diff --git a/addons/web_editor/static/lib/odoo-editor/src/OdooEditor.js b/addons/web_editor/static/lib/odoo-editor/src/OdooEditor.js
index 668b3a086f3..45c59b3faad 100644
--- a/addons/web_editor/static/lib/odoo-editor/src/OdooEditor.js
+++ b/addons/web_editor/static/lib/odoo-editor/src/OdooEditor.js
@@ -46,6 +46,7 @@ import {
     YOUTUBE_URL_GET_VIDEO_ID,
     unwrapContents,
     peek,
+    rightPos,
 } from './utils/utils.js';
 import { editorCommands } from './commands/commands.js';
 import { Powerbox } from './powerbox/Powerbox.js';
@@ -2138,7 +2139,21 @@ export class OdooEditor extends EventTarget {
                 this.historyRollback();
                 ev.preventDefault();
                 if (this._applyCommand('oEnter') === UNBREAKABLE_ROLLBACK_CODE) {
-                    this._applyCommand('oShiftEnter');
+                    const brs = this._applyCommand('oShiftEnter');
+                    const anchor = brs[0].parentElement;
+                    if (anchor.nodeName === 'A') {
+                        if (brs.includes(anchor.firstChild)) {
+                            brs.forEach(br => anchor.before(br));
+                            setSelection(...rightPos(brs[brs.length - 1]));
+                            this.sanitize();
+                            this.historyStep();
+                        } else if (brs.includes(anchor.lastChild)) {
+                            brs.forEach(br => anchor.after(br));
+                            setSelection(...rightPos(brs[0]));
+                            this.sanitize();
+                            this.historyStep();
+                        }
+                    }
                 }
             } else if (['insertText', 'insertCompositionText'].includes(ev.inputType)) {
                 // insertCompositionText, courtesy of Samsung keyboard.
diff --git a/addons/web_editor/static/lib/odoo-editor/src/commands/shiftEnter.js b/addons/web_editor/static/lib/odoo-editor/src/commands/shiftEnter.js
index 3b106e124f2..20c56ee8ec3 100644
--- a/addons/web_editor/static/lib/odoo-editor/src/commands/shiftEnter.js
+++ b/addons/web_editor/static/lib/odoo-editor/src/commands/shiftEnter.js
@@ -12,7 +12,7 @@ import {
 } from '../utils/utils.js';
 
 Text.prototype.oShiftEnter = function (offset) {
-    this.parentElement.oShiftEnter(splitTextNode(this, offset));
+    return this.parentElement.oShiftEnter(splitTextNode(this, offset));
 };
 
 HTMLElement.prototype.oShiftEnter = function (offset) {
@@ -39,4 +39,6 @@ HTMLElement.prototype.oShiftEnter = function (offset) {
             break;
         }
     }
+
+    return brEls;
 };
diff --git a/addons/web_editor/static/lib/odoo-editor/test/spec/collab.test.js b/addons/web_editor/static/lib/odoo-editor/test/spec/collab.test.js
index 7eed71df836..9dcd7b73e7a 100644
--- a/addons/web_editor/static/lib/odoo-editor/test/spec/collab.test.js
+++ b/addons/web_editor/static/lib/odoo-editor/test/spec/collab.test.js
@@ -139,7 +139,7 @@ const testMultiEditor = spec => {
                 clientInfo.editor.onExternalHistorySteps(missingSteps.concat([step]));
             },
         });
-        clientInfo.editor.keyboardType = 'PHYSICAL_KEYBOARD';
+        clientInfo.editor.keyboardType = 'PHYSICAL';
         const selection = selections[clientInfo.clientId];
         if (selection) {
             setTestSelection(selection, iframeDocument);
diff --git a/addons/web_editor/static/lib/odoo-editor/test/spec/editor.test.js b/addons/web_editor/static/lib/odoo-editor/test/spec/editor.test.js
index 66ac039f857..ab79496d972 100644
--- a/addons/web_editor/static/lib/odoo-editor/test/spec/editor.test.js
+++ b/addons/web_editor/static/lib/odoo-editor/test/spec/editor.test.js
@@ -2248,6 +2248,31 @@ X[]
                         contentAfter: '<p><b>abc</b></p><p>[]<br></p>',
                     });
                 });
+                it.only('should insert line breaks outside the edges of an anchor', async () => {
+                    const pressEnter = editor => {
+                        editor.document.execCommand('insertParagraph');
+                    }
+                    await testEditor(BasicEditor, {
+                        contentBefore: '<div>ab<a>[]cd</a></div>',
+                        stepFunction: pressEnter,
+                        contentAfter: '<div>ab<br><a>[]cd</a></div>',
+                    });
+                    await testEditor(BasicEditor, {
+                        contentBefore: '<div><a>a[]b</a></div>',
+                        stepFunction: pressEnter,
+                        contentAfter: '<div><a>a<br>[]b</a></div>',
+                    });
+                    await testEditor(BasicEditor, {
+                        contentBefore: '<div><a>ab[]</a></div>',
+                        stepFunction: pressEnter,
+                        contentAfter: '<div><a>ab</a><br>[]<br></div>',
+                    });
+                    await testEditor(BasicEditor, {
+                        contentBefore: '<div><a>ab[]</a>cd</div>',
+                        stepFunction: pressEnter,
+                        contentAfter: '<div><a>ab</a><br>[]cd</div>',
+                    });
+                });
             });
             describe('With attributes', () => {
                 it('should insert an empty paragraph before a paragraph with a span with a class', async () => {
diff --git a/addons/web_editor/static/lib/odoo-editor/test/utils.js b/addons/web_editor/static/lib/odoo-editor/test/utils.js
index 53eb7f6b495..9b3150518b3 100644
--- a/addons/web_editor/static/lib/odoo-editor/test/utils.js
+++ b/addons/web_editor/static/lib/odoo-editor/test/utils.js
@@ -296,9 +296,10 @@ export async function testEditor(Editor = OdooEditor, spec) {
     const selection = parseTextualSelection(testNode);
 
     const editor = new Editor(testNode, { toSanitize: false });
-    editor.keyboardType = 'PHYSICAL_KEYBOARD';
+    editor.keyboardType = 'PHYSICAL';
     if (selection) {
         setTestSelection(selection);
+        editor._recordHistorySelection();
     } else {
         document.getSelection().removeAllRanges();
     }