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How long does a calendar change take to reach Jira?

For a calendar you connected yourself, about 5 minutes, or at once with Reload.

Neither calendar integration reacts as the change happens. The app reads a personal Outlook or Google connection again once its stored copy is more than 5 minutes old, and Reload on My Rules reads it at once. A Microsoft 365 connection that an administrator set up for the whole site is read at most every 15 minutes. Cancelling an entry or switching automatic replies off removes the rules on the same cycle. Searches with the app's JQL fields use a stored status that is refreshed about once an hour, and again when someone opens the Out of Office panel on a work item.