diff --git a/Casks/i/inso.rb b/Casks/i/inso.rb
index 9570c73029..977fafa204 100644
--- a/Casks/i/inso.rb
+++ b/Casks/i/inso.rb
@@ -1,6 +1,6 @@
 cask "inso" do
-  version "2023.5.8"
-  sha256 "2ab577f3b3e0e0afc7080b24908c248a31863a7ae1d6d81595e5d16d0238ec58"
+  version "8.1.0"
+  sha256 "b1fc1c0e4156e20d92d433ce545be0886d07f8e735a789319e1cb3962af94db5"
 
   url "https://github.com/Kong/insomnia/releases/download/lib%40#{version}/inso-macos-#{version}.zip",
       verified: "github.com/Kong/insomnia/"
@@ -8,8 +8,12 @@ cask "inso" do
   desc "CLI HTTP and GraphQL Client"
   homepage "https://insomnia.rest/products/inso"
 
+  # Upstream previously used a date-based version scheme (e.g., `2023.5.8`)
+  # before switching to a typical `8.1.0` format. The date-based versions are
+  # numerically higher, so we have to avoid matching them.
   livecheck do
-    regex(/lib@v?(\d+(?:\.\d+)+)(?!.)/i)
+    url :url
+    regex(/^lib@v?(\d{1,3}(?:\.\d+)+)$/i)
   end
 
   conflicts_with cask: "homebrew/cask-versions/inso-beta"
diff --git a/Casks/i/insomnia.rb b/Casks/i/insomnia.rb
index 15aa8e82a1..c5dd1e9b69 100644
--- a/Casks/i/insomnia.rb
+++ b/Casks/i/insomnia.rb
@@ -1,6 +1,6 @@
 cask "insomnia" do
-  version "2023.5.8"
-  sha256 "40c640dcb17bc9d3a66e2afc82c28fac4c78f92aaccf72c4aea14fdfd984847f"
+  version "8.1.0"
+  sha256 "f011d0bead17b5784a915873d9ba4513fcb4a1ed07cfc9e43af459b5dcc10b39"
 
   url "https://github.com/Kong/insomnia/releases/download/core%40#{version}/Insomnia.Core-#{version}.dmg",
       verified: "github.com/Kong/insomnia/"
@@ -8,8 +8,12 @@ cask "insomnia" do
   desc "HTTP and GraphQL Client"
   homepage "https://insomnia.rest/"
 
+  # Upstream previously used a date-based version scheme (e.g., `2023.5.8`)
+  # before switching to a typical `8.1.0` format. The date-based versions are
+  # numerically higher, so we have to avoid matching them.
   livecheck do
-    regex(/core@v?(\d+(?:\.\d+)+)(?!.)/i)
+    url :url
+    regex(/^core@v?(\d{1,3}(?:\.\d+)+)$/i)
   end
 
   auto_updates true