1. in a way that presents a difficult problem or test; in a manner that requires effort or skill to overcome
2. in a way that questions, disputes, or provokes someone; in a manner that expresses doubt or defiance

Examples

• The new software was challengingly complex for beginners to learn.
• She looked at him challengingly, as if daring him to disagree.
• The coach spoke challengingly to the team about their recent poor performance.
• The exam questions were challengingly worded and required careful reading.
• He raised his eyebrows challengingly when she made that claim.
• The project proved challengingly difficult to complete on schedule.