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 6abe41ccd45..d02e4bc94f9 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
@@ -2172,6 +2172,10 @@ export class OdooEditor extends EventTarget {
             }
         }
         let insertedZws;
+        let { startContainer: start, startOffset, endContainer: end, endOffset } = range;
+        const startBlock = closestBlock(start);
+        const endBlock = closestBlock(end);
+        const [firstLeafOfStartBlock, lastLeafOfEndBlock] = [firstLeaf(startBlock), lastLeaf(endBlock)];
         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
@@ -2184,12 +2188,16 @@ export class OdooEditor extends EventTarget {
             range.startContainer.before(zws);
             insertedZws = zws;
         }
-        let { startContainer: start, startOffset, endContainer: end, endOffset } = range;
-        const [startBlock, endBlock] = [closestBlock(start), closestBlock(end)];
+        // Do not join blocks in the following cases:
+        // 1. start and end share a common ancestor block with the range
+        // 2. selection spans multiple TDs
+        // 3. selection starts at beginning of startBlock and ends at end of
+        //    endBlock
         const doJoin =
-            (startBlock !== closestBlock(range.commonAncestorContainer) ||
-            endBlock !== closestBlock(range.commonAncestorContainer))
-            && (startBlock.tagName !== 'TD' && endBlock.tagName !== 'TD');
+            !(startBlock === closestBlock(range.commonAncestorContainer) &&
+                endBlock === closestBlock(range.commonAncestorContainer))
+            && (startBlock.tagName !== 'TD' && endBlock.tagName !== 'TD')
+            && !(firstLeafOfStartBlock === start && lastLeafOfEndBlock === end);
         let next = nextLeaf(end, this.editable);
 
         // Get the boundaries of the range so as to get the state to restore.
@@ -2210,6 +2218,12 @@ export class OdooEditor extends EventTarget {
         const contents = range.extractContents();
 
         setSelection(start, nodeSize(start));
+        const startLi = closestElement(start, 'li');
+        // Uncheck a list item with empty text in multi-list selection.
+        if (startLi && startLi.classList.contains('o_checked') &&
+            startLi.textContent === '\u200B' && closestElement(end, 'li') !== startLi) {
+            startLi.classList.remove('o_checked');
+        }
         range = getDeepRange(this.editable, { sel });
         // Restore unremovables removed by extractContents.
         [...contents.querySelectorAll('*')].filter(isUnremovable).forEach(n => {
diff --git a/addons/web_editor/static/src/js/editor/odoo-editor/test/spec/list.test.js b/addons/web_editor/static/src/js/editor/odoo-editor/test/spec/list.test.js
index d7b7852160e..8bd7e368438 100644
--- a/addons/web_editor/static/src/js/editor/odoo-editor/test/spec/list.test.js
+++ b/addons/web_editor/static/src/js/editor/odoo-editor/test/spec/list.test.js
@@ -5426,6 +5426,15 @@ describe('List', () => {
                                 '<h1>a[]i</h1><custom-block style="display: block;"><ol><li>jk</li></ol></custom-block>',
                         });
                     });
+                    it('should not join the next list with the first one on delete range', async () => {
+                        await testEditor(BasicEditor, {
+                            contentBefore:
+                                '<ol><li>ab</li><li>[cd</li><li>ef]</li><li>gh</li></ol>',
+                            stepFunction: deleteBackward,
+                            contentAfter:
+                                '<ol><li>ab</li><li>[]<br></li><li>gh</li></ol>',
+                        });
+                    });
                 });
                 describe('Unordered', () => {
                     it('should delete text within a list item', async () => {
@@ -5518,6 +5527,15 @@ describe('List', () => {
                                 '<h1>a[]i</h1><custom-block style="display: block;"><ul><li>jk</li></ul></custom-block>',
                         });
                     });
+                    it('should not join the next list with the first one on delete range', async () => {
+                        await testEditor(BasicEditor, {
+                            contentBefore:
+                                '<ul><li>ab</li><li>[cd</li><li>ef]</li><li>gh</li></ul>',
+                            stepFunction: deleteBackward,
+                            contentAfter:
+                                '<ul><li>ab</li><li>[]<br></li><li>gh</li></ul>',
+                        });
+                    });
                 });
                 describe('Checklist', () => {
                     it('should delete text within a checklist item', async () => {
@@ -5678,6 +5696,36 @@ describe('List', () => {
                                 '<h1>a[]i</h1><custom-block style="display:block;"><ul class="o_checklist"><li class="o_checked">jk</li></ul></custom-block>',
                         });
                     });
+                    it('should not join the next list with the first one on delete range', async () => {
+                        await testEditor(BasicEditor, {
+                            removeCheckIds: true,
+                            contentBefore:
+                                '<ul class="o_checklist"><li>ab</li><li class="o_checked">[cd</li><li>ef]</li><li>gh</li></ul>',
+                            stepFunction: deleteBackward,
+                            contentAfter:
+                                '<ul class="o_checklist"><li>ab</li><li>[]<br></li><li>gh</li></ul>',
+                        });
+                    });
+                    it('should remove the o_checked class on delete range', async () => {
+                        await testEditor(BasicEditor, {
+                            removeCheckIds: true,
+                            contentBefore:
+                                '<ul class="o_checklist"><li>ab</li><li class="o_checked"><a href="#">[cd</a></li><li>ef]</li><li>gh</li></ul>',
+                            stepFunction: deleteBackward,
+                            contentAfter:
+                                '<ul class="o_checklist"><li>ab</li><li>[]<br></li><li>gh</li></ul>',
+                        });
+                    });
+                    it('should remove the o_checked class on delete range (2)', async () => {
+                        await testEditor(BasicEditor, {
+                            removeCheckIds: true,
+                            contentBefore:
+                                '<ul class="o_checklist"><li>ab</li><li class="o_checked"><h1>[cd</h1></li><li>ef]</li><li>gh</li></ul>',
+                            stepFunction: deleteBackward,
+                            contentAfter:
+                                '<ul class="o_checklist"><li>ab</li><li><h1>[]<br></h1></li><li>gh</li></ul>',
+                        });
+                    });
                 });
                 describe('Mixed', () => {
                     describe('Ordered to unordered', () => {