diff --git a/crates/tools/src/direct.rs b/crates/tools/src/direct.rs
index cf17647c..9020413f 100644
--- a/crates/tools/src/direct.rs
+++ b/crates/tools/src/direct.rs
@@ -32,7 +32,7 @@ use vectorcraft_geom::{Anchor, PathData, Point, Rect};
 
 use crate::bbox::move_delta;
 use crate::corners::{self, CornerDrag, over_widget};
-use crate::guides::{HandleSnap, PointSnap, Targets};
+use crate::guides::{HandleSnap, Leave, PointSnap, Targets};
 use crate::meshedit::MeshEdit;
 use crate::pathtype::{self, BracketDrag, over_bracket};
 use crate::rulerguide::GuideEdit;
@@ -428,12 +428,12 @@ impl Tool for DirectSelectionTool {
                     self.anchor_snap = Some(PointSnap::new(cx, || Targets::for_anchor_drag(cx.doc, cx.selection)));
                 }
                 let mut d = move_delta(start, p, ev.mods.shift);
-                // The grabbed anchor snaps and the others follow it; Shift keeps the angle instead.
+                // The grabbed anchor snaps and the others follow it. Shift keeps the move at its
+                // angle, and the anchor slides along it onto what Smart Guides find there (#886).
                 self.guides.clear();
-                if !ev.mods.shift
-                    && let Some(snap) = &self.anchor_snap
-                {
-                    let (q, guides) = snap.snap(cx, grab + d);
+                if let Some(snap) = &self.anchor_snap {
+                    let shift = ev.mods.shift.then(|| Leave::segment(cx, grab, true));
+                    let (q, guides) = snap.snap_from(cx, grab + (p - start), shift.as_ref());
                     (d, self.guides) = (q - grab, guides);
                 }
                 out.push(Action::Preview("path.moveAnchors".into(), json!({"dx": d.x, "dy": d.y})));
@@ -1022,10 +1022,16 @@ mod tests {
         // In line with B's own bottom-left corner, which stays put.
         let (v, labels) = drag(&mut t, &c, (300.0, 300.0), (303.0, 330.0), none);
         assert_eq!((v, labels), (json!({"dx": 0.0, "dy": 30.0}), vec!["align".to_string()]));
-        // Shift keeps the move at 45° steps, unsnapped.
-        let (v, labels) = drag(&mut t, &c, (300.0, 300.0), (203.0, 199.0), Mods { shift: true, ..none });
-        let s = move_delta(Point::new(300.0, 300.0), Point::new(203.0, 199.0), true);
-        assert_eq!((v, labels), (json!({"dx": s.x, "dy": s.y}), vec![]));
+        // Shift keeps the move at 45° steps and still snaps along that line (#886): on the
+        // diagonal from B's corner, onto A's bottom-right corner…
+        let shift = Mods { shift: true, ..none };
+        let (v, labels) = drag(&mut t, &c, (300.0, 300.0), (203.0, 199.0), shift);
+        let near = |v: &serde_json::Value, (x, y): (f64, f64)| (v["dx"].as_f64().unwrap() - x).hypot(v["dy"].as_f64().unwrap() - y) < 1e-9;
+        assert!(near(&v, (-100.0, -100.0)) && labels == ["anchor"], "{v} {labels:?}");
+        // …and with nothing in reach, at the pointer's distance along its angle.
+        let (v, labels) = drag(&mut t, &c, (300.0, 300.0), (380.0, 302.0), shift);
+        let s = move_delta(Point::new(300.0, 300.0), Point::new(380.0, 302.0), true);
+        assert!(near(&v, (s.x, s.y)) && labels.is_empty(), "{v} {labels:?}");
         // Two anchors: the one pressed on (B's top-right) lands on A's corner.
         let two = anchors_of(b, &[(0, 0), (0, 1)]);
         let c = cx(&d, &two, &p);