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Keep parked logins alive says what daily renewal does and how to turn it on.

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A parked login has expired

pitboard status shows login expired beside the account, and Pitboard’s menu shows Needs signing in again. Sign in to the account again, then turn on daily renewal to keep it from happening.

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Daily renewal stopped working

pitboard doctor flags its renewal schedule line: Turn daily renewal off and on again: with Renew parked logins daily in the app’s Renewal settings, or on the command line:
Where the last run failed, run pitboard renew to see what it says. Renewal schedule lists where each system keeps the schedule.

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The schedule uses another proxy

pitboard doctor warns on its renewal schedule's proxy line when the schedule’s proxy differs from your shell’s. Run pitboard schedule install from a shell where the proxy variables are right. The app starts with the system’s environment, not a terminal’s. Turning Renew parked logins daily off and on gives the schedule the app’s proxy variables:

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Pitboard does not start when you sign in

Turn on Open Pitboard at login in Settings > General. If macOS is waiting for you to allow it, click Open Login Items Settings and allow Pitboard there.