diff --git a/playwright/e2e/permalinks/permalinks.spec.ts b/playwright/e2e/permalinks/permalinks.spec.ts
index e7657b1394..3f6fddbd0d 100644
--- a/playwright/e2e/permalinks/permalinks.spec.ts
+++ b/playwright/e2e/permalinks/permalinks.spec.ts
@@ -100,3 +100,51 @@ test.describe("permalinks", () => {
         });
     });
 });
+
+test.describe("triple-click message selection", () => {
+    test.use({
+        displayName: "Alice",
+    });
+
+    test("should select entire message line when triple-clicking on message with pills", async ({
+        page,
+        app,
+        user,
+        bot,
+    }) => {
+        await bot.prepareClient();
+
+        const roomId = await app.client.createRoom({ name: "Test Room" });
+        await app.client.inviteUser(roomId, bot.credentials.userId);
+        await app.viewRoomByName("Test Room");
+
+        // Send a message with user and room pills
+        await app.client.sendMessage(
+            roomId,
+            `Testing triple-click message selection. ` +
+                `User: ${permalinkPrefix}${bot.credentials.userId}, ` +
+                `Room: ${permalinkPrefix}${roomId}, ` +
+                `Message: ${permalinkPrefix}${roomId}/$dummy-event, ` +
+                `and @room mention.`,
+        );
+
+        const timeline = page.locator(".mx_RoomView_timeline");
+        const messageTile = timeline.locator(".mx_EventTile").last();
+
+        // Triple-click on the message body to select its entire content
+        const messageBody = messageTile.locator(".mx_EventTile_body");
+        await messageBody.click({ clickCount: 3 });
+
+        // Get the expected text content of the message, including pills
+        const expectedText = await messageBody.innerText();
+
+        // Get the currently selected text from the page
+        const selectedText = await page.evaluate(() => {
+            const selection = window.getSelection();
+            return selection ? selection.toString().trim() : "";
+        });
+
+        // Verify that the selected text exactly matches the message content
+        expect(selectedText).toBe(expectedText);
+    });
+});
diff --git a/res/css/views/elements/_Pill.pcss b/res/css/views/elements/_Pill.pcss
index d692f812a4..4b3fd3bb68 100644
--- a/res/css/views/elements/_Pill.pcss
+++ b/res/css/views/elements/_Pill.pcss
@@ -11,8 +11,7 @@ Please see LICENSE files in the repository root for full details.
     line-height: $font-17px;
     border-radius: $font-16px;
     vertical-align: text-top;
-    display: inline-flex;
-    align-items: center;
+    display: inline-block;
     box-sizing: border-box;
     max-width: 100%;
     overflow: hidden;
@@ -57,6 +56,8 @@ Please see LICENSE files in the repository root for full details.
         margin-inline-start: -0.3em; /* Otherwise the gap is too large */
         margin-inline-end: 0.2em;
         min-width: $font-16px; /* ensure the avatar is not compressed */
+        user-select: text;
+        vertical-align: -2.5px;
     }
 
     .mx_Pill_text {