diff --git a/src/display/annotation_layer.js b/src/display/annotation_layer.js
index e2dc138a8..fdfdf7e26 100644
--- a/src/display/annotation_layer.js
+++ b/src/display/annotation_layer.js
@@ -2815,37 +2815,48 @@ class InkAnnotationElement extends AnnotationElement {
     // Create an invisible polyline with the same points that acts as the
     // trigger for the popup.
     const {
-      data: { rect, inkLists, borderStyle, popupRef },
+      data: { rect, rotation, inkLists, borderStyle, popupRef },
     } = this;
-    const { width, height } = getRectDims(rect);
+    let { width, height } = getRectDims(rect);
+    let transform;
+
+    // PDF coordinates are calculated from a bottom left origin, so
+    // transform the polyline coordinates to a top left origin for the
+    // SVG element.
+    switch (rotation) {
+      case 90:
+        transform = `rotate(90) translate(${-rect[0]},${rect[3] - height}) scale(1,-1)`;
+        [width, height] = [height, width];
+        break;
+      case 180:
+        transform = `rotate(180) translate(${-rect[0] - width},${rect[3] - height}) scale(1,-1)`;
+        break;
+      case 270:
+        transform = `rotate(270) translate(${-rect[0] - width},${rect[3]}) scale(1,-1)`;
+        [width, height] = [height, width];
+        break;
+      default:
+        transform = `translate(${-rect[0]},${rect[3]}) scale(1,-1)`;
+        break;
+    }
+
     const svg = this.svgFactory.create(
       width,
       height,
       /* skipDimensions = */ true
     );
+    const basePolyline = this.svgFactory.createElement(this.svgElementName);
+    // Ensure that the 'stroke-width' is always non-zero, since otherwise it
+    // won't be possible to open/close the popup (note e.g. issue 11122).
+    basePolyline.setAttribute("stroke-width", borderStyle.width || 1);
+    basePolyline.setAttribute("stroke", "transparent");
+    basePolyline.setAttribute("fill", "transparent");
+    basePolyline.setAttribute("transform", transform);
 
-    for (const inkList of inkLists) {
-      // Convert the ink list to a single points string that the SVG
-      // polyline element expects ("x1,y1 x2,y2 ..."). PDF coordinates are
-      // calculated from a bottom left origin, so transform the polyline
-      // coordinates to a top left origin for the SVG element.
-      let points = [];
-      for (let i = 0, ii = inkList.length; i < ii; i += 2) {
-        const x = inkList[i] - rect[0];
-        const y = rect[3] - inkList[i + 1];
-        points.push(`${x},${y}`);
-      }
-      points = points.join(" ");
-
-      const polyline = this.svgFactory.createElement(this.svgElementName);
+    for (let i = 0, ii = inkLists.length; i < ii; i++) {
+      const polyline = i < ii - 1 ? basePolyline.cloneNode() : basePolyline;
       this.#polylines.push(polyline);
-      polyline.setAttribute("points", points);
-      // Ensure that the 'stroke-width' is always non-zero, since otherwise it
-      // won't be possible to open/close the popup (note e.g. issue 11122).
-      polyline.setAttribute("stroke-width", borderStyle.width || 1);
-      polyline.setAttribute("stroke", "transparent");
-      polyline.setAttribute("fill", "transparent");
-
+      polyline.setAttribute("points", inkLists[i].join(","));
       svg.append(polyline);
     }
 
diff --git a/test/integration/annotation_spec.mjs b/test/integration/annotation_spec.mjs
index 52e33698d..7431a17d1 100644
--- a/test/integration/annotation_spec.mjs
+++ b/test/integration/annotation_spec.mjs
@@ -16,6 +16,7 @@
 import {
   closePages,
   getQuerySelector,
+  getRect,
   getSelector,
   loadAndWait,
 } from "./test_utils.mjs";
@@ -654,4 +655,38 @@ describe("ResetForm action", () => {
       });
     });
   });
+
+  describe("Rotated annotation and its clickable area", () => {
+    describe("issue14438.pdf", () => {
+      let pages;
+
+      beforeAll(async () => {
+        pages = await loadAndWait(
+          "rotated_ink.pdf",
+          "[data-annotation-id='18R']"
+        );
+      });
+
+      afterAll(async () => {
+        await closePages(pages);
+      });
+
+      it("must check that the clickable area has been rotated", async () => {
+        await Promise.all(
+          pages.map(async ([browserName, page]) => {
+            const rect = await getRect(page, "[data-annotation-id='18R']");
+            const promisePopup = page.waitForSelector(
+              "[data-annotation-id='19R']",
+              { visible: true }
+            );
+            await page.mouse.move(
+              rect.x + rect.width * 0.1,
+              rect.y + rect.height * 0.9
+            );
+            await promisePopup;
+          })
+        );
+      });
+    });
+  });
 });
diff --git a/test/pdfs/.gitignore b/test/pdfs/.gitignore
index 9419dafdc..45949cc35 100644
--- a/test/pdfs/.gitignore
+++ b/test/pdfs/.gitignore
@@ -684,3 +684,4 @@
 !issue19083.pdf
 !issue19120.pdf
 !bug1934157.pdf
+!rotated_ink.pdf
diff --git a/test/pdfs/rotated_ink.pdf b/test/pdfs/rotated_ink.pdf
new file mode 100644
index 000000000..8b69361ea
Binary files /dev/null and b/test/pdfs/rotated_ink.pdf differ