diff --git a/packages/design-system/src/components/N8nMarkdown/Markdown.vue b/packages/design-system/src/components/N8nMarkdown/Markdown.vue
index 767dcae49e..4194a88f3a 100644
--- a/packages/design-system/src/components/N8nMarkdown/Markdown.vue
+++ b/packages/design-system/src/components/N8nMarkdown/Markdown.vue
@@ -5,6 +5,8 @@
 			ref="editor"
 			:class="$style[theme]"
 			@click="onClick"
+			@mousedown="onMouseDown"
+			@change="onChange"
 			v-html="htmlContent"
 		/>
 		<div v-else :class="$style.markdown">
@@ -17,7 +19,7 @@
 </template>
 
 <script lang="ts" setup>
-import { computed } from 'vue';
+import { computed, ref } from 'vue';
 import type { Options as MarkdownOptions } from 'markdown-it';
 import Markdown from 'markdown-it';
 import markdownLink from 'markdown-it-link-attributes';
@@ -26,7 +28,7 @@ import markdownTaskLists from 'markdown-it-task-lists';
 import xss, { friendlyAttrValue, whiteList } from 'xss';
 
 import N8nLoading from '../N8nLoading';
-import { escapeMarkdown } from '../../utils/markdown';
+import { escapeMarkdown, toggleCheckbox } from '../../utils/markdown';
 
 interface IImage {
 	id: string;
@@ -79,6 +81,8 @@ const props = withDefaults(defineProps<MarkdownProps>(), {
 	}),
 });
 
+const editor = ref<HTMLDivElement | undefined>(undefined);
+
 const { options } = props;
 const md = new Markdown(options.markdown)
 	.use(markdownLink, options.linkAttributes)
@@ -151,7 +155,7 @@ const htmlContent = computed(() => {
 	return safeHtml;
 });
 
-const $emit = defineEmits(['markdown-click']);
+const $emit = defineEmits(['markdown-click', 'update-content']);
 const onClick = (event: MouseEvent) => {
 	let clickedLink: HTMLAnchorElement | null = null;
 
@@ -167,6 +171,40 @@ const onClick = (event: MouseEvent) => {
 	}
 	$emit('markdown-click', clickedLink, event);
 };
+
+// Handle checkbox changes
+const onChange = async (event: Event) => {
+	if (event.target instanceof HTMLInputElement && event.target.type === 'checkbox') {
+		const checkboxes = editor.value?.querySelectorAll('input[type="checkbox"]');
+		if (checkboxes) {
+			// Get the index of the checkbox that was clicked
+			const index = Array.from(checkboxes).indexOf(event.target);
+			if (index !== -1) {
+				onCheckboxChange(index);
+			}
+		}
+	}
+};
+
+const onMouseDown = (event: MouseEvent) => {
+	// Mouse down on input fields is caught by node view handlers
+	// which prevents checking them, this will prevent that
+	if (event.target instanceof HTMLInputElement) {
+		event.stopPropagation();
+	}
+};
+
+// Update markdown when checkbox state changes
+const onCheckboxChange = (index: number) => {
+	const currentContent = props.content;
+	if (!currentContent) {
+		return;
+	}
+
+	// We are using index to connect the checkbox with the corresponding line in the markdown
+	const newContent = toggleCheckbox(currentContent, index);
+	$emit('update-content', newContent);
+};
 </script>
 
 <style lang="scss" module>
@@ -243,6 +281,14 @@ const onClick = (event: MouseEvent) => {
 	}
 }
 
+input[type='checkbox'] {
+	accent-color: var(--color-primary);
+}
+
+input[type='checkbox'] + label {
+	cursor: pointer;
+}
+
 .sticky {
 	color: var(--color-sticky-font);
 
@@ -297,6 +343,11 @@ const onClick = (event: MouseEvent) => {
 			font-weight: var(--font-weight-regular);
 			line-height: var(--font-line-height-regular);
 		}
+
+		&:has(input[type='checkbox']) {
+			list-style-type: none;
+			padding-left: var(--spacing-5xs);
+		}
 	}
 
 	code {
diff --git a/packages/design-system/src/components/N8nMarkdown/__tests__/Markdown.spec.ts b/packages/design-system/src/components/N8nMarkdown/__tests__/Markdown.spec.ts
index b0c76ee45d..2c826f5192 100644
--- a/packages/design-system/src/components/N8nMarkdown/__tests__/Markdown.spec.ts
+++ b/packages/design-system/src/components/N8nMarkdown/__tests__/Markdown.spec.ts
@@ -1,4 +1,4 @@
-import { render } from '@testing-library/vue';
+import { render, fireEvent } from '@testing-library/vue';
 import N8nMarkdown from '../Markdown.vue';
 
 describe('components', () => {
@@ -15,6 +15,7 @@ describe('components', () => {
 				expect(checkbox).not.toBeChecked();
 			});
 		});
+
 		it('should render checked checkboxes', () => {
 			const wrapper = render(N8nMarkdown, {
 				props: {
@@ -27,6 +28,26 @@ describe('components', () => {
 				expect(checkbox).toBeChecked();
 			});
 		});
+
+		it('should toggle checkboxes when clicked', async () => {
+			const wrapper = render(N8nMarkdown, {
+				props: {
+					content: '__TODO__\n- [ ] Buy milk\n- [ ] Buy socks\n',
+				},
+			});
+			const checkboxes = wrapper.getAllByRole('checkbox');
+			expect(checkboxes).toHaveLength(2);
+			expect(checkboxes[0]).not.toBeChecked();
+			expect(checkboxes[1]).not.toBeChecked();
+
+			await fireEvent.click(checkboxes[0]);
+			expect(checkboxes[0]).toBeChecked();
+			expect(checkboxes[1]).not.toBeChecked();
+
+			const updatedContent = wrapper.emitted()['update-content'][0];
+			expect(updatedContent).toEqual(['__TODO__\n- [x] Buy milk\n- [ ] Buy socks\n']);
+		});
+
 		it('should render inputs as plain text', () => {
 			const wrapper = render(N8nMarkdown, {
 				props: {
diff --git a/packages/design-system/src/components/N8nSticky/Sticky.vue b/packages/design-system/src/components/N8nSticky/Sticky.vue
index 7e57612f52..f037f165bd 100644
--- a/packages/design-system/src/components/N8nSticky/Sticky.vue
+++ b/packages/design-system/src/components/N8nSticky/Sticky.vue
@@ -27,6 +27,7 @@
 					:content="modelValue"
 					:with-multi-breaks="true"
 					@markdown-click="onMarkdownClick"
+					@update-content="onUpdateModelValue"
 				/>
 			</div>
 			<div
diff --git a/packages/design-system/src/utils/__tests__/markdown.spec.ts b/packages/design-system/src/utils/__tests__/markdown.spec.ts
new file mode 100644
index 0000000000..c712b94048
--- /dev/null
+++ b/packages/design-system/src/utils/__tests__/markdown.spec.ts
@@ -0,0 +1,27 @@
+import { toggleCheckbox } from '../markdown';
+
+describe('toggleCheckbox', () => {
+	it('should do nothing when there are no checkboxes', () => {
+		const content = '"## I\'m a note \n Test\n"';
+		expect(toggleCheckbox(content, 0)).toBe(content);
+	});
+
+	it('should toggle a checkbox at a specific index', () => {
+		const content = '"## I\'m a note \n* [ ] First\n* [ ] Second\n* [ ] Third\n"';
+		expect(toggleCheckbox(content, 0)).toBe(
+			'"## I\'m a note \n* [x] First\n* [ ] Second\n* [ ] Third\n"',
+		);
+		expect(toggleCheckbox(content, 1)).toBe(
+			'"## I\'m a note \n* [ ] First\n* [x] Second\n* [ ] Third\n"',
+		);
+		expect(toggleCheckbox(content, 2)).toBe(
+			'"## I\'m a note \n* [ ] First\n* [ ] Second\n* [x] Third\n"',
+		);
+
+		const updatedContent = toggleCheckbox(content, 1);
+		expect(toggleCheckbox(updatedContent, 0)).toBe(
+			'"## I\'m a note \n* [x] First\n* [x] Second\n* [ ] Third\n"',
+		);
+		expect(toggleCheckbox(updatedContent, 1)).toBe(content);
+	});
+});
diff --git a/packages/design-system/src/utils/markdown.ts b/packages/design-system/src/utils/markdown.ts
index 919adcb62b..018659cc06 100644
--- a/packages/design-system/src/utils/markdown.ts
+++ b/packages/design-system/src/utils/markdown.ts
@@ -11,3 +11,36 @@ export const escapeMarkdown = (html: string | undefined): string => {
 
 	return withQuotes;
 };
+
+const checkedRegEx = /(\*|-) \[x\]/;
+const uncheckedRegEx = /(\*|-) \[\s\]/;
+
+/**
+ * Toggles the checkbox at the specified index in the given markdown string.
+ *
+ * @param markdown - The markdown string containing checkboxes.
+ * @param index - The index of the checkbox to toggle.
+ * @returns The updated markdown string with the checkbox toggled.
+ */
+export const toggleCheckbox = (markdown: string, index: number) => {
+	let cursor = 0;
+	const lines = markdown.split('\n');
+
+	for (let lineNumber = 0; lineNumber < lines.length; lineNumber++) {
+		const line = lines[lineNumber];
+		const checked = checkedRegEx.test(line);
+		const unchecked = uncheckedRegEx.test(line);
+
+		if (checked || unchecked) {
+			if (cursor === index) {
+				const regExp = checked ? checkedRegEx : uncheckedRegEx;
+				const replacement = checked ? '[ ]' : '[x]';
+				lines[lineNumber] = line.replace(regExp, `$1 ${replacement}`);
+				break;
+			}
+			cursor++;
+		}
+	}
+
+	return lines.join('\n');
+};