diff --git a/core/src/components/checkbox/checkbox.scss b/core/src/components/checkbox/checkbox.scss
index b351d5f546..11364b42c3 100644
--- a/core/src/components/checkbox/checkbox.scss
+++ b/core/src/components/checkbox/checkbox.scss
@@ -52,6 +52,11 @@
  */
 :host([slot="start"]),
 :host([slot="end"]) {
+  // Reset the flex property when the checkbox
+  // is slotted to avoid growing the element larger
+  // than its content.
+  flex: initial;
+
   width: auto;
 }
 
diff --git a/core/src/components/item/test/inputs/item.e2e.ts b/core/src/components/item/test/inputs/item.e2e.ts
index 4e50d5303c..27ca3149b9 100644
--- a/core/src/components/item/test/inputs/item.e2e.ts
+++ b/core/src/components/item/test/inputs/item.e2e.ts
@@ -200,3 +200,57 @@ configs({ modes: ['ios'], directions: ['ltr'] }).forEach(({ title, config }) =>
     });
   });
 });
+
+/**
+ * This behavior does not vary across directions
+ */
+configs({ directions: ['ltr'] }).forEach(({ title, screenshot, config }) => {
+  test.describe(title('item: inputs'), () => {
+    test('should not shrink the width of a div next to a checkbox, radio, select or toggle', async ({
+      page,
+    }, testInfo) => {
+      testInfo.annotations.push({
+        type: 'issue',
+        description: 'https://github.com/ionic-team/ionic-framework/issues/29319',
+      });
+      await page.setContent(
+        `
+        <style>
+          .box {
+            background: lightgreen;
+
+            width: 60px;
+            height: 60px;
+          }
+        </style>
+
+        <ion-list lines="none">
+          <ion-item>
+            <div class="box"></div>
+            <ion-checkbox>Checkbox</ion-checkbox>
+          </ion-item>
+          <ion-item>
+            <div class="box"></div>
+            <ion-radio>Radio</ion-radio>
+          </ion-item>
+          <ion-item>
+            <div class="box"></div>
+            <ion-select label="Select">
+              <ion-select-option>Option</ion-select-option>
+            </ion-select>
+          </ion-item>
+          <ion-item>
+            <div class="box"></div>
+            <ion-toggle>Toggle</ion-toggle>
+          </ion-item>
+        </ion-list>
+      `,
+        config
+      );
+
+      const list = page.locator('ion-list');
+
+      await expect(list).toHaveScreenshot(screenshot(`item-inputs-div-with-inputs`));
+    });
+  });
+});
diff --git a/core/src/components/item/test/inputs/item.e2e.ts-snapshots/item-inputs-div-with-inputs-ios-ltr-Mobile-Chrome-linux.png b/core/src/components/item/test/inputs/item.e2e.ts-snapshots/item-inputs-div-with-inputs-ios-ltr-Mobile-Chrome-linux.png
new file mode 100644
index 0000000000..67d0ffd9bb
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diff --git a/core/src/components/item/test/inputs/item.e2e.ts-snapshots/item-inputs-div-with-inputs-ios-ltr-Mobile-Firefox-linux.png b/core/src/components/item/test/inputs/item.e2e.ts-snapshots/item-inputs-div-with-inputs-ios-ltr-Mobile-Firefox-linux.png
new file mode 100644
index 0000000000..624b20210e
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diff --git a/core/src/components/item/test/inputs/item.e2e.ts-snapshots/item-inputs-div-with-inputs-ios-ltr-Mobile-Safari-linux.png b/core/src/components/item/test/inputs/item.e2e.ts-snapshots/item-inputs-div-with-inputs-ios-ltr-Mobile-Safari-linux.png
new file mode 100644
index 0000000000..539832327f
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diff --git a/core/src/components/item/test/inputs/item.e2e.ts-snapshots/item-inputs-div-with-inputs-md-ltr-Mobile-Chrome-linux.png b/core/src/components/item/test/inputs/item.e2e.ts-snapshots/item-inputs-div-with-inputs-md-ltr-Mobile-Chrome-linux.png
new file mode 100644
index 0000000000..b0d5bde4d7
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diff --git a/core/src/components/item/test/inputs/item.e2e.ts-snapshots/item-inputs-div-with-inputs-md-ltr-Mobile-Firefox-linux.png b/core/src/components/item/test/inputs/item.e2e.ts-snapshots/item-inputs-div-with-inputs-md-ltr-Mobile-Firefox-linux.png
new file mode 100644
index 0000000000..f440ae41a7
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diff --git a/core/src/components/item/test/inputs/item.e2e.ts-snapshots/item-inputs-div-with-inputs-md-ltr-Mobile-Safari-linux.png b/core/src/components/item/test/inputs/item.e2e.ts-snapshots/item-inputs-div-with-inputs-md-ltr-Mobile-Safari-linux.png
new file mode 100644
index 0000000000..eafd009d1d
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diff --git a/core/src/components/item/test/slotted-inputs/item.e2e.ts b/core/src/components/item/test/slotted-inputs/item.e2e.ts
index eef05ce3ab..7fcbf4b8b1 100644
--- a/core/src/components/item/test/slotted-inputs/item.e2e.ts
+++ b/core/src/components/item/test/slotted-inputs/item.e2e.ts
@@ -12,3 +12,163 @@ configs().forEach(({ title, screenshot, config }) => {
     });
   });
 });
+
+/**
+ * This behavior does not vary across directions
+ */
+configs({ directions: ['ltr'] }).forEach(({ title, screenshot, config }) => {
+  test.describe(title('item: slotted inputs'), () => {
+    test.describe('checkbox', () => {
+      test('should not expand the slotted checkbox width larger than its content', async ({ page }, testInfo) => {
+        testInfo.annotations.push({
+          type: 'issue',
+          description: 'https://github.com/ionic-team/ionic-framework/issues/29423',
+        });
+
+        await page.setContent(
+          `
+          <ion-list>
+            <ion-item>
+              <ion-checkbox slot="start"></ion-checkbox>
+              <ion-label>Label</ion-label>
+            </ion-item>
+            <ion-item>
+              <ion-label>Label</ion-label>
+              <ion-checkbox slot="end"></ion-checkbox>
+            </ion-item>
+            <ion-item>
+              <ion-checkbox slot="start">Start</ion-checkbox>
+              <ion-label>Label</ion-label>
+            </ion-item>
+            <ion-item>
+              <ion-label>Label</ion-label>
+              <ion-checkbox slot="end">End</ion-checkbox>
+            </ion-item>
+          </ion-list>
+        `,
+          config
+        );
+
+        const list = page.locator('ion-list');
+
+        await expect(list).toHaveScreenshot(screenshot(`item-slotted-inputs-checkbox`));
+      });
+    });
+    test.describe('radio', () => {
+      test('should not expand the slotted radio width larger than its content', async ({ page }, testInfo) => {
+        testInfo.annotations.push({
+          type: 'issue',
+          description: 'https://github.com/ionic-team/ionic-framework/issues/29423',
+        });
+
+        await page.setContent(
+          `
+          <ion-list>
+            <ion-item>
+              <ion-radio slot="start"></ion-radio>
+              <ion-label>Label</ion-label>
+            </ion-item>
+            <ion-item>
+              <ion-label>Label</ion-label>
+              <ion-radio slot="end"></ion-radio>
+            </ion-item>
+            <ion-item>
+              <ion-radio slot="start">Start</ion-radio>
+              <ion-label>Label</ion-label>
+            </ion-item>
+            <ion-item>
+              <ion-label>Label</ion-label>
+              <ion-radio slot="end">End</ion-radio>
+            </ion-item>
+          </ion-list>
+        `,
+          config
+        );
+
+        const list = page.locator('ion-list');
+
+        await expect(list).toHaveScreenshot(screenshot(`item-slotted-inputs-radio`));
+      });
+    });
+    test.describe('select', () => {
+      test('should not expand the slotted select width larger than its content', async ({ page }, testInfo) => {
+        testInfo.annotations.push({
+          type: 'issue',
+          description: 'https://github.com/ionic-team/ionic-framework/issues/29423',
+        });
+
+        await page.setContent(
+          `
+          <ion-list>
+            <ion-item>
+              <ion-select slot="start">
+                <ion-select-option>Option</ion-select-option>
+              </ion-select>
+              <ion-label>Label</ion-label>
+            </ion-item>
+            <ion-item>
+              <ion-label>Label</ion-label>
+              <ion-select slot="end">
+                <ion-select-option>Option</ion-select-option>
+              </ion-select>
+            </ion-item>
+            <ion-item>
+              <ion-select slot="start" label="Start">
+                <ion-select-option>Option</ion-select-option>
+              </ion-select>
+              <ion-label>Label</ion-label>
+            </ion-item>
+            <ion-item>
+              <ion-label>Label</ion-label>
+              <ion-select slot="end" label="End">
+                <ion-select-option>Option</ion-select-option>
+              </ion-select>
+            </ion-item>
+          </ion-list>
+        `,
+          config
+        );
+
+        const list = page.locator('ion-list');
+
+        await expect(list).toHaveScreenshot(screenshot(`item-slotted-inputs-select`));
+      });
+    });
+    test.describe('toggle', () => {
+      test('should not expand the slotted toggle width larger than its content', async ({ page }, testInfo) => {
+        testInfo.annotations.push({
+          type: 'issue',
+          description: 'https://github.com/ionic-team/ionic-framework/issues/29423',
+        });
+
+        await page.setContent(
+          `
+          <ion-list>
+            <ion-item>
+              <ion-toggle slot="start"></ion-toggle>
+              <ion-label>Label</ion-label>
+            </ion-item>
+            <ion-item>
+              <ion-label>Label</ion-label>
+              <ion-toggle slot="end"></ion-toggle>
+            </ion-item>
+            <ion-item>
+              <ion-toggle slot="start">Start</ion-toggle>
+              <ion-label>Label</ion-label>
+            </ion-item>
+            <ion-item>
+              <ion-label>Label</ion-label>
+              <ion-toggle slot="end">End</ion-toggle>
+            </ion-item>
+          </ion-list>
+        `,
+          config
+        );
+
+        const list = page.locator('ion-list');
+
+        await expect(list).toHaveScreenshot(screenshot(`item-slotted-inputs-toggle`));
+      });
+    });
+  });
+});
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diff --git a/core/src/components/item/test/slotted-inputs/item.e2e.ts-snapshots/item-slotted-inputs-toggle-md-ltr-Mobile-Safari-linux.png b/core/src/components/item/test/slotted-inputs/item.e2e.ts-snapshots/item-slotted-inputs-toggle-md-ltr-Mobile-Safari-linux.png
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diff --git a/core/src/components/radio/radio.scss b/core/src/components/radio/radio.scss
index 159bde9262..2f70b3b2ee 100644
--- a/core/src/components/radio/radio.scss
+++ b/core/src/components/radio/radio.scss
@@ -72,6 +72,11 @@ input {
  */
 :host([slot="start"]),
 :host([slot="end"]) {
+  // Reset the flex property when the checkbox
+  // is slotted to avoid growing the element larger
+  // than its content.
+  flex: initial;
+
   width: auto;
 }
 
diff --git a/core/src/components/select/select.scss b/core/src/components/select/select.scss
index f564eec0ee..2ed4deee59 100644
--- a/core/src/components/select/select.scss
+++ b/core/src/components/select/select.scss
@@ -100,6 +100,11 @@
  */
 :host([slot="start"]),
 :host([slot="end"]) {
+  // Reset the flex property when the checkbox
+  // is slotted to avoid growing the element larger
+  // than its content.
+  flex: initial;
+
   width: auto;
 }
 
diff --git a/core/src/components/toggle/toggle.scss b/core/src/components/toggle/toggle.scss
index 90d4312146..9ea144a85b 100644
--- a/core/src/components/toggle/toggle.scss
+++ b/core/src/components/toggle/toggle.scss
@@ -53,6 +53,11 @@
  */
 :host([slot="start"]),
 :host([slot="end"]) {
+  // Reset the flex property when the checkbox
+  // is slotted to avoid growing the element larger
+  // than its content.
+  flex: initial;
+
   width: auto;
 }