diff --git a/addons/web_editor/static/src/js/editor/odoo-editor/src/OdooEditor.js b/addons/web_editor/static/src/js/editor/odoo-editor/src/OdooEditor.js
index aa4505abe43..1d6cc50cd42 100644
--- a/addons/web_editor/static/src/js/editor/odoo-editor/src/OdooEditor.js
+++ b/addons/web_editor/static/src/js/editor/odoo-editor/src/OdooEditor.js
@@ -73,6 +73,7 @@ import {
     cleanZWS,
     isZWS,
     getDeepestPosition,
+    leftPos,
 } from './utils/utils.js';
 import { editorCommands } from './commands/commands.js';
 import { Powerbox } from './powerbox/Powerbox.js';
@@ -4282,15 +4283,27 @@ export class OdooEditor extends EventTarget {
         const odooEditorHtml = ev.clipboardData.getData('text/odoo-editor');
         const clipboardHtml = ev.clipboardData.getData('text/html');
         const targetSupportsHtmlContent = isHtmlContentSupported(sel.anchorNode);
+        // Replace entire link if its label is fully selected.
+        const link = closestElement(sel.anchorNode, 'a');
+        if (link && sel.toString().replace(/\u200B/g, '') === link.innerText.replace(/\u200B/g, '')) {
+            const start = leftPos(link);
+            // Exit link isolation since we're removing the link and editing outside of it.
+            if (this._fixLinkMutatedElements && this._fixLinkMutatedElements.link === link) {
+                this.resetContenteditableLink();
+                this._activateContenteditable();
+            }
+            link.remove();
+            setSelection(...start, ...start, false);
+        }
         if (odooEditorHtml && targetSupportsHtmlContent) {
             const fragment = parseHTML(odooEditorHtml);
             DOMPurify.sanitize(fragment, { IN_PLACE: true });
             if (fragment.hasChildNodes()) {
-                this.execCommand('insert', fragment);
+                this._applyCommand('insert', fragment);
             }
         } else if (files.length && targetSupportsHtmlContent) {
             this.addImagesFiles(files).then(html => {
-                const imageNodes = this.execCommand('insert', this._prepareClipboardData(html));
+                const imageNodes = this._applyCommand('insert', this._prepareClipboardData(html));
                 if (imageNodes && this.options.dropImageAsAttachment) {
                     // Mark images as having to be saved as attachments.
                     for (const imageNode of imageNodes) {
@@ -4299,7 +4312,7 @@ export class OdooEditor extends EventTarget {
                 }
             });
         } else if (clipboardHtml && targetSupportsHtmlContent) {
-            this.execCommand('insert', this._prepareClipboardData(clipboardHtml));
+            this._applyCommand('insert', this._prepareClipboardData(clipboardHtml));
         } else {
             const text = ev.clipboardData.getData('text/plain');
             const selectionIsInsideALink = !!closestElement(sel.anchorNode, 'a');
@@ -4326,13 +4339,19 @@ export class OdooEditor extends EventTarget {
                     }
                 } else if (isImageUrl || youtubeUrl) {
                     // Open powerbox with commands to embed media or paste as link.
-                    // Insert URL as text, store history step index to revert it later.
+                    // Store history step index to revert it later.
                     const stepIndexBeforeInsert = this._historySteps.length - 1;
+                    // Store mutations before text insertion, to reapply them after history revert.
+                    this.observerFlush();
+                    const currentStepMutations = [...this._currentStep.mutations];
+                    // Insert URL as text, revert it later.
                     this._applyCommand('insert', text);
                     const revertTextInsertion = () => {
                         this.historyRevertUntil(stepIndexBeforeInsert);
                         this.historyStep(true);
                         this._historyStepsStates.set(peek(this._historySteps).id, 'consumed');
+                        // Reapply mutations that were done before the text insertion.
+                        this.historyApply(currentStepMutations);
                     };
                     let commands;
                     const pasteAsURLCommand = {
diff --git a/addons/web_editor/static/src/js/editor/odoo-editor/test/spec/copyPaste.test.js b/addons/web_editor/static/src/js/editor/odoo-editor/test/spec/copyPaste.test.js
index 74ddaf0bd30..3dbd4c189e9 100644
--- a/addons/web_editor/static/src/js/editor/odoo-editor/test/spec/copyPaste.test.js
+++ b/addons/web_editor/static/src/js/editor/odoo-editor/test/spec/copyPaste.test.js
@@ -1418,13 +1418,76 @@ describe('Paste', () => {
                     contentAfter: '<p>a<a href="https://boom.com">boom[].com</a>d</p>',
                 });
             });
-            it('should paste and transform URL over the existing url', async () => {
+            it('should replace link for new content when pasting in an empty link', async () => {
                 await testEditor(BasicEditor, {
-                    contentBefore: '<p>ab[<a href="http://www.xyz.com">http://www.xyz.com</a>]cd</p>',
+                    contentBefore: '<p><a href="#" oe-zws-empty-inline="">[]\u200B</a></p>',
                     stepFunction: async editor => {
-                        await pasteText(editor, 'https://www.xyz.xdc ');
+                        await pasteText(editor, 'abc');
                     },
-                    contentAfter: '<p>ab<a href="https://www.xyz.xdc">https://www.xyz.xdc</a> []cd</p>',
+                    contentAfter: '<p>abc[]</p>',
+                });
+                await testEditor(BasicEditor, {
+                    contentBefore: '<p>xy<a href="#" oe-zws-empty-inline="">\u200B[]</a>z</p>',
+                    stepFunction: async editor => {
+                        await pasteText(editor, 'abc');
+                    },
+                    contentAfter: '<p>xyabc[]z</p>',
+                });
+                await testEditor(BasicEditor, {
+                    contentBefore: '<p>xy<a href="#" oe-zws-empty-inline="">\u200B[]</a>z</p>',
+                    stepFunction: async editor => {
+                        await pasteText(editor, 'http://odoo.com');
+                    },
+                    contentAfter: '<p>xy<a href="http://odoo.com">http://odoo.com</a>[]z</p>',
+                });
+                const imageUrl = 'https://download.odoocdn.com/icons/website/static/description/icon.png';
+                await testEditor(BasicEditor, {
+                    contentBefore: '<p>xy<a href="#" oe-zws-empty-inline="">\u200B[]</a>z</p>',
+                    stepFunction: async editor => {
+                        await pasteText(editor, imageUrl);
+                        // Ensure the powerbox is active
+                        window.chai.expect(editor.powerbox.isOpen).to.be.true;
+                        // Pick the first command (Embed image)
+                        triggerEvent(editor.editable, 'keydown', { key: 'Enter' });
+                    },
+                    contentAfter: `<p>xy<img src="${imageUrl}">[]z</p>`,
+                });
+                await testEditor(BasicEditor, {
+                    contentBefore: '<p>xy<a href="#" oe-zws-empty-inline="">\u200B[]</a>z</p>',
+                    stepFunction: async editor => {
+                        await pasteText(editor, imageUrl);
+                        // Ensure the powerbox is active
+                        window.chai.expect(editor.powerbox.isOpen).to.be.true;
+                        // Pick the second command (Paste as URL)
+                        triggerEvent(editor.editable, 'keydown', { key: 'ArrowDown' });
+                        triggerEvent(editor.editable, 'keydown', { key: 'Enter' });
+                    },
+                    contentAfter: `<p>xy<a href="${imageUrl}">${imageUrl}</a>[]z</p>`,
+                });
+            });
+            it('should paste and transform plain text content over an empty link', async () => {
+                await testEditor(BasicEditor, {
+                    contentBefore: '<p><a href="#">[]\u200B</a></p>',
+                    stepFunction: async editor => {
+                        await pasteText(editor, 'abc www.odoo.com xyz');
+                    },
+                    contentAfter: '<p>abc <a href="https://www.odoo.com">www.odoo.com</a> xyz[]</p>',
+                });
+                await testEditor(BasicEditor, {
+                    contentBefore: '<p><a href="#">[]\u200B</a></p>',
+                    stepFunction: async editor => {
+                        await pasteText(editor, 'odoo.com\ngoogle.com');
+                    },
+                    contentAfter: '<p><a href="https://odoo.com">odoo.com</a><br><a href="https://google.com">google.com</a>[]<br></p>',
+                });
+            });
+            it('should paste html content over an empty link', async () => {
+                await testEditor(BasicEditor, {
+                    contentBefore: '<p><a href="#">[]\u200B</a></p>',
+                    stepFunction: async editor => {
+                        await pasteHtml(editor, '<a href="www.odoo.com">odoo.com</a><br><a href="www.google.com">google.com</a>');
+                    },
+                    contentAfter: '<p><a href="www.odoo.com">odoo.com</a><br><a href="www.google.com">google.com</a>[]</p>',
                 });
             });
             it('should paste and transform URL among text', async () => {
@@ -1536,7 +1599,6 @@ describe('Paste', () => {
                     },
                     contentAfter: '<p>[abc]</p>',
                 });
- 
             });
             it('should restore selection after pasting HTML followed by UNDO', async () => {
                 await testEditor(BasicEditor, {
@@ -1589,6 +1651,73 @@ describe('Paste', () => {
                     contentAfter: `<p><a href="${url}">${url}</a> <a href="${videoUrl}">${videoUrl}</a> <a href="${imgUrl}">${imgUrl}</a>[]<br></p>`,
                 });
             });
+            it('should paste and transform URL over the existing url', async () => {
+                await testEditor(BasicEditor, {
+                    contentBefore: '<p>ab[<a href="http://www.xyz.com">http://www.xyz.com</a>]cd</p>',
+                    stepFunction: async editor => {
+                        await pasteText(editor, 'https://www.xyz.xdc ');
+                    },
+                    contentAfter: '<p>ab<a href="https://www.xyz.xdc">https://www.xyz.xdc</a> []cd</p>',
+                });
+            });
+            it('should paste plain text content over a link if all of its contents is selected', async () => {
+                await testEditor(BasicEditor, {
+                    contentBefore: '<p>a<a href="#">[xyz]</a>d</p>',
+                    stepFunction: async editor => {
+                        await pasteText(editor, 'bc');
+                    },
+                    contentAfter: '<p>abc[]d</p>',
+                });
+            });
+            it('should paste and transform plain text content over a link if all of its contents is selected', async () => {
+                await testEditor(BasicEditor, {
+                    contentBefore: '<p><a href="#">[xyz]</a></p>',
+                    stepFunction: async editor => {
+                        await pasteText(editor, 'www.odoo.com');
+                    },
+                    contentAfter: '<p><a href="https://www.odoo.com">www.odoo.com</a>[]</p>',
+                });
+                await testEditor(BasicEditor, {
+                    contentBefore: '<p><a href="#">[xyz]</a></p>',
+                    stepFunction: async editor => {
+                        await pasteText(editor, 'abc www.odoo.com xyz');
+                    },
+                    contentAfter: '<p>abc <a href="https://www.odoo.com">www.odoo.com</a> xyz[]</p>',
+                });
+                const imageUrl = 'https://download.odoocdn.com/icons/website/static/description/icon.png';
+                await testEditor(BasicEditor, {
+                    contentBefore: '<p>ab<a href="http://www.xyz.com">[http://www.xyz.com]</a>cd</p>',
+                    stepFunction: async editor => {
+                        await pasteText(editor, imageUrl);
+                        // Ensure the powerbox is active
+                        window.chai.expect(editor.powerbox.isOpen).to.be.true;
+                        // Pick the first command (Embed image)
+                        triggerEvent(editor.editable, 'keydown', { key: 'Enter' });
+                    },
+                    contentAfter: `<p>ab<img src="${imageUrl}">[]cd</p>`,
+                });
+                await testEditor(BasicEditor, {
+                    contentBefore: '<p>ab<a href="http://www.xyz.com">[http://www.xyz.com]</a>cd</p>',
+                    stepFunction: async editor => {
+                        await pasteText(editor, imageUrl);
+                        // Ensure the powerbox is active
+                        window.chai.expect(editor.powerbox.isOpen).to.be.true;
+                        // Pick the second command (Paste as URL)
+                        triggerEvent(editor.editable, 'keydown', { key: 'ArrowDown' });
+                        triggerEvent(editor.editable, 'keydown', { key: 'Enter' });
+                    },
+                    contentAfter: `<p>ab<a href="${imageUrl}">${imageUrl}</a>[]cd</p>`,
+                });
+            });
+            it('should paste html content over a link if all of its contents is selected', async () => {
+                await testEditor(BasicEditor, {
+                    contentBefore: '<p><a href="#">[xyz]</a></p>',
+                    stepFunction: async editor => {
+                        await pasteHtml(editor, '<a href="www.odoo.com">odoo.com</a><br><a href="www.google.com">google.com</a>');
+                    },
+                    contentAfter: '<p><a href="www.odoo.com">odoo.com</a><br><a href="www.google.com">google.com</a>[]</p>',
+                });
+            });
         });
     });
     describe('images', () => {