diff --git a/core/src/components/list/list.ios.scss b/core/src/components/list/list.ios.scss
index c0863aa7f9f..ffccb9345ff 100644
--- a/core/src/components/list/list.ios.scss
+++ b/core/src/components/list/list.ios.scss
@@ -19,12 +19,25 @@
   @include border-radius($list-inset-ios-border-radius);
 }
 
-.list-ios.list-inset ion-item:last-child {
+/**
+ * These selectors ensure the last item in the list
+ * has the correct border.
+ * We need to consider the following scenarios:
+ 1. The only item in a list.
+ 2. The last item in a list as long as it is not the only item.
+ 3. The item in the last item-sliding in a list.
+ * Note that we do not select ion-item:last-of-type
+ * because that will cause the borders to disappear on
+ * items in an item-sliding when the item is the last
+ * element in the item-sliding container.
+ */
+.list-ios.list-inset ion-item:only-child,
+.list-ios.list-inset ion-item:not(:only-of-type):last-of-type,
+.list-ios.list-inset ion-item-sliding:last-of-type ion-item {
   --border-width: 0;
   --inner-border-width: 0;
 }
 
-
 .list-ios.list-inset + ion-list.list-inset {
   @include margin(0, null, null, null);
 }
diff --git a/core/src/components/list/list.md.scss b/core/src/components/list/list.md.scss
index 2c5d896726a..8b408f781d6 100644
--- a/core/src/components/list/list.md.scss
+++ b/core/src/components/list/list.md.scss
@@ -23,12 +23,50 @@
   @include border-radius($list-inset-md-border-radius);
 }
 
-.list-md.list-inset ion-item:first-child {
+/**
+ * These selectors ensure the first item in the list
+ * has the correct radius.
+ * We need to consider the following scenarios:
+ 1. The first item in a list as long as it is not the only item.
+ 2. The item in the first item-sliding in a list.
+ * Note that we do not select "ion-item-sliding ion-item:first-of-type"
+ * because that will cause the borders to disappear on
+ * items in an item-sliding when the item is the first
+ * element in the item-sliding container.
+ */
+.list-md.list-inset ion-item:not(:only-of-type):first-of-type,
+.list-md.list-inset ion-item-sliding:first-of-type ion-item {
   --border-radius: #{$list-inset-md-border-radius $list-inset-md-border-radius 0 0};
 }
 
-.list-md.list-inset ion-item:last-child {
-  --border-radius: #{0 0 $list-inset-md-border-radius, $list-inset-md-border-radius};
+/**
+ * These selectors ensure the last item in the list
+ * has the correct radius and border.
+ * We need to consider the following scenarios:
+ 1. The last item in a list as long as it is not the only item.
+ 2. The item in the last item-sliding in a list.
+ * Note that we do not select "ion-item-sliding ion-item:last-of-type"
+ * because that will cause the borders to disappear on
+ * items in an item-sliding when the item is the last
+ * element in the item-sliding container.
+ */
+.list-md.list-inset ion-item:not(:only-of-type):last-of-type,
+.list-md.list-inset ion-item-sliding:last-of-type ion-item {
+  --border-radius: #{0 0 $list-inset-md-border-radius $list-inset-md-border-radius};
+  --border-width: 0;
+  --inner-border-width: 0;
+}
+
+/**
+ * The only item in a list should have a border radius
+ * on all corners.
+ * We target :only-child instead of :only-of-type
+ * otherwise borders will disappear on items inside of
+ * ion-item-sliding because the item will be the only
+ * one of its type inside of the ion-item-sliding group.
+ */
+.list-md.list-inset ion-item:only-child {
+  --border-radius: #{$list-inset-md-border-radius};
   --border-width: 0;
   --inner-border-width: 0;
 }
diff --git a/core/src/components/list/test/lines/list.e2e.ts b/core/src/components/list/test/lines/list.e2e.ts
index c784fe5fe93..96265112c1d 100644
--- a/core/src/components/list/test/lines/list.e2e.ts
+++ b/core/src/components/list/test/lines/list.e2e.ts
@@ -26,3 +26,162 @@ configs().forEach(({ title, screenshot, config }) => {
     });
   });
 });
+
+/**
+ * Padding and border color ensures the bottom border can be easily seen if it regresses.
+ * The background color ensures that any border radius values can be seen.
+ */
+configs({ directions: ['ltr'] }).forEach(({ title, screenshot, config }) => {
+  test.describe(title('list: lines with children'), () => {
+    test('only item in inset list should not have line', async ({ page }) => {
+      test.info().annotations.push({
+        type: 'issue',
+        description: 'https://github.com/ionic-team/ionic-framework/issues/28435',
+      });
+      await page.setContent(
+        `
+        <style>
+          #container {
+            padding: 10px;
+            background: #0088cc;
+          }
+
+          ion-item {
+            --border-color: red;
+          }
+        </style>
+        <div id="container">
+          <ion-list inset="true">
+            <ion-item>
+              <ion-label>Item 0</ion-label>
+            </ion-item>
+          </ion-list>
+        </div>
+      `,
+        config
+      );
+
+      const container = page.locator('#container');
+
+      await expect(container).toHaveScreenshot(screenshot('inset-list-only-item-no-lines'));
+    });
+    test('last item in inset list with end options should not have line', async ({ page }) => {
+      test.info().annotations.push({
+        type: 'issue',
+        description: 'https://github.com/ionic-team/ionic-framework/issues/28435',
+      });
+      await page.setContent(
+        `
+        <style>
+          #container {
+            padding: 10px;
+            background: #0088cc;
+          }
+
+          ion-item {
+            --border-color: red;
+          }
+        </style>
+        <div id="container">
+          <ion-list inset="true">
+            <ion-item-sliding>
+              <ion-item>
+                <ion-label>Item 0</ion-label>
+              </ion-item>
+              <ion-item-options slot="end">
+                <ion-item-option color="warning">
+                  <ion-icon slot="icon-only" name="pin"></ion-icon>
+                </ion-item-option>
+              </ion-item-options>
+            </ion-item-sliding>
+
+            <ion-item-sliding>
+              <ion-item>
+                <ion-label>Item 1</ion-label>
+              </ion-item>
+              <ion-item-options slot="end">
+                <ion-item-option color="warning">
+                  <ion-icon slot="icon-only" name="pin"></ion-icon>
+                </ion-item-option>
+              </ion-item-options>
+            </ion-item-sliding>
+
+            <ion-item-sliding>
+              <ion-item>
+                <ion-label>Item 2</ion-label>
+              </ion-item>
+              <ion-item-options slot="end">
+                <ion-item-option color="warning">
+                  <ion-icon slot="icon-only" name="pin"></ion-icon>
+                </ion-item-option>
+              </ion-item-options>
+            </ion-item-sliding>
+          </ion-list>
+        </div>
+      `,
+        config
+      );
+
+      const container = page.locator('#container');
+
+      await expect(container).toHaveScreenshot(screenshot('inset-list-end-options-no-lines'));
+    });
+    test('last item in inset list with start options should not have line', async ({ page }) => {
+      await page.setContent(
+        `
+        <style>
+          #container {
+            padding: 10px;
+            background: #0088cc;
+          }
+
+          ion-item {
+            --border-color: red;
+          }
+        </style>
+        <div id="container">
+          <ion-list inset="true">
+            <ion-item-sliding>
+              <ion-item-options slot="start">
+                <ion-item-option color="warning">
+                  <ion-icon slot="icon-only" name="pin"></ion-icon>
+                </ion-item-option>
+              </ion-item-options>
+              <ion-item>
+                <ion-label>Item 0</ion-label>
+              </ion-item>
+            </ion-item-sliding>
+
+            <ion-item-sliding>
+              <ion-item-options slot="start">
+                <ion-item-option color="warning">
+                  <ion-icon slot="icon-only" name="pin"></ion-icon>
+                </ion-item-option>
+              </ion-item-options>
+              <ion-item>
+                <ion-label>Item 1</ion-label>
+              </ion-item>
+            </ion-item-sliding>
+
+            <ion-item-sliding>
+              <ion-item-options slot="start">
+                <ion-item-option color="warning">
+                  <ion-icon slot="icon-only" name="pin"></ion-icon>
+                </ion-item-option>
+              </ion-item-options>
+              <ion-item>
+                <ion-label>Item 2</ion-label>
+              </ion-item>
+            </ion-item-sliding>
+          </ion-list>
+        </div>
+      `,
+        config
+      );
+
+      const container = page.locator('#container');
+
+      await expect(container).toHaveScreenshot(screenshot('inset-list-start-options-no-lines'));
+    });
+  });
+});
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