Applying formatting across multiple list items breaks list structure

Phenomenon

When selecting text across multiple list items and applying formatting in Chrome, the list structure may break. List items may be converted to paragraphs or the list may be removed entirely.

Reproduction example

1. Create a list: <ul><li>Item 1</li><li>Item 2</li><li>Item 3</li></ul>
2. Select text across “Item 1” and “Item 2”
3. Apply bold formatting

Observed behavior

• List items may be converted to paragraphs
• List structure is broken
• Formatting is applied but list is lost
• DOM structure becomes: <p><b>Item 1</b></p><p><b>Item 2</b></p>

Expected behavior

• List structure should be maintained
• Formatting should be applied within list items
• List items should remain as <li> elements
• Structure should not break

Browser Comparison

• Chrome/Edge: May break structure (this case)
• Firefox: More likely to break structure
• Safari: Most likely to break structure

Notes and possible direction for workarounds

• Intercept formatting across list items
• Apply formatting within each list item separately
• Preserve list structure
• Normalize structure after formatting