diff --git a/invokeai/frontend/web/src/features/controlLayers/konva/events.ts b/invokeai/frontend/web/src/features/controlLayers/konva/events.ts
index 95a5d8b3e8..4793faf7b7 100644
--- a/invokeai/frontend/web/src/features/controlLayers/konva/events.ts
+++ b/invokeai/frontend/web/src/features/controlLayers/konva/events.ts
@@ -6,6 +6,7 @@ import type {
   LayerEntity,
   Position,
   RegionEntity,
+  Tool,
 } from 'features/controlLayers/store/types';
 import { isDrawableEntity, isDrawableEntityAdapter } from 'features/controlLayers/store/types';
 import type Konva from 'konva';
@@ -64,6 +65,49 @@ const getNextPoint = (
   return currentPos;
 };
 
+const getLastPointOfLine = (points: number[]): Position | null => {
+  if (points.length < 2) {
+    return null;
+  }
+  const x = points[points.length - 2];
+  const y = points[points.length - 1];
+  if (x === undefined || y === undefined) {
+    return null;
+  }
+  return { x, y };
+};
+
+const getLastPointOfLastLineOfEntity = (
+  entity: LayerEntity | RegionEntity | InpaintMaskEntity,
+  tool: Tool
+): Position | null => {
+  const lastObject = entity.objects[entity.objects.length - 1];
+
+  if (!lastObject) {
+    return null;
+  }
+
+  if (
+    !(
+      (lastObject.type === 'brush_line' && tool === 'brush') ||
+      (lastObject.type === 'eraser_line' && tool === 'eraser')
+    )
+  ) {
+    // If the last object type and current tool do not match, we cannot continue the line
+    return null;
+  }
+
+  if (lastObject.points.length < 2) {
+    return null;
+  }
+  const x = lastObject.points[lastObject.points.length - 2];
+  const y = lastObject.points[lastObject.points.length - 1];
+  if (x === undefined || y === undefined) {
+    return null;
+  }
+  return { x, y };
+};
+
 export const setStageEventHandlers = (manager: CanvasManager): (() => void) => {
   const { stage, stateApi, getSelectedEntityAdapter } = manager;
   const {
@@ -75,7 +119,7 @@ export const setStageEventHandlers = (manager: CanvasManager): (() => void) => {
     setLastMouseDownPos,
     getLastCursorPos,
     setLastCursorPos,
-    getLastAddedPoint,
+    // getLastAddedPoint,
     setLastAddedPoint,
     setStageAttrs,
     getSelectedEntity,
@@ -137,27 +181,26 @@ export const setStageEventHandlers = (manager: CanvasManager): (() => void) => {
       setLastMouseDownPos(pos);
 
       if (toolState.selected === 'brush') {
-        if (e.evt.shiftKey) {
-          const lastAddedPoint = getLastAddedPoint();
-          // Create a straight line if holding shift
-          if (lastAddedPoint) {
-            if (selectedEntityAdapter.getDrawingBuffer()) {
-              selectedEntityAdapter.finalizeDrawingBuffer();
-            }
-            await selectedEntityAdapter.setDrawingBuffer({
-              id: getBrushLineId(selectedEntityAdapter.id, uuidv4()),
-              type: 'brush_line',
-              points: [
-                lastAddedPoint.x - selectedEntity.x,
-                lastAddedPoint.y - selectedEntity.y,
-                pos.x - selectedEntity.x,
-                pos.y - selectedEntity.y,
-              ],
-              strokeWidth: toolState.brush.width,
-              color: getCurrentFill(),
-              clip: getClip(selectedEntity),
-            });
+        const lastLinePoint = getLastPointOfLastLineOfEntity(selectedEntity, toolState.selected);
+        if (e.evt.shiftKey && lastLinePoint) {
+          // Create a straight line from the last line point
+          if (selectedEntityAdapter.getDrawingBuffer()) {
+            selectedEntityAdapter.finalizeDrawingBuffer();
           }
+          await selectedEntityAdapter.setDrawingBuffer({
+            id: getBrushLineId(selectedEntityAdapter.id, uuidv4()),
+            type: 'brush_line',
+            points: [
+              // The last point of the last line is already normalized to the entity's coordinates
+              lastLinePoint.x,
+              lastLinePoint.y,
+              pos.x - selectedEntity.x,
+              pos.y - selectedEntity.y,
+            ],
+            strokeWidth: toolState.brush.width,
+            color: getCurrentFill(),
+            clip: getClip(selectedEntity),
+          });
         } else {
           if (selectedEntityAdapter.getDrawingBuffer()) {
             selectedEntityAdapter.finalizeDrawingBuffer();
@@ -180,26 +223,25 @@ export const setStageEventHandlers = (manager: CanvasManager): (() => void) => {
       }
 
       if (toolState.selected === 'eraser') {
-        if (e.evt.shiftKey) {
-          // Create a straight line if holding shift
-          const lastAddedPoint = getLastAddedPoint();
-          if (lastAddedPoint) {
-            if (selectedEntityAdapter.getDrawingBuffer()) {
-              selectedEntityAdapter.finalizeDrawingBuffer();
-            }
-            await selectedEntityAdapter.setDrawingBuffer({
-              id: getBrushLineId(selectedEntityAdapter.id, uuidv4()),
-              type: 'eraser_line',
-              points: [
-                lastAddedPoint.x - selectedEntity.x,
-                lastAddedPoint.y - selectedEntity.y,
-                pos.x - selectedEntity.x,
-                pos.y - selectedEntity.y,
-              ],
-              strokeWidth: toolState.eraser.width,
-              clip: getClip(selectedEntity),
-            });
+        const lastLinePoint = getLastPointOfLastLineOfEntity(selectedEntity, toolState.selected);
+        if (e.evt.shiftKey && lastLinePoint) {
+          // Create a straight line from the last line point
+          if (selectedEntityAdapter.getDrawingBuffer()) {
+            selectedEntityAdapter.finalizeDrawingBuffer();
           }
+          await selectedEntityAdapter.setDrawingBuffer({
+            id: getBrushLineId(selectedEntityAdapter.id, uuidv4()),
+            type: 'eraser_line',
+            points: [
+              // The last point of the last line is already normalized to the entity's coordinates
+              lastLinePoint.x,
+              lastLinePoint.y,
+              pos.x - selectedEntity.x,
+              pos.y - selectedEntity.y,
+            ],
+            strokeWidth: toolState.eraser.width,
+            clip: getClip(selectedEntity),
+          });
         } else {
           if (selectedEntityAdapter.getDrawingBuffer()) {
             selectedEntityAdapter.finalizeDrawingBuffer();
@@ -308,8 +350,7 @@ export const setStageEventHandlers = (manager: CanvasManager): (() => void) => {
         const drawingBuffer = selectedEntityAdapter.getDrawingBuffer();
         if (drawingBuffer) {
           if (drawingBuffer?.type === 'brush_line') {
-            const lastAddedPoint = getLastAddedPoint();
-            const nextPoint = getNextPoint(pos, toolState, lastAddedPoint);
+            const nextPoint = getNextPoint(pos, toolState, getLastPointOfLine(drawingBuffer.points));
             if (nextPoint) {
               drawingBuffer.points.push(nextPoint.x - selectedEntity.x, nextPoint.y - selectedEntity.y);
               await selectedEntityAdapter.setDrawingBuffer(drawingBuffer);
@@ -343,8 +384,7 @@ export const setStageEventHandlers = (manager: CanvasManager): (() => void) => {
         const drawingBuffer = selectedEntityAdapter.getDrawingBuffer();
         if (drawingBuffer) {
           if (drawingBuffer.type === 'eraser_line') {
-            const lastAddedPoint = getLastAddedPoint();
-            const nextPoint = getNextPoint(pos, toolState, lastAddedPoint);
+            const nextPoint = getNextPoint(pos, toolState, getLastPointOfLine(drawingBuffer.points));
             if (nextPoint) {
               drawingBuffer.points.push(nextPoint.x - selectedEntity.x, nextPoint.y - selectedEntity.y);
               await selectedEntityAdapter.setDrawingBuffer(drawingBuffer);