
+            BacktrackPhase::Selecting { selected_idx, .. } => Some(selected_idx),
+            _ => None,
+        }
+    }
+
+    /// Process an Esc press.
+    ///
+    /// `total_user_messages` is the count of user turns in the live
+    /// transcript right now. It's only consulted on the `Primed` → `Selecting`
+    /// transition; a value of `0` short-circuits and cancels the prime
+    /// (nothing to backtrack to).
+    pub fn handle_esc(&mut self, total_user_messages: usize) -> EscEffect {
+        match self.phase {
+            BacktrackPhase::Inactive => {
+                if total_user_messages == 0 {
+                    // Nothing to backtrack to — do not even prime.
+                    return EscEffect::None;
+                }
+                self.phase = BacktrackPhase::Primed;
+                EscEffect::Prime
+            }
+            BacktrackPhase::Primed => {
+                if total_user_messages == 0 {
+                    self.phase = BacktrackPhase::Inactive;
+                    return EscEffect::Cancel;
+                }
+                self.phase = BacktrackPhase::Selecting {
+                    selected_idx: 0,
+                    total: total_user_messages,
+                };
+                EscEffect::OpenOverlay
+            }
+            BacktrackPhase::Selecting { .. } => {
+                // Esc while Selecting closes the overlay via the modal's own
+                // handler; it should not be routed back through here. Defend
+                // against accidental routing by canceling.
+                self.phase = BacktrackPhase::Inactive;
+                EscEffect::Cancel
+            }
+        }
+    }
+
+    /// Step the selection while in `Selecting`. No-op in any other phase.
+    /// `Left` walks backward in time (older), `Right` walks forward (newer).
+    /// Bounds-checked: `selected_idx` is clamped to `[0, total - 1]`.
+    pub fn step(&mut self, dir: Direction) {
+        if let BacktrackPhase::Selecting {
+            selected_idx,
+            total,
+        } = self.phase
+        {
+            if total == 0 {
+                return;
+            }
+            let last = total.saturating_sub(1);
+            let new_idx = match dir {
+                Direction::Left => selected_idx.saturating_add(1).min(last),
+                Direction::Right => selected_idx.saturating_sub(1),
+            };
+            self.phase = BacktrackPhase::Selecting {
+                selected_idx: new_idx,
+                total,
+            };
+        }
+    }
+
+    /// Commit the current selection. Returns the depth-from-tail offset
+    /// (0 = newest user turn) on success and resets to `Inactive`.
+    /// Returns `None` if not currently selecting — the caller should treat
+    /// it as a no-op.
+    pub fn confirm(&mut self) -> Option<usize> {
+        match self.phase {
+            BacktrackPhase::Selecting { selected_idx, .. } => {
+                self.phase = BacktrackPhase::Inactive;
+                Some(selected_idx)
+            }
+            _ => None,
+        }
+    }
+
+    /// Force the state machine back to `Inactive`. Used by the UI when a
+    /// popup steals focus, when streaming starts, when the overlay closes
+    /// without a confirm, and when any non-arrow / non-Enter key arrives
+    /// during `Primed`.
+    pub fn reset(&mut self) {
+        self.phase = BacktrackPhase::Inactive;
+    }
+}
+
+#[cfg(test)]
+mod tests {
+    use super::*;
+
+    #[test]
+    fn new_state_is_inactive() {
+        let s = BacktrackState::new();
+        assert!(!s.is_active());
+        assert!(!s.is_selecting());
+        assert_eq!(s.selected_idx(), None);
+    }
+
+    #[test]
+    fn first_esc_primes() {
+        let mut s = BacktrackState::new();
+        let effect = s.handle_esc(3);
+        assert_eq!(effect, EscEffect::Prime);
+        assert!(matches!(s.phase, BacktrackPhase::Primed));
+        assert!(s.is_active());
+        assert!(!s.is_selecting());
+    }
+
+    #[test]
+    fn first_esc_with_no_user_messages_is_noop() {
+        let mut s = BacktrackState::new();
+        let effect = s.handle_esc(0);
+        assert_eq!(effect, EscEffect::None);
+        assert!(matches!(s.phase, BacktrackPhase::Inactive));
+    }
+
+    #[test]
+    fn double_esc_enters_selecting() {
+        let mut s = BacktrackState::new();
+        assert_eq!(s.handle_esc(5), EscEffect::Prime);
+        let effect = s.handle_esc(5);
+        assert_eq!(effect, EscEffect::OpenOverlay);
+        assert_eq!(
+            s.phase,
+            BacktrackPhase::Selecting {
+                selected_idx: 0,
+                total: 5,
+            }
+        );
+        assert!(s.is_selecting());
+    }
+
+    #[test]
+    fn primed_with_zero_messages_cancels() {
+        // If the transcript empties between the first and second Esc (e.g.
+        // /clear ran in another path), the second Esc must cancel rather
+        // than open an empty overlay.
+        let mut s = BacktrackState::new();
+        s.phase = BacktrackPhase::Primed;
+        let effect = s.handle_esc(0);
+        assert_eq!(effect, EscEffect::Cancel);
+        assert!(matches!(s.phase, BacktrackPhase::Inactive));
+    }
+
+    #[test]
+    fn step_left_walks_back_in_time() {
+        let mut s = BacktrackState::new();
+        s.phase = BacktrackPhase::Selecting {
+            selected_idx: 0,
+            total: 3,
+        };
+        s.step(Direction::Left);
+        assert_eq!(s.selected_idx(), Some(1));
+        s.step(Direction::Left);
+        assert_eq!(s.selected_idx(), Some(2));
+        // Bounds: cannot go past `total - 1`.
+        s.step(Direction::Left);
+        assert_eq!(s.selected_idx(), Some(2));
+    }
+
+    #[test]
+    fn step_right_walks_forward_in_time() {
+        let mut s = BacktrackState::new();
+        s.phase = BacktrackPhase::Selecting {
+            selected_idx: 2,
+            total: 3,
+        };
+        s.step(Direction::Right);
+        assert_eq!(s.selected_idx(), Some(1));
+        s.step(Direction::Right);
+        assert_eq!(s.selected_idx(), Some(0));
+        // Bounds: saturating_sub keeps the floor at 0.
+        s.step(Direction::Right);
+        assert_eq!(s.selected_idx(), Some(0));
+    }
+
+    #[test]
+    fn step_in_inactive_or_primed_is_noop() {
+        let mut s = BacktrackState::new();
+        s.step(Direction::Left);
+        assert!(matches!(s.phase, BacktrackPhase::Inactive));
+        s.phase = BacktrackPhase::Primed;
+        s.step(Direction::Right);
+        assert!(matches!(s.phase, BacktrackPhase::Primed));
+    }
+
+    #[test]
+    fn step_with_total_one_clamps_at_zero() {
+        let mut s = BacktrackState::new();
+        s.phase = BacktrackPhase::Selecting {
+            selected_idx: 0,
+            total: 1,
+        };
+        s.step(Direction::Left);
+        assert_eq!(s.selected_idx(), Some(0));
+        s.step(Direction::Right);
+        assert_eq!(s.selected_idx(), Some(0));
+    }
+
+    #[test]
+    fn confirm_yields_index_and_resets() {
+        let mut s = BacktrackState::new();
+        s.phase = BacktrackPhase::Selecting {
+            selected_idx: 2,
+            total: 5,
+        };
+        let idx = s.confirm();
+        assert_eq!(idx, Some(2));
+        assert!(matches!(s.phase, BacktrackPhase::Inactive));
+    }
+
+    #[test]
+    fn confirm_outside_selecting_returns_none() {
+        let mut s = BacktrackState::new();
+        assert_eq!(s.confirm(), None);
+        s.phase = BacktrackPhase::Primed;
+        assert_eq!(s.confirm(), None);
+        assert!(matches!(s.phase, BacktrackPhase::Primed));
+    }
+
+    #[test]
+    fn reset_returns_to_inactive_from_any_phase() {
+        let mut s = BacktrackState::new();
+        s.phase = BacktrackPhase::Primed;
+        s.reset();
+        assert!(matches!(s.phase, BacktrackPhase::Inactive));
+
+        s.phase = BacktrackPhase::Selecting {
+            selected_idx: 1,
+            total: 3,
+        };
+        s.reset();
+        assert!(matches!(s.phase, BacktrackPhase::Inactive));
+    }
+
+    #[test]
+    fn esc_during_selecting_resets_defensively() {
+        // Routing Esc through the state machine while already selecting
+        // should not enter a fourth state — it cancels. The overlay's own
+        // Esc handler is the canonical close path, but we defend against
+        // a callsite that misroutes.
+        let mut s = BacktrackState::new();
+        s.phase = BacktrackPhase::Selecting {
+            selected_idx: 1,
+            total: 3,
+        };
+        let effect = s.handle_esc(3);
+        assert_eq!(effect, EscEffect::Cancel);
+        assert!(matches!(s.phase, BacktrackPhase::Inactive));
+    }
+
+    #[test]
+    fn primed_then_step_then_second_esc_reaches_selecting() {
+        // Steps that arrive while Primed should be no-ops on phase, so a
+        // subsequent Esc still completes the chord. (Practically this
+        // matters for the case where the user, for instance, pressed an
+        // arrow key while the prime hint was visible.)
+        let mut s = BacktrackState::new();
+        assert_eq!(s.handle_esc(2), EscEffect::Prime);
+        s.step(Direction::Left); // no-op
+        assert!(matches!(s.phase, BacktrackPhase::Primed));
+        assert_eq!(s.handle_esc(2), EscEffect::OpenOverlay);
+        assert_eq!(s.selected_idx(), Some(0));
+    }
+
+    #[test]
+    fn full_walk_then_confirm_returns_chosen_index() {
+        let mut s = BacktrackState::new();
+        assert_eq!(s.handle_esc(4), EscEffect::Prime);
+        assert_eq!(s.handle_esc(4), EscEffect::OpenOverlay);
+        s.step(Direction::Left); // 0 -> 1
+        s.step(Direction::Left); // 1 -> 2
+        assert_eq!(s.confirm(), Some(2));
+        assert!(matches!(s.phase, BacktrackPhase::Inactive));
+    }
+}
diff --git a/crates/tui/src/tui/mod.rs b/crates/tui/src/tui/mod.rs
index 5eeca1a1..cdaca726 100644
--- a/crates/tui/src/tui/mod.rs
+++ b/crates/tui/src/tui/mod.rs
@@ -5,6 +5,7 @@
 pub mod active_cell;
 pub mod app;
 pub mod approval;
+pub mod backtrack;
 pub mod clipboard;
 pub mod command_palette;
 pub mod diff_render;