diff --git a/Casks/l/lightkey.rb b/Casks/l/lightkey.rb
index a0e80b0e9c..39ca0ec232 100644
--- a/Casks/l/lightkey.rb
+++ b/Casks/l/lightkey.rb
@@ -3,8 +3,21 @@ cask "lightkey" do
     version "4.4.5"
     sha256 "457df4bb2d2f21a52eec9b9b05830eb082014ce66fd79f91544a0838d54a3241"
 
+    # This check should only return legacy versions and the conditions may need
+    # to be updated as the minimum system version of releases changes. If/when
+    # upstream stops publishing new legacy versions, this should be updated to
+    # use `skip` instead.
     livecheck do
-      skip "Legacy version"
+      url "https://lightkeyapp.com/en/update"
+      strategy :sparkle do |items|
+        items.map do |item|
+          next unless item.minimum_system_version
+          next if item.minimum_system_version < :big_sur ||
+                  item.minimum_system_version >= :ventura
+
+          item.version
+        end
+      end
     end
 
     depends_on macos: ">= :big_sur"
@@ -13,8 +26,10 @@ cask "lightkey" do
     version "4.6"
     sha256 "fccd39bd1cde1ff01a04194643bd8d17fc593e4c6b82a058e22e41471fed41a9"
 
-    # Updates for legacy versions are included so sorting by release date
-    # return false positives, pass all version numbers to livecheck instead
+    # Upstream also publishes legacy versions (with a lower minor version) in
+    # the appcast, so the first `item` after sorting by `pubDate`/`version` may
+    # not be the highest version. This `strategy` block collects the `version`
+    # from all `items`, ignoring the `Sparkle` strategy's `pubDate` sorting.
     livecheck do
       url "https://lightkeyapp.com/en/update"
       strategy :sparkle do |items|