Keepwatch

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Most auto-renewal surprises aren't about the expiration date. They come from a notice deadline 30, 60 or 90 days earlier that nobody wrote down. Keepwatch tracks that date for every contract you've signed: vendor agreements, equipment leases, service contracts, software subscriptions and commercial leases. Scan a paper contract on iPhone or drag a PDF onto the Mac. Keepwatch reads it on your device and suggests the dates, notice period and parties for you to confirm. It counts calendar or business days the way the contract does, skipping weekends and U.S. federal holidays, and reminds you ahead of each deadline. When you decide not to renew, it drafts an editable notice letter. There's no Keepwatch server: contracts stay on your devices and in your own iCloud. Free for three contracts; Keepwatch Pro is $4.99 a month or $39.99 a year. Built by a former corporate attorney with 20+ years of contract experience. For iPhone, iPad and Mac.