1. in a way that shows deep insight or understanding
2. in a way that pierces through or goes deeply into something
3. in an intensely direct or searching manner

Examples

• She looked at him penetratingly, as if trying to read his thoughts.
• The critic analyzed the novel penetratingly, revealing hidden themes.
• The cold wind blew penetratingly through the thin jacket.
• His penetratingly honest questions made everyone uncomfortable.
• The detective stared penetratingly at the suspect during questioning.
• The sound penetratingly cut through the silence of the night.
• She spoke penetratingly about the social issues affecting the community.