Is free trial conversion a copy problem or a timing problem?

Our 14 day free trial has a solid signup rate but most users go quiet around day 8 without reaching key milestones. We tried tweaking our onboarding emails and in-app nudges, but the drop-off barely moved.

It made me realize that forcing users into a fixed timeframe might be asking for commitment before they’ve experienced real value.

How did you optimize your trial conversion did you shorten the trial, switch to freemium, or change when you ask for payment?