diff --git a/Casks/t/tastytrade.rb b/Casks/t/tastytrade.rb
index 4cd9ab9e2c..eaa887d966 100644
--- a/Casks/t/tastytrade.rb
+++ b/Casks/t/tastytrade.rb
@@ -1,17 +1,38 @@
 cask "tastytrade" do
   arch arm: "-aarch64"
 
-  version "2.5.4"
-  sha256 arm:   "51f21ecd02cd7b0acf13d80f712e87a2a163d79a8b1721cebc78559deb1615fe",
-         intel: "da585b646afba35104957cbfb433c4b27cc9f1ee6fd69f3a045397c3a27d5c7f"
+  version "2.8.0"
+  sha256 arm:   "62532bc7b23a439e501c0eff1c3bab216adcbc5c64c05539d06fcdf5d1705088",
+         intel: "98ace9292f65022780328fb3a61c98c6542e62046390770d16b8942a9b9e6be8"
 
   url "https://download.tastytrade.com/desktop-#{version.major}.x.x/#{version}/tastytrade-#{version}#{arch}.dmg"
   name "tastytrade"
   desc "Desktop trading platform"
   homepage "https://tastytrade.com/technology/"
 
+  # The version information is found in a random JSON file, which is referenced
+  # from another JSON file. We can't tell which file will contain the version
+  # information, so we check each until we find a match. As of writing, the
+  # first JSON file contains the version information but this check could
+  # involve further requests if the order of the JSON files changes or the
+  # structure of the target JSON file changes. The latter would cause the check
+  # to fetch all the JSON files before failing, which isn't ideal.
   livecheck do
-    skip "No version information available"
+    url "https://tastytrade.com/page-data/technology/page-data.json"
+    strategy :json do |json|
+      requests = 0
+      version = json["staticQueryHashes"]&.each do |static_hash|
+        requests += 1
+        break if requests > 4
+
+        content = Homebrew::Livecheck::Strategy.page_content("https://tastytrade.com/page-data/sq/d/#{static_hash}.json")
+        next if content.blank? || content[:content].blank?
+
+        hash_json = JSON.parse(content[:content])
+        version = hash_json.dig("data", "contentstackGlobalSettings", "tastyworksSoftware", "desktopVersion")
+        break version if version.present?
+      end
+    end
   end
 
   auto_updates true