Repology.org, besides offering a convenient package search for distros offering packages, and including Cygwin in those, repology.org also tracks whether the packages are up to date, optionally by maintainer, and offers an Atom/RSS feed of that status.
For example, see: https://repology.org/maintainer/yaakov.selkowitz@cygwin/feed-for-repo/cygwin and plug your own (or anyone else's) names in there and subscribe to your own package status feed. I find it provides me with motivation as well as notification to keep my packages updated, and is useful when your own package update checker doesn't run or you break it! Just don't get obsessed with keeping everything updated daily, even if you have a lot of free time to fill! -- Take care. Thanks, Brian Inglis, Calgary, Alberta, Canada This email may be disturbing to some readers as it contains too much technical detail. Reader discretion is advised. [Data in binary units and prefixes, physical quantities in SI.]