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 2c699d2423f..d452fff29be 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
@@ -1853,6 +1853,19 @@ export class OdooEditor extends EventTarget {
                 range.setEnd(commonAncestorContainer, nodeSize(commonAncestorContainer));
             }
         }
+        let insertedZws;
+        if (sel && !sel.isCollapsed && !range.startOffset && !range.startContainer.previousSibling) {
+            // Insert a zero-width space before the selection if the selection
+            // is non-collapsed and at the beginning of its parent, so said
+            // parent will have content after extraction. This ensures that the
+            // parent will not be removed by "tricking" `range.extractContents`.
+            // Eg, <h1><font>[...]</font></h1> will preserve the styles of the
+            // <font> node. If it remains empty, it will be cleaned up later by
+            // the sanitizer.
+            const zws = document.createTextNode('\u200B');
+            range.startContainer.before(zws);
+            insertedZws = zws;
+        }
         let start = range.startContainer;
         let end = range.endContainer;
         // Let the DOM split and delete the range.
@@ -1925,6 +1938,14 @@ export class OdooEditor extends EventTarget {
                 break;
             }
         }
+        if (insertedZws) {
+            // Remove the zero-width space (zws) that was added to preserve the
+            // parent styles, then call `fillEmpty` to properly add a flagged
+            // zws if still needed.
+            const el = closestElement(insertedZws);
+            insertedZws.remove();
+            el && fillEmpty(el);
+        }
         next = range.endContainer && rightLeafOnlyNotBlockPath(range.endContainer).next().value;
         if (
             shouldPreserveSpace && next && !(next && next.nodeType === Node.TEXT_NODE && next.textContent.startsWith(' '))
diff --git a/addons/web_editor/static/src/js/editor/odoo-editor/test/spec/editor.test.js b/addons/web_editor/static/src/js/editor/odoo-editor/test/spec/editor.test.js
index e17d8074a7e..8041867dfa7 100644
--- a/addons/web_editor/static/src/js/editor/odoo-editor/test/spec/editor.test.js
+++ b/addons/web_editor/static/src/js/editor/odoo-editor/test/spec/editor.test.js
@@ -1003,11 +1003,16 @@ X[]
                     contentAfter: '<div>a<p>b[]e</p>f</div>',
                 });
             });
-            it('should delete empty nodes ', async () => {
+            it('should not delete single remaining empty inline', async () => {
                 // Forward selection
                 await testEditor(BasicEditor, {
                     contentBefore: '<h1><font>[abcdef]</font></h1>',
                     stepFunction: deleteForward,
+                    // The flagged 200B is there to preserve the font so if we
+                    // write now, we still write in the font element's style.
+                    contentAfterEdit: '<h1><font data-oe-zws-empty-inline="">[]\u200B</font><br></h1>',
+                    // The flagged 200B is removed by the sanitizer if its
+                    // parent remains empty.
                     contentAfter: '<h1>[]<br></h1>',
                 });
             });
diff --git a/addons/web_editor/static/src/js/editor/odoo-editor/test/spec/insert.test.js b/addons/web_editor/static/src/js/editor/odoo-editor/test/spec/insert.test.js
index f0d0cb7a4a5..d5e2e9552e3 100644
--- a/addons/web_editor/static/src/js/editor/odoo-editor/test/spec/insert.test.js
+++ b/addons/web_editor/static/src/js/editor/odoo-editor/test/spec/insert.test.js
@@ -1,5 +1,5 @@
 import { parseHTML } from '../../src/utils/utils.js';
-import { BasicEditor, testEditor, unformat } from '../utils.js';
+import { BasicEditor, testEditor, unformat, insertText, deleteBackward } from '../utils.js';
 
 const span = text => {
     const span = document.createElement('span');
@@ -264,3 +264,22 @@ describe('insert HTML', () => {
         });
     });
 });
+describe('insert text', () => {
+    describe('not collapsed selection', () => {
+        it('should insert a character in a fully selected font in a heading, preserving its style', async () => {
+            await testEditor(BasicEditor, {
+                contentBefore: '<h1><font style="background-color: red;">[abc</font><br></h1><p>]def</p>',
+                stepFunction: async editor => insertText(editor, 'g'),
+                contentAfter: '<h1><font style="background-color: red;">g[]</font><br></h1><p>def</p>',
+            });
+            await testEditor(BasicEditor, {
+                contentBefore: '<h1><font style="background-color: red;">[abc</font><br></h1><p>]def</p>',
+                stepFunction: async editor => {
+                    await deleteBackward(editor);
+                    await insertText(editor, 'g');
+                },
+                contentAfter: '<h1><font style="background-color: red;">g[]</font><br></h1><p>def</p>',
+            });
+        });
+    });
+});