diff --git a/editor/src/messages/tool/tool_messages/pen_tool.rs b/editor/src/messages/tool/tool_messages/pen_tool.rs
index 2aadd7e8523..1c30beb7d0e 100644
--- a/editor/src/messages/tool/tool_messages/pen_tool.rs
+++ b/editor/src/messages/tool/tool_messages/pen_tool.rs
@@ -1374,7 +1374,9 @@ impl PenToolData {
 	/// Perform extension of an existing path
 	fn extend_existing_path(&mut self, document: &DocumentMessageHandler, layer: LayerNodeIdentifier, point: PointId, position: DVec2) {
 		let vector: Option<VectorGeometry> = document.network_interface.compute_modified_vector(layer);
-		let (handle_start, in_segment) = if let Some(vector) = &vector {
+		let (handle_start, in_segment) = if let Some(vector) = &vector
+			&& vector.connected_count(point) <= 1
+		{
 			vector
 				.segment_iter()
 				.find_map(|(segment_id, bezier, start, end)| {
@@ -2393,13 +2395,14 @@ impl Fsm for PenToolFsmState {
 
 #[cfg(test)]
 mod test_pen_tool {
+	use super::is_almost_colinear;
 	use crate::messages::input_mapper::utility_types::pointer::EditorPointerState;
 	use crate::messages::portfolio::document::graph_operation::utility_types::TransformIn;
 	use crate::messages::tool::common_functionality::snap_session::WAKE_DWELL_ON_APPROACH;
 	use crate::test_utils::test_prelude::*;
 	use glam::DAffine2;
 	use graphene_std::vector::misc::ManipulatorPointId;
-	use graphene_std::vector::{SegmentId, VectorGeometry};
+	use graphene_std::vector::{PointId, SegmentId, VectorGeometry};
 
 	/// The single Pen-drawn path layer and its vector, or `None` once the layer has been undone away.
 	fn drawn_path(editor: &EditorTestUtils) -> Option<(LayerNodeIdentifier, VectorGeometry)> {
@@ -2970,6 +2973,37 @@ mod test_pen_tool {
 		assert!(leaving.distance(handle) < 1e-6, "the joining segment's handle is at {leaving}");
 	}
 
+	/// Finds the point ID whose viewport position is within tolerance of `target`.
+	fn get_anchor_near(vector: &VectorGeometry, layer_to_viewport: DAffine2, target: DVec2) -> PointId {
+		vector
+			.anchors()
+			.find(|&(_id, pos)| layer_to_viewport.transform_point2(pos).distance(target) < 1e-6)
+			.map(|(id, _pos)| id)
+			.unwrap_or_else(|| panic!("No anchor found near {target}"))
+	}
+
+	/// Finds the segment that connects two given point IDs (in either direction).
+	fn get_segment_between(vector: &VectorGeometry, point_a: PointId, point_b: PointId) -> SegmentId {
+		vector
+			.segment_ids()
+			.into_iter()
+			.find(|&segment| {
+				let start = vector.segment_start_from_id(segment);
+				let end = vector.segment_end_from_id(segment);
+				(start == Some(point_a) && end == Some(point_b)) || (start == Some(point_b) && end == Some(point_a))
+			})
+			.unwrap_or_else(|| panic!("No segment found between the given anchors"))
+	}
+
+	/// Finds the handle position on `segment` that corresponds to `point`.
+	fn get_handle_at(vector: &VectorGeometry, segment: SegmentId, point: PointId) -> Option<DVec2> {
+		if vector.segment_start_from_id(segment) == Some(point) {
+			vector.position_of(ManipulatorPointId::PrimaryHandle(segment))
+		} else {
+			vector.position_of(ManipulatorPointId::EndHandle(segment))
+		}
+	}
+
 	#[tokio::test]
 	async fn an_anchor_moved_with_space_lands_on_a_corner_and_carries_its_handles_along() {
 		let mut editor = EditorTestUtils::create();
@@ -3033,4 +3067,83 @@ mod test_pen_tool {
 		let outgoing = editor.active_document().metadata().transform_to_viewport(layer).transform_point2(outgoing);
 		assert!(outgoing.distance(handle + travel) < 1e-6, "the handle is at {outgoing} rather than {}", handle + travel);
 	}
+
+	#[tokio::test]
+	async fn extending_from_anchor_with_multiple_segments_does_not_create_colinear_handle() {
+		let mut editor = EditorTestUtils::create();
+		editor.new_document().await;
+
+		// 1. Draw a path through A, B, and C with curved handles dragged out at B
+		click_pen(&mut editor, A).await;
+		let handle = B + DVec2::new(50., 0.);
+		editor.drag_path(&[B, handle], ModifierKeys::empty()).await;
+		click_pen(&mut editor, C).await;
+		editor.press(Key::Enter, ModifierKeys::empty()).await;
+		assert_path_shape(&editor, 3, 2);
+
+		// 2. Extend from anchor B to D by clicking on B and then D (without dragging)
+		click_pen(&mut editor, B).await;
+		click_pen(&mut editor, D).await;
+		editor.press(Key::Enter, ModifierKeys::empty()).await;
+		assert_path_shape(&editor, 4, 3);
+
+		// 3. Verify the new branch leaving B does not create a mirrored/colinear handle
+		let (layer, vector) = drawn_path(&editor).expect("Expected a drawn path");
+		let layer_to_viewport = editor.active_document().metadata().transform_to_viewport(layer);
+
+		let b_id = get_anchor_near(&vector, layer_to_viewport, B);
+		let d_id = get_anchor_near(&vector, layer_to_viewport, D);
+		let bd_segment = get_segment_between(&vector, b_id, d_id);
+
+		if let Some(handle_pos) = get_handle_at(&vector, bd_segment, b_id) {
+			let handle_pos = layer_to_viewport.transform_point2(handle_pos);
+			assert!(handle_pos.distance(B) < 1e-4, "Handle at B for the new segment should remain at the anchor");
+		}
+	}
+
+	#[tokio::test]
+	async fn extending_from_anchor_with_single_segment_uses_colinear_handle() {
+		let mut editor = EditorTestUtils::create();
+		editor.new_document().await;
+
+		// 1. Draw a single segment A→B with a curved handle dragged out at B
+		click_pen(&mut editor, A).await;
+		let handle = B + DVec2::new(50., 0.);
+		editor.drag_path(&[B, handle], ModifierKeys::empty()).await;
+		editor.press(Key::Enter, ModifierKeys::empty()).await;
+		assert_path_shape(&editor, 2, 1);
+
+		// 2. Extend from B to C by clicking B then C (only one segment is attached to B)
+		click_pen(&mut editor, B).await;
+		click_pen(&mut editor, C).await;
+		editor.press(Key::Enter, ModifierKeys::empty()).await;
+		assert_path_shape(&editor, 3, 2);
+
+		// 3. Verify the new segment leaving B carries a mirrored/colinear handle
+		let (layer, vector) = drawn_path(&editor).expect("Expected a drawn path");
+		let layer_to_viewport = editor.active_document().metadata().transform_to_viewport(layer);
+
+		let b_id = get_anchor_near(&vector, layer_to_viewport, B);
+		let c_id = get_anchor_near(&vector, layer_to_viewport, C);
+		let bc_segment = get_segment_between(&vector, b_id, c_id);
+
+		let a_id = get_anchor_near(&vector, layer_to_viewport, A);
+		let ab_segment = get_segment_between(&vector, a_id, b_id);
+		let existing_handle_at_b = get_handle_at(&vector, ab_segment, b_id).expect("Segment AB should have a handle at B");
+		let existing_handle_pos = layer_to_viewport.transform_point2(existing_handle_at_b);
+
+		let new_handle_at_b = get_handle_at(&vector, bc_segment, b_id).expect("The new segment should have a handle at B");
+		let new_handle_pos = layer_to_viewport.transform_point2(new_handle_at_b);
+
+		// When only one segment is connected, the handle should not collapse to the
+		// anchor, and must be colinear with the existing handle at B.
+		assert!(
+			new_handle_pos.distance(B) > 1e-4,
+			"Handle at B should not collapse to the anchor when only one segment is connected (got {new_handle_pos})"
+		);
+		assert!(
+			is_almost_colinear(B, existing_handle_pos, new_handle_pos),
+			"New handle should be colinear with the existing handle at B (existing: {existing_handle_pos}, new: {new_handle_pos})"
+		);
+	}
 }