Idea: After completing interviews with free trial participants and while conducting a design audit, I realized we weren’t visually distinguishing free premium suggestions from regular ones. If users quickly accept or dismiss a suggestion, they might not notice it was premium. Given that our premium branding is gold, I proposed introducing a distinct yellow underline specifically for premium suggestions to make them stand out more effectively.

Hypothesis: Showing users yellow underlines after they have accepted or dismissed all free inline suggestions, coupled with the "advanced issues" upgrade hook will increase subscription upgrades because it will introduce a new audience (free users who do not open the assistant) to the impact of Premium.

Good Friction: Initially, we had the yellow underlines mimic the free suggestions interaction. When users hovered over a yellow underline, an inline card would appear, informing them of available premium suggestions and prompting them to subscribe. However, we identified a significant issue: users who hovered over multiple yellow underlines were repeatedly shown the same message, creating a redundant and frustrating experience.

To resolve this, we shifted to a click interaction instead of hover and implemented show and cool-down logic. This refined approach not only enhanced the user experience by reducing frustration but also maintained a clear visual cue to demonstrate the value of Premium effectively.