diff --git a/Casks/t/tunnelbear.rb b/Casks/t/tunnelbear.rb
index 50a8726fc2..5b703f6769 100644
--- a/Casks/t/tunnelbear.rb
+++ b/Casks/t/tunnelbear.rb
@@ -2,25 +2,36 @@ cask "tunnelbear" do
   on_catalina :or_older do
     version "4.1.8"
     sha256 "60c332511b91b794405249132ceb0c88e999b070c087b5f70f1cf09a84e5e5e9"
+
+    url "https://s3.amazonaws.com/tunnelbear/downloads/mac/TunnelBear-#{version}.zip",
+        verified: "s3.amazonaws.com/tunnelbear/downloads/mac/"
+
+    depends_on macos: ">= :sierra"
   end
   on_big_sur :or_newer do
-    version "5.1.0"
-    sha256 "80b7ddebacb08de0c29e4beffae70ba1c536056f6ec6d668e7845ddd8b3105e2"
+    version "5.1.1"
+    sha256 :no_check
+
+    url "https://s3.amazonaws.com/tunnelbear/downloads/mac/TunnelBear.zip",
+        verified: "s3.amazonaws.com/tunnelbear/downloads/mac/"
+
+    depends_on macos: ">= :big_sur"
   end
 
-  url "https://s3.amazonaws.com/tunnelbear/downloads/mac/TunnelBear-#{version}.zip",
-      verified: "s3.amazonaws.com/tunnelbear/downloads/mac/"
   name "TunnelBear"
   desc "VPN client for secure internet access and private browsing"
   homepage "https://www.tunnelbear.com/"
 
+  # Older versions may have a more recent `pubDate` than newer versions, so we
+  # have to check all the items in the appcast.
   livecheck do
     url "https://tunnelbear.s3.amazonaws.com/downloads/mac/appcast.xml"
-    strategy :sparkle, &:short_version
+    strategy :sparkle do |items|
+      items.map(&:short_version)
+    end
   end
 
   auto_updates true
-  depends_on macos: ">= :sierra"
 
   app "TunnelBear.app"