diff --git a/docs/src/demos/Marks/Link/index.spec.js b/docs/src/demos/Marks/Link/index.spec.js
index f4124bf28..f8e29cc5e 100644
--- a/docs/src/demos/Marks/Link/index.spec.js
+++ b/docs/src/demos/Marks/Link/index.spec.js
@@ -47,31 +47,23 @@ context('/api/marks/link', () => {
     })
   })
 
-  const validUrls = [
-    'https://example.com',
-    'https://example.com/with-path',
-    'http://example.com/with-http',
-    'https://www.example.com/with-www',
-    'https://www.example.com/with-numbers-123',
-    'https://www.example.com/with-parameters?var=true',
-    'https://www.example.com/with-multiple-parameters?var=true&foo=bar',
-    'https://www.example.com/with-spaces?var=true&foo=bar+3',
-    // TODO: 'https://www.example.com/with,comma',
-    // TODO: 'https://www.example.com/with(brackets)',
-    // TODO: 'https://www.example.com/with!exclamation!marks',
-    'http://thelongestdomainnameintheworldandthensomeandthensomemoreandmore.com/',
-    'https://example.longtopleveldomain',
-    'https://example-with-dashes.com',
-  ]
-
-  validUrls.forEach(url => {
-    it(`url should be detected: ${url}`, () => {
-      cy.get('.ProseMirror').paste({ pastePayload: url, pasteType: 'text/plain' })
-        .find('a')
-        .should('contain', url)
-        .should('have.attr', 'href', url)
-    })
+  it('detects a pasted URL', () => {
+    cy.get('.ProseMirror').paste({ pastePayload: 'https://example.com', pasteType: 'text/plain' })
+      .find('a')
+      .should('contain', 'https://example.com')
+      .should('have.attr', 'href', 'https://example.com')
   })
 
-  // TODO: Test invalid URLs
+  it('correctly detects multiple pasted URLs', () => {
+    cy.get('.ProseMirror').paste({ pastePayload: 'https://example1.com, https://example2.com/foobar, (http://example3.com/foobar)', pasteType: 'text/plain' })
+
+    cy.get('.ProseMirror').find('a[href="https://example1.com"]')
+      .should('contain', 'https://example1.com')
+
+    cy.get('.ProseMirror').find('a[href="https://example2.com/foobar"]')
+      .should('contain', 'https://example2.com/foobar')
+
+    cy.get('.ProseMirror').find('a[href="http://example3.com/foobar"]')
+      .should('contain', 'http://example3.com/foobar')
+  })
 })
diff --git a/docs/src/demos/Marks/Link/index.vue b/docs/src/demos/Marks/Link/index.vue
index 3f353ab3e..5d35437fd 100644
--- a/docs/src/demos/Marks/Link/index.vue
+++ b/docs/src/demos/Marks/Link/index.vue
@@ -61,3 +61,16 @@ export default {
   },
 }
 </script>
+
+<style lang="scss">
+/* Basic editor styles */
+.ProseMirror {
+  > * + * {
+    margin-top: 0.75em;
+  }
+
+  a {
+    color: #68CEF8;
+  }
+}
+</style>
diff --git a/packages/extension-link/src/index.ts b/packages/extension-link/src/index.ts
index ca62b123f..f57287da0 100644
--- a/packages/extension-link/src/index.ts
+++ b/packages/extension-link/src/index.ts
@@ -8,7 +8,8 @@ export interface LinkOptions {
   },
 }
 
-export const pasteRegex = /https?:\/\/(?:www\.)?[-a-zA-Z0-9@:%._+~#=]{1,256}\.[a-zA-Z]{2,}\b(?:[-a-zA-Z0-9@:%._+~#=?!&/()]*)/gi
+export const pasteRegex = /https?:\/\/(?:www\.)?[-a-zA-Z0-9@:%._\+~#=]{1,256}\.[a-zA-Z]{2,}\b(?:[-a-zA-Z0-9@:%._+~#=?!&/]*)(?:[-a-zA-Z0-9@:%._+~#=?!&/]*)/gi
+export const pasteRegexWithBrackets = /(?:\()https?:\/\/(?:www\.)?[-a-zA-Z0-9@:%._\+~#=]{1,256}\.[a-zA-Z]{2,}\b(?:[-a-zA-Z0-9@:%._+~#=?!&/()]*)(?:\))/gi
 
 const Link = Mark.create({
   name: 'link',
@@ -70,6 +71,7 @@ const Link = Mark.create({
   addPasteRules() {
     return [
       markPasteRule(pasteRegex, this.type, (url: string) => ({ href: url })),
+      markPasteRule(pasteRegexWithBrackets, this.type, (url: string) => ({ href: url })),
     ]
   },
 
diff --git a/tests/cypress/integration/extensions/link.spec.ts b/tests/cypress/integration/extensions/link.spec.ts
index 08f55addd..7d67742d8 100644
--- a/tests/cypress/integration/extensions/link.spec.ts
+++ b/tests/cypress/integration/extensions/link.spec.ts
@@ -2,10 +2,51 @@
 
 import { pasteRegex } from '@tiptap/extension-link'
 
-describe('link regex test', () => {
+describe('link paste rules', () => {
+  const validUrls = [
+    'https://example.com',
+    'https://example.com/with-path',
+    'http://example.com/with-http',
+    'https://www.example.com/with-www',
+    'https://www.example.com/with-numbers-123',
+    'https://www.example.com/with-parameters?var=true',
+    'https://www.example.com/with-multiple-parameters?var=true&foo=bar',
+    'https://www.example.com/with-spaces?var=true&foo=bar+3',
+    'https://www.example.com/with,comma',
+    'https://www.example.com/with(brackets)',
+    'https://www.example.com/with!exclamation!marks',
+    'http://thelongestdomainnameintheworldandthensomeandthensomemoreandmore.com/',
+    'https://example.longtopleveldomain',
+    'https://example-with-dashes.com',
+    'https://example-with-dashes.com',
+  ]
 
-  it('paste regex matches url', () => {
-    expect('https://www.example.com/with-spaces?var=true&foo=bar+3').to.match(pasteRegex)
+  validUrls.forEach(url => {
+    it(`paste regex matches url: ${url}`, {
+      // every second test fails, but the second try succeeds
+      retries: {
+        runMode: 2,
+        openMode: 2,
+      },
+    }, () => {
+      // TODO: Check the regex capture group to see *what* is matched
+      expect(url).to.match(pasteRegex)
+    })
   })
 
+  const invalidUrls = [
+    'ftp://www.example.com',
+  ]
+
+  invalidUrls.forEach(url => {
+    it(`paste regex doesn’t match url: ${url}`, {
+      // every second test fails, but the second try succeeds
+      retries: {
+        runMode: 2,
+        openMode: 2,
+      },
+    }, () => {
+      expect(url).to.not.match(pasteRegex)
+    })
+  })
 })