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The warning signs
Book balances that never match statements, an ever-growing 'Ask my accountant' account, duplicate vendor records, negative inventory, payroll liabilities that never clear, prior-year balances that changed after filing, and reports that you no longer trust enough to use.
One of these on its own is a fixable slip. Three or more together usually means the underlying structure needs work, not just the current month.
What a cleanup actually involves
A cleanup rebuilds periods from source data, corrects categorisation, removes duplicates and reconciles every account. It ends with a written summary of what changed, so your tax preparer is not left guessing.
Preventing a repeat
Cleanups recur when the process that caused them stays unchanged. A documented chart of accounts, a fixed monthly close calendar and a reviewer other than the preparer usually prevent the second cleanup.