diff --git a/Formula/f/flexget.rb b/Formula/f/flexget.rb
index e4c18332607f..98022951ac96 100644
--- a/Formula/f/flexget.rb
+++ b/Formula/f/flexget.rb
@@ -3,17 +3,17 @@ class Flexget < Formula
 
   desc "Multipurpose automation tool for content"
   homepage "https://www.flexget.com"
-  url "https://files.pythonhosted.org/packages/41/cc/dbcba4d30ede129282581a8f46d9b5f7acc0c47bd5e68d53fc424f3fee3c/flexget-3.18.43.tar.gz"
-  sha256 "698f8c5f2e1fa29908cda94c4856dcc18cf2d2376a717bf8b78c40c2013df18f"
+  url "https://files.pythonhosted.org/packages/4e/8e/6a8e33e402825e13c2c5824ec1c0077ff39f7016552728ef04395950ae76/flexget-3.18.44.tar.gz"
+  sha256 "1d6e595b1644f6c7aca164b11f0006fb9be1898f9b98cf8fd629d3aea848fce0"
   license "MIT"
 
   bottle do
-    sha256 cellar: :any,                 arm64_tahoe:   "e3a31456a62f0924c0570312bed1a2dc996540c61119f3716ed8c573dc456535"
-    sha256 cellar: :any,                 arm64_sequoia: "611d86146cbd0061d4e16a1689d08e52fa299578f899e819d6200d5a1dd05479"
-    sha256 cellar: :any,                 arm64_sonoma:  "6eab257b28fcae9b0b4e7548df133a949cf3062de2f58aa98c25759f8f279277"
-    sha256 cellar: :any,                 sonoma:        "d8e6f029d9bd7d1a46f3f36725d442078162d9002b75e671d151cd83b217da1c"
-    sha256 cellar: :any_skip_relocation, arm64_linux:   "4dbf80d5403f1ccdb1bf87ca43828a80cb60df99cbba022e277061209bfd7433"
-    sha256 cellar: :any_skip_relocation, x86_64_linux:  "cd4293c53d3f55a187fa2ba61653be8f48d561c91d445d9d637d78f676781c47"
+    sha256 cellar: :any,                 arm64_tahoe:   "b306aed220619b130f043c190b11d87f92f6656bd3e00f2491f5700a37c50a71"
+    sha256 cellar: :any,                 arm64_sequoia: "799ab5e5840185f4373158cfbfab606a04e8928bbc6a02712919884e5b7172c1"
+    sha256 cellar: :any,                 arm64_sonoma:  "310465a4adb33dc9a37ab6c686a19af35b89e29c137f0a93ea7d1cb3106e2e69"
+    sha256 cellar: :any,                 sonoma:        "b6283f671847041bfbd303ebd4b38839500a64c6357c2bff615dd71134394bf5"
+    sha256 cellar: :any_skip_relocation, arm64_linux:   "a4f48dfb45543dd076f44ee94ba0bdd3ffe2f27f11f10555438e1f73e33c3393"
+    sha256 cellar: :any_skip_relocation, x86_64_linux:  "e20694e448586395772679e37cc795fc755be124abec3328c1040cc0679f6c01"
   end
 
   depends_on "rust" => :build
@@ -135,6 +135,13 @@ class Flexget < Formula
       url "https://github.com/html5lib/html5lib-python/commit/b90dafff1bf342d34d539098013d0b9f318c7641.patch?full_index=1"
       sha256 "779f8bab52308792b7ac2f01c3cd61335587640f98812c88cb074dce9fe8162d"
     end
+
+    # Python 3.14 with setuptools 81+ compatibility (`pkg_resources` removal)
+    # upstream pr ref, https://github.com/html5lib/html5lib-python/pull/592
+    patch do
+      url "https://github.com/html5lib/html5lib-python/commit/1dbc19cd6db72cb919885827bc4883423e0cb647.patch?full_index=1"
+      sha256 "5951b823f353dd70806ad6e163ab8f46899496c1e8bb53970c99abe8d1df1a78"
+    end
   end
 
   resource "idna" do
@@ -168,8 +175,8 @@ class Flexget < Formula
   end
 
   resource "jaraco-text" do
-    url "https://files.pythonhosted.org/packages/4f/00/1b4dbbc5c6dcb87a4278cc229b2b560484bf231bba7922686c5139e5f934/jaraco_text-4.0.0.tar.gz"
-    sha256 "5b71fecea69ab6f939d4c906c04fee1eda76500d1641117df6ec45b865f10db0"
+    url "https://files.pythonhosted.org/packages/f2/20/f071dfb40f06fd0395167a40218c10adb7164635f65ebdafe45e0c714935/jaraco_text-4.2.0.tar.gz"
+    sha256 "194e386aa5b15a6616019df87a6b29c00fd3c9c8b0475731b64633ca7afd495b"
   end
 
   resource "jinja2" do
@@ -293,8 +300,8 @@ class Flexget < Formula
   end
 
   resource "setuptools" do
-    url "https://files.pythonhosted.org/packages/76/95/faf61eb8363f26aa7e1d762267a8d602a1b26d4f3a1e758e92cb3cb8b054/setuptools-80.10.2.tar.gz"
-    sha256 "8b0e9d10c784bf7d262c4e5ec5d4ec94127ce206e8738f29a437945fbc219b70"
+    url "https://files.pythonhosted.org/packages/82/f3/748f4d6f65d1756b9ae577f329c951cda23fb900e4de9f70900ced962085/setuptools-82.0.0.tar.gz"
+    sha256 "22e0a2d69474c6ae4feb01951cb69d515ed23728cf96d05513d36e42b62b37cb"
   end
 
   resource "sgmllib3k" do