diff --git a/demos/src/Examples/AutolinkValidation/React/index.jsx b/demos/src/Examples/AutolinkValidation/React/index.jsx
index 21e28c44..b32b9ecf 100644
--- a/demos/src/Examples/AutolinkValidation/React/index.jsx
+++ b/demos/src/Examples/AutolinkValidation/React/index.jsx
@@ -23,8 +23,48 @@ export default () => {
     },
   })
 
+  const setLink = React.useCallback(() => {
+    const previousUrl = editor.getAttributes('link').href
+    const url = window.prompt('URL', previousUrl)
+
+    // cancelled
+    if (url === null) {
+      return
+    }
+
+    // empty
+    if (url === '') {
+      editor.chain().focus().extendMarkRange('link').unsetLink()
+        .run()
+
+      return
+    }
+
+    // update link
+    editor.chain().focus().extendMarkRange('link').setLink({ href: url })
+      .run()
+  }, [editor])
+
+  if (!editor) {
+    return null
+  }
+
   return (
     <div>
+      <button
+        onClick={setLink}
+        className={editor.isActive('link') ? 'is-active' : ''}
+        data-testid="setLink"
+      >
+        setLink
+      </button>
+      <button
+        onClick={() => editor.chain().focus().unsetLink().run()}
+        disabled={!editor.isActive('link')}
+        data-testid="unsetLink"
+      >
+        unsetLink
+      </button>
       <EditorContent editor={editor} />
     </div>
   )
diff --git a/demos/src/Examples/AutolinkValidation/React/index.spec.js b/demos/src/Examples/AutolinkValidation/React/index.spec.js
index e1d6b7d1..0967daba 100644
--- a/demos/src/Examples/AutolinkValidation/React/index.spec.js
+++ b/demos/src/Examples/AutolinkValidation/React/index.spec.js
@@ -8,25 +8,30 @@ context('/src/Examples/AutolinkValidation/React/', () => {
   })
 
   const validLinks = [
-    'https://tiptap.dev',
-    'http://tiptap.dev',
-    'https://www.tiptap.dev/',
-    'http://www.tiptap.dev/',
+    // [rawTextInput, textThatShouldBeLinked]
+    ['https://tiptap.dev ', 'https://tiptap.dev'],
+    ['http://tiptap.dev ', 'http://tiptap.dev'],
+    ['https://www.tiptap.dev/ ', 'https://www.tiptap.dev/'],
+    ['http://www.tiptap.dev/ ', 'http://www.tiptap.dev/'],
+    ['[http://www.example.com/] ', 'http://www.example.com/'],
+    ['(http://www.example.com/) ', 'http://www.example.com/'],
   ]
 
   const invalidLinks = [
     'tiptap.dev',
     'www.tiptap.dev',
+    // If you don't type a space, don't autolink
+    'https://tiptap.dev',
   ]
 
   validLinks.forEach(link => {
-    it(`${link} should get autolinked`, () => {
-      cy.get('.ProseMirror').type(link)
-      cy.get('.ProseMirror').should('have.text', link)
+    it(`${link[0]} should get autolinked`, () => {
+      cy.get('.ProseMirror').type(link[0])
+      cy.get('.ProseMirror').should('have.text', link[0])
       cy.get('.ProseMirror')
         .find('a')
         .should('have.length', 1)
-        .should('have.attr', 'href', link)
+        .should('have.attr', 'href', link[1])
     })
   })
 
@@ -39,4 +44,66 @@ context('/src/Examples/AutolinkValidation/React/', () => {
         .should('have.length', 0)
     })
   })
+
+  it('should not relink unset links after entering second link', () => {
+    cy.get('.ProseMirror').type('https://tiptap.dev {home}')
+    cy.get('.ProseMirror').should('have.text', 'https://tiptap.dev ')
+    cy.get('[data-testid=unsetLink]').click()
+    cy.get('.ProseMirror')
+      .find('a')
+      .should('have.length', 0)
+    cy.get('.ProseMirror').type('{end}http://www.example.com/ ')
+    cy.get('.ProseMirror')
+      .find('a')
+      .should('have.length', 1)
+      .should('have.attr', 'href', 'http://www.example.com/')
+  })
+
+  it('should not relink unset links after hitting next paragraph', () => {
+    cy.get('.ProseMirror').type('https://tiptap.dev {home}')
+    cy.get('.ProseMirror').should('have.text', 'https://tiptap.dev ')
+    cy.get('[data-testid=unsetLink]').click()
+    cy.get('.ProseMirror')
+      .find('a')
+      .should('have.length', 0)
+    cy.get('.ProseMirror').type('{end}typing other text should prevent the link from relinking when hitting enter{enter}')
+    cy.get('.ProseMirror')
+      .find('a')
+      .should('have.length', 0)
+  })
+
+  it('should not relink unset links after modifying', () => {
+    cy.get('.ProseMirror').type('https://tiptap.dev {home}')
+    cy.get('.ProseMirror').should('have.text', 'https://tiptap.dev ')
+    cy.get('[data-testid=unsetLink]').click()
+    cy.get('.ProseMirror')
+      .find('a')
+      .should('have.length', 0)
+    cy.get('.ProseMirror')
+      .type('{home}')
+      .type('{rightArrow}'.repeat('https://'.length))
+      .type('blah')
+    cy.get('.ProseMirror').should('have.text', 'https://blahtiptap.dev ')
+    cy.get('.ProseMirror')
+      .find('a')
+      .should('have.length', 0)
+  })
+
+  it('should autolink after hitting enter (new paragraph)', () => {
+    cy.get('.ProseMirror').type('https://tiptap.dev{enter}')
+    cy.get('.ProseMirror').should('have.text', 'https://tiptap.dev')
+    cy.get('.ProseMirror')
+      .find('a')
+      .should('have.length', 1)
+      .should('have.attr', 'href', 'https://tiptap.dev')
+  })
+
+  it('should autolink after hitting shift-enter (hardbreak)', () => {
+    cy.get('.ProseMirror').type('https://tiptap.dev{shift+enter}')
+    cy.get('.ProseMirror').should('have.text', 'https://tiptap.dev')
+    cy.get('.ProseMirror')
+      .find('a')
+      .should('have.length', 1)
+      .should('have.attr', 'href', 'https://tiptap.dev')
+  })
 })
diff --git a/demos/src/Examples/AutolinkValidation/Vue/index.spec.js b/demos/src/Examples/AutolinkValidation/Vue/index.spec.js
index a7496597..c08e2df5 100644
--- a/demos/src/Examples/AutolinkValidation/Vue/index.spec.js
+++ b/demos/src/Examples/AutolinkValidation/Vue/index.spec.js
@@ -8,25 +8,30 @@ context('/src/Examples/AutolinkValidation/Vue/', () => {
   })
 
   const validLinks = [
-    'https://tiptap.dev',
-    'http://tiptap.dev',
-    'https://www.tiptap.dev/',
-    'http://www.tiptap.dev/',
+    // [rawTextInput, textThatShouldBeLinked]
+    ['https://tiptap.dev ', 'https://tiptap.dev'],
+    ['http://tiptap.dev ', 'http://tiptap.dev'],
+    ['https://www.tiptap.dev/ ', 'https://www.tiptap.dev/'],
+    ['http://www.tiptap.dev/ ', 'http://www.tiptap.dev/'],
+    ['[http://www.example.com/] ', 'http://www.example.com/'],
+    ['(http://www.example.com/) ', 'http://www.example.com/'],
   ]
 
   const invalidLinks = [
     'tiptap.dev',
     'www.tiptap.dev',
+    // If you don't type a space, don't autolink
+    'https://tiptap.dev',
   ]
 
   validLinks.forEach(link => {
-    it(`${link} should get autolinked`, () => {
-      cy.get('.ProseMirror').type(link)
-      cy.get('.ProseMirror').should('have.text', link)
+    it(`${link[0]} should get autolinked`, () => {
+      cy.get('.ProseMirror').type(link[0])
+      cy.get('.ProseMirror').should('have.text', link[0])
       cy.get('.ProseMirror')
         .find('a')
         .should('have.length', 1)
-        .should('have.attr', 'href', link)
+        .should('have.attr', 'href', link[1])
     })
   })
 
diff --git a/packages/extension-link/src/helpers/autolink.ts b/packages/extension-link/src/helpers/autolink.ts
index a6dcb55b..ae59c3f8 100644
--- a/packages/extension-link/src/helpers/autolink.ts
+++ b/packages/extension-link/src/helpers/autolink.ts
@@ -3,6 +3,7 @@ import {
   findChildrenInRange,
   getChangedRanges,
   getMarksBetween,
+  NodeWithPos,
 } from '@tiptap/core'
 import { find, test } from 'linkifyjs'
 import { MarkType } from 'prosemirror-model'
@@ -58,46 +59,59 @@ export function autolink(options: AutolinkOptions): Plugin {
           })
 
         // now let’s see if we can add new links
-        findChildrenInRange(newState.doc, newRange, node => node.isTextblock)
-          .forEach(textBlock => {
-            // we need to define a placeholder for leaf nodes
-            // so that the link position can be calculated correctly
-            const text = newState.doc.textBetween(
-              textBlock.pos,
-              textBlock.pos + textBlock.node.nodeSize,
-              undefined,
-              ' ',
-            )
+        const nodesInChangedRanges = findChildrenInRange(newState.doc, newRange, node => node.isTextblock)
 
-            find(text)
-              .filter(link => link.isLink)
-              .filter(link => {
-                if (options.validate) {
-                  return options.validate(link.value)
-                }
+        let textBlock: NodeWithPos | undefined
+        let textBeforeWhitespace: string | undefined
 
-                return true
-              })
-              // calculate link position
-              .map(link => ({
-                ...link,
-                from: textBlock.pos + link.start + 1,
-                to: textBlock.pos + link.end + 1,
+        if (nodesInChangedRanges.length > 1) {
+          // Grab the first node within the changed ranges (ex. the first of two paragraphs when hitting enter)
+          textBlock = nodesInChangedRanges[0]
+          textBeforeWhitespace = newState.doc.textBetween(
+            textBlock.pos,
+            textBlock.pos + textBlock.node.nodeSize,
+            undefined,
+            ' ',
+          )
+        } else if (
+          // We want to make sure to include the block seperator argument to treat hard breaks like spaces
+          newState.doc.textBetween(newRange.from, newRange.to, ' ', ' ').endsWith(' ')
+        ) {
+          textBlock = nodesInChangedRanges[0]
+          textBeforeWhitespace = newState.doc.textBetween(
+            textBlock.pos,
+            newRange.to,
+            undefined,
+            ' ',
+          )
+        }
+
+        if (textBlock && textBeforeWhitespace) {
+          const wordsBeforeWhitespace = textBeforeWhitespace.split(' ').filter(s => s !== '')
+          const lastWordBeforeSpace = wordsBeforeWhitespace[wordsBeforeWhitespace.length - 1]
+          const lastWordAndBlockOffset = textBlock.pos + textBeforeWhitespace.lastIndexOf(lastWordBeforeSpace)
+
+          find(lastWordBeforeSpace)
+            .filter(link => link.isLink)
+            .filter(link => {
+              if (options.validate) {
+                return options.validate(link.value)
+              }
+              return true
+            })
+            // calculate link position
+            .map(link => ({
+              ...link,
+              from: lastWordAndBlockOffset + link.start + 1,
+              to: lastWordAndBlockOffset + link.end + 1,
+            }))
+            // add link mark
+            .forEach(link => {
+              tr.addMark(link.from, link.to, options.type.create({
+                href: link.href,
               }))
-              // check if link is within the changed range
-              .filter(link => {
-                const fromIsInRange = newRange.from >= link.from && newRange.from <= link.to
-                const toIsInRange = newRange.to >= link.from && newRange.to <= link.to
-
-                return fromIsInRange || toIsInRange
-              })
-              // add link mark
-              .forEach(link => {
-                tr.addMark(link.from, link.to, options.type.create({
-                  href: link.href,
-                }))
-              })
-          })
+            })
+        }
       })
 
       if (!tr.steps.length) {