What happens to searchable messages on the Free plan when I reach the limit?
Space will archive your oldest messages and store them. These messages will be preserved, and they will become available to you as soon as you upgrade your organization to a paid plan.
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Will they reset after a certain period (like a month) or will they be accumulated from the beginning?
Acecards13 They accumulate from the beginning. When you reach the limit, older messages will be hidden and new messages will be still visible.