diff --git a/crates/engine/src/snap/tracking.rs b/crates/engine/src/snap/tracking.rs
index e0740d7b..9db1873f 100644
--- a/crates/engine/src/snap/tracking.rs
+++ b/crates/engine/src/snap/tracking.rs
@@ -770,7 +770,8 @@ pub struct CursorQuery {
     pub tol: f64,
     /// Seconds on any steady clock (acquisition timing).
     pub now: f64,
-    /// Shift is held.
+    /// Shift is held: it overrides ortho for as long as it is held, and acquires tracking
+    /// points with POLARMODE bit 8.
     pub shift: bool,
 }
 
@@ -780,7 +781,10 @@ impl crate::Session {
     /// tracking, Extension, Parallel, Apparent Intersection), then ortho.
     pub fn snap_cursor(&mut self, raw: Vec2, q: &CursorQuery) -> CursorSnap {
         // Snap and grid spacing are the drawing's (SNAPUNIT/GRIDUNIT live in its header).
-        let s = self.drafting_settings();
+        let mut s = self.drafting_settings();
+        // Holding Shift overrides ortho while it is held: on when ORTHOMODE is off, off when it
+        // is on (ORTHOMODE itself is unchanged). Ortho on also turns polar tracking off.
+        s.orthomode ^= q.shift;
         let angbase = self.angle_settings().angbase;
         let Ok(st) = self.state() else { return CursorSnap { point: raw, ..Default::default() } };
         let (doc, space) = (st.doc.clone(), st.edit_space());
diff --git a/crates/engine/tests/snap_tracking.rs b/crates/engine/tests/snap_tracking.rs
index 2f2bbd90..3843002d 100644
--- a/crates/engine/tests/snap_tracking.rs
+++ b/crates/engine/tests/snap_tracking.rs
@@ -302,6 +302,39 @@ fn shift_to_acquire() {
     assert_eq!(s.tracking.acquired.len(), 1);
 }
 
+#[test]
+fn shift_overrides_ortho_while_held() {
+    let mut s = session(0);
+    let base = Some(v(0.0, 0.0));
+    let held = |base| CursorQuery { shift: true, ..query(base, 100.0) };
+    // Ortho off: Shift turns it on.
+    assert_eq!(at(&mut s, v(5.0, 1.0), base).point, v(5.0, 1.0));
+    assert_eq!(s.snap_cursor(v(5.0, 1.0), &held(base)).point, v(5.0, 0.0));
+    // Ortho on: Shift turns it off.
+    s.execute("ortho", &json!({ "on": true })).unwrap();
+    assert_eq!(at(&mut s, v(5.0, 1.0), base).point, v(5.0, 0.0));
+    assert_eq!(s.snap_cursor(v(5.0, 1.0), &held(base)).point, v(5.0, 1.0));
+    assert!(s.settings.orthomode, "the override leaves ORTHOMODE as it was");
+    // No base point, or a window's first corner: nothing to constrain.
+    assert_eq!(s.snap_cursor(v(5.0, 1.0), &held(None)).point, v(5.0, 1.0));
+    s.execute("ortho", &json!({ "on": false })).unwrap();
+    let corner = CursorQuery { corner: true, ..held(base) };
+    assert_eq!(s.snap_cursor(v(5.0, 1.0), &corner).point, v(5.0, 1.0));
+}
+
+#[test]
+fn shift_ortho_override_wins_over_polar() {
+    let mut s = session(0);
+    s.execute("polar", &json!({ "on": true })).unwrap();
+    setvar(&mut s, "POLARANG", json!(45));
+    let base = Some(v(0.0, 0.0));
+    // Near the 45° polar path the cursor follows it; with Shift held ortho does instead.
+    let free = at(&mut s, v(5.0, 5.05), base);
+    assert!(free.track.is_some() && free.point.near(v(5.025, 5.025), 1e-9), "{free:?}");
+    let held = s.snap_cursor(v(5.0, 5.05), &CursorQuery { shift: true, ..query(base, 100.0) });
+    assert_eq!((held.point, held.track), (v(0.0, 5.05), None));
+}
+
 #[test]
 fn sysvars_polarmode_polaraddang_autosnap() {
     let mut s = Session::new();
diff --git a/docs/ui-parity.md b/docs/ui-parity.md
index 3e3bac74..6776f70f 100644
--- a/docs/ui-parity.md
+++ b/docs/ui-parity.md
@@ -83,7 +83,7 @@ ignored; there are no context menus. Remaining: **≈ 110–170 Opus 5.5 hours**
 
 | Feature | AutoCAD | CADCraft |
 |---|---|---|
-| Ortho (F8) | yes | yes (`snap.rs:503`) |
+| Ortho (F8) | yes, Shift overrides it while held | yes; holding Shift turns it on or off while held (`Session::snap_cursor`, `snap/tracking.rs`) |
 | Polar tracking increment | yes | yes, measured from ANGBASE; dotted path and "Polar: d < a°" tooltip (`snap/tracking.rs`, `canvas.rs` `draw_tracking`) |
 | Additional polar angles, relative to last segment | yes | additional angles yes (POLARADDANG with POLARMODE 4); **relative to the last segment no** |
 | Polar distance snap (PolarSnap) | yes | **no** |
@@ -206,6 +206,7 @@ down-arrow options menu (DYNPROMPT), and DYNDIM.
 | 2026-10-13 | minor | Filled-region highlight boundaries are traversed in deterministic coordinate order, fixing dash-phase jumps on CPU hover/selection redraws and GPU highlight rebuilds; CPU dash-position, pixel and GPU mesh regressions |
 | 2026-10-14 | minor | Selection cycling (#1143): the list and badge of SELECTIONCYCLING, Shift+Space through overlapping objects (#1145) |
 | 2026-10-14 | minor | Hatch Edit dialog adds boundaries from picked points or closed objects and removes selected loops |
+| 2026-10-14 | minor | Holding Shift overrides ortho while it is held (on when ORTHOMODE is off, off when it is on), as in AutoCAD |
 | 2026-10-13 | minor | Options ▸ Selection adds Select using two clicks only; PICKDRAG 0 disables drag-window creation/completion, 2 preserves clicks or drag, and the preference survives restart; UI pointer and profile regressions |
 | 2026-10-12 | minor | Selected and hovered objects redrawn in the selection colour (text and arrowheads included); Options ▸ Selection laid out as AutoCAD's: Object grouping, Show grips, grip object limit, selection preview, Visual Effect Settings (selection area, preview filter) |
 | 2026-10-12 | minor | Animation effects (dialog and menu fades, smoothed wheel scrolling and ⌘/Ctrl+wheel zoom) follow the operating system's setting; View ▸ Accessibility ▸ Animation Effects chooses System, On or Off |