diff --git a/cypress/integration/taskLists.spec.ts b/cypress/integration/taskLists.spec.ts
new file mode 100644
index 000000000..8f6b2a922
--- /dev/null
+++ b/cypress/integration/taskLists.spec.ts
@@ -0,0 +1,87 @@
+/*
+ * SPDX-FileCopyrightText: 2021 The HedgeDoc developers (see AUTHORS file)
+ *
+ * SPDX-License-Identifier: AGPL-3.0-only
+ */
+
+const TEST_STRING_UNCHECKED = '- [ ] abc\n\n* [ ] abc\n\n+ [ ] abc\n\n1. [ ] abc\n\n10. [ ] abc\n\n5) [ ] abc'
+const TEST_STRING_CHECKED_LOWER = '- [x] abc\n\n* [x] abc\n\n+ [x] abc\n\n1. [x] abc\n\n10. [x] abc\n\n5) [x] abc'
+const TEST_STRING_CHECKED_UPPER = '- [X] abc\n\n* [X] abc\n\n+ [X] abc\n\n1. [X] abc\n\n10. [X] abc\n\n5) [X] abc'
+const TEST_STRING_INVALID = '- [Y] abc\n\n* [  ] abc\n\n+ [-] abc\n\n1. [.] abc\n\n10. [] abc\n\n5) [-] abc'
+
+describe('Task lists ', () => {
+  beforeEach(() => {
+    cy.visitTestEditor()
+  })
+
+  describe('render with checkboxes ', () => {
+    it('when unchecked', () => {
+      cy.codemirrorFill(TEST_STRING_UNCHECKED)
+      cy.getMarkdownBody()
+        .find('input[type=checkbox]')
+        .should('have.length', 6)
+    })
+
+    it('when checked lowercase', () => {
+      cy.codemirrorFill(TEST_STRING_CHECKED_LOWER)
+      cy.getMarkdownBody()
+        .find('input[type=checkbox]')
+        .should('have.length', 6)
+    })
+
+    it('when checked uppercase', () => {
+      cy.codemirrorFill(TEST_STRING_CHECKED_UPPER)
+      cy.getMarkdownBody()
+        .find('input[type=checkbox]')
+        .should('have.length', 6)
+    })
+  })
+
+  it('do not render as checkboxes when invalid', () => {
+    cy.codemirrorFill(TEST_STRING_INVALID)
+    cy.getMarkdownBody()
+      .find('input[type=checkbox]')
+      .should('have.length', 0)
+  })
+
+  describe('are clickable and change the markdown source ', () => {
+    it('from unchecked to checked', () => {
+      cy.codemirrorFill(TEST_STRING_UNCHECKED)
+      cy.getMarkdownBody()
+        .find('input[type=checkbox]')
+        .each(box => {
+          box.trigger('click')
+        })
+      cy.get('.CodeMirror-line > span')
+        .should('exist')
+        .should('contain.text', '[x]')
+        .should('not.contain.text', '[ ]')
+    })
+
+    it('from checked (lowercase) to unchecked', () => {
+      cy.codemirrorFill(TEST_STRING_CHECKED_LOWER)
+      cy.getMarkdownBody()
+        .find('input[type=checkbox]')
+        .each(box => {
+          box.trigger('click')
+        })
+      cy.get('.CodeMirror-line > span')
+        .should('exist')
+        .should('contain.text', '[ ]')
+        .should('not.contain.text', '[x]')
+    })
+
+    it('from checked (uppercase) to unchecked', () => {
+      cy.codemirrorFill(TEST_STRING_CHECKED_UPPER)
+      cy.getMarkdownBody()
+        .find('input[type=checkbox]')
+        .each(box => {
+          box.trigger('click')
+        })
+      cy.get('.CodeMirror-line > span')
+        .should('exist')
+        .should('contain.text', '[ ]')
+        .should('not.contain.text', '[X]')
+    })
+  })
+})
diff --git a/src/redux/note-details/reducers.ts b/src/redux/note-details/reducers.ts
index 93954cd42..73663bd1d 100644
--- a/src/redux/note-details/reducers.ts
+++ b/src/redux/note-details/reducers.ts
@@ -87,7 +87,7 @@ export const NoteDetailsReducer: Reducer<NoteDetails, NoteDetailsAction> = (stat
   }
 }
 
-const TASK_REGEX = /(\s*[-*] )(\[[ xX]])( .*)/
+const TASK_REGEX = /(\s*(?:[-*+]|\d+[.)]) )(\[[ xX]])( .*)/
 const setCheckboxInMarkdownContent = (markdownContent: string, lineInMarkdown: number, checked: boolean): string => {
   const lines = markdownContent.split('\n')
   const results = TASK_REGEX.exec(lines[lineInMarkdown])