diff --git a/.ci/release.gitlab-ci.yml b/.ci/release.gitlab-ci.yml
index 5c7c53b2..8bafffe1 100644
--- a/.ci/release.gitlab-ci.yml
+++ b/.ci/release.gitlab-ci.yml
@@ -77,7 +77,7 @@ release-cloudflared-to-github:
     - ci-image-get-image-ref
     - linux-packaging
     - linux-packaging-fips
-    - package-windows
+    - windows-package-sign
   script:
     - ./.ci/scripts/release-target.sh github-release
 
diff --git a/.ci/scripts/windows/builds.ps1 b/.ci/scripts/windows/builds.ps1
index e4a42ea2..3abae290 100644
--- a/.ci/scripts/windows/builds.ps1
+++ b/.ci/scripts/windows/builds.ps1
@@ -4,6 +4,7 @@ $ProgressPreference = "SilentlyContinue"
 
 $env:TARGET_OS = "windows"
 $env:LOCAL_OS = "windows"
+$TIMESTAMP_RFC3161 = "http://timestamp.digicert.com"
 
 New-Item -Path ".\artifacts" -ItemType Directory
 
@@ -13,6 +14,8 @@ $env:LOCAL_ARCH = "amd64"
 $env:CGO_ENABLED = 1
 & make cloudflared
 if ($LASTEXITCODE -ne 0) { throw "Failed to build cloudflared for amd64" }
+# Sign build
+azuresigntool.exe sign -kvu $env:KEY_VAULT_URL -kvi "$env:KEY_VAULT_CLIENT_ID" -kvs "$env:KEY_VAULT_SECRET" -kvc "$env:KEY_VAULT_CERTIFICATE" -kvt "$env:KEY_VAULT_TENANT_ID" -tr "$TIMESTAMP_RFC3161" -d "Cloudflare Tunnel Daemon" .\cloudflared.exe
 copy .\cloudflared.exe .\artifacts\cloudflared-windows-amd64.exe
 
 Write-Output "Building for 386"
@@ -21,4 +24,6 @@ $env:LOCAL_ARCH = "386"
 $env:CGO_ENABLED = 0
 & make cloudflared
 if ($LASTEXITCODE -ne 0) { throw "Failed to build cloudflared for 386" }
+## Sign build
+azuresigntool.exe sign -kvu $env:KEY_VAULT_URL -kvi "$env:KEY_VAULT_CLIENT_ID" -kvs "$env:KEY_VAULT_SECRET" -kvc "$env:KEY_VAULT_CERTIFICATE" -kvt "$env:KEY_VAULT_TENANT_ID" -tr "$TIMESTAMP_RFC3161" -d "Cloudflare Tunnel Daemon" .\cloudflared.exe
 copy .\cloudflared.exe .\artifacts\cloudflared-windows-386.exe
diff --git a/.ci/scripts/windows/sign-msi.ps1 b/.ci/scripts/windows/sign-msi.ps1
new file mode 100644
index 00000000..9f29cd79
--- /dev/null
+++ b/.ci/scripts/windows/sign-msi.ps1
@@ -0,0 +1,26 @@
+# Sign Windows artifacts using azuretool
+# This script processes MSI files from the artifacts directory
+
+$ErrorActionPreference = "Stop"
+
+# Define paths
+$ARTIFACT_DIR = "artifacts"
+$TIMESTAMP_RFC3161 = "http://timestamp.digicert.com"
+
+Write-Host "Looking for Windows artifacts to sign in $ARTIFACT_DIR..."
+
+# Find all Windows MSI files
+$msiFiles = Get-ChildItem -Path $ARTIFACT_DIR -Filter "cloudflared-windows-*.msi" -ErrorAction SilentlyContinue
+
+if ($msiFiles.Count -eq 0) {
+    Write-Host "No Windows MSI files found in $ARTIFACT_DIR"
+    exit 1
+}
+
+Write-Host "Found $($msiFiles.Count) file(s) to sign:"
+foreach ($file in $msiFiles) {
+    Write-Host "Running azuretool sign for $($file.Name)"
+    azuresigntool.exe sign -kvu $env:KEY_VAULT_URL -kvi "$env:KEY_VAULT_CLIENT_ID" -kvs "$env:KEY_VAULT_SECRET" -kvc "$env:KEY_VAULT_CERTIFICATE" -kvt "$env:KEY_VAULT_TENANT_ID" -tr "$TIMESTAMP_RFC3161" -d "Cloudflare Tunnel Daemon" .\\$ARTIFACT_DIR\\$($file.Name)
+}
+
+Write-Host "Signing process completed"
diff --git a/.ci/windows.gitlab-ci.yml b/.ci/windows.gitlab-ci.yml
index 9a35edb6..4a1bb35a 100644
--- a/.ci/windows.gitlab-ci.yml
+++ b/.ci/windows.gitlab-ci.yml
@@ -14,7 +14,7 @@ include:
 ##########################################
 ### Build Cloudflared Windows Binaries ###
 ##########################################
-build-cloudflared-windows:
+windows-build-cloudflared:
   <<: *windows-build-defaults
   stage: build
   script:
@@ -26,7 +26,7 @@ build-cloudflared-windows:
 ######################################################
 ### Load Environment Variables for Component Tests ###
 ######################################################
-load-windows-env-variables:
+windows-load-env-variables:
   stage: pre-build
   extends: .component-tests
   script:
@@ -35,8 +35,29 @@ load-windows-env-variables:
     - echo "DNS_API_TOKEN=$DNS_API_TOKEN" >> windows.env
     # We have to encode the `COMPONENT_TESTS_ORIGINCERT` secret, because it content is a file, otherwise we can't export it using gitlab
     - echo "COMPONENT_TESTS_ORIGINCERT=$(echo "$COMPONENT_TESTS_ORIGINCERT" | base64 -w0)" >> windows.env
+    - echo "KEY_VAULT_URL=$KEY_VAULT_URL" >> windows.env
+    - echo "KEY_VAULT_CLIENT_ID=$KEY_VAULT_CLIENT_ID" >> windows.env
+    - echo "KEY_VAULT_TENANT_ID=$KEY_VAULT_TENANT_ID" >> windows.env
+    - echo "KEY_VAULT_SECRET=$KEY_VAULT_SECRET" >> windows.env
+    - echo "KEY_VAULT_CERTIFICATE=$KEY_VAULT_CERTIFICATE" >> windows.env
   variables:
     COMPONENT_TESTS_CONFIG_CONTENT: Y2xvdWRmbGFyZWRfYmluYXJ5OiAuL2Nsb3VkZmxhcmVkLmV4ZQpjcmVkZW50aWFsc19maWxlOiBjcmVkLmpzb24Kb3JpZ2luY2VydDogY2VydC5wZW0Kem9uZV9kb21haW46IGFyZ290dW5uZWx0ZXN0LmNvbQp6b25lX3RhZzogNDg3OTZmMWU3MGJiNzY2OWMyOWJiNTFiYTI4MmJmNjU=
+  secrets:
+    KEY_VAULT_URL:
+      vault: gitlab/cloudflare/tun/cloudflared/_dev/azure_vault/app_info/key_vault_url@kv
+      file: false
+    KEY_VAULT_CLIENT_ID:
+      vault: gitlab/cloudflare/tun/cloudflared/_dev/azure_vault/app_info/key_vault_client_id@kv
+      file: false
+    KEY_VAULT_TENANT_ID:
+      vault: gitlab/cloudflare/tun/cloudflared/_dev/azure_vault/app_info/key_vault_tenant_id@kv
+      file: false
+    KEY_VAULT_SECRET:
+      vault: gitlab/cloudflare/tun/cloudflared/_dev/azure_vault/secret/key_vault_secret@kv
+      file: false
+    KEY_VAULT_CERTIFICATE:
+      vault: gitlab/cloudflare/tun/cloudflared/_dev/azure_vault/certificate/key_vault_certificate@kv
+      file: false
   artifacts:
     access: 'none'
     reports:
@@ -45,12 +66,12 @@ load-windows-env-variables:
 ###################################
 ### Run Windows Component Tests ###
 ###################################
-component-tests-cloudflared-windows:
+windows-component-tests-cloudflared:
   <<: *windows-build-defaults
   stage: test
-  needs: ["load-windows-env-variables"]
+  needs: ["windows-load-env-variables"]
   script:
-    # We have to decode the secret we encoded on the `load-windows-env-variables` job
+    # We have to decode the secret we encoded on the `windows-load-env-variables` job
     - $env:COMPONENT_TESTS_ORIGINCERT = [System.Text.Encoding]::UTF8.GetString([System.Convert]::FromBase64String($env:COMPONENT_TESTS_ORIGINCERT))
     - powershell -ExecutionPolicy Bypass -File ".\.ci\scripts\windows\go-wrapper.ps1" "${GO_VERSION}" ".\.ci\scripts\windows\component-test.ps1"
   artifacts:
@@ -60,13 +81,13 @@ component-tests-cloudflared-windows:
 ################################
 ### Package Windows Binaries ###
 ################################
-package-windows:
+windows-package:
   rules:
     - !reference [.default-rules, run-on-master]
   stage: package
   needs:
     - ci-image-get-image-ref
-    - build-cloudflared-windows
+    - windows-build-cloudflared
   image: $BUILD_IMAGE
   script:
     - .ci/scripts/package-windows.sh
@@ -74,3 +95,20 @@ package-windows:
   artifacts:
     paths:
       - artifacts/*
+
+#############################
+### Sign Windows Binaries ###
+#############################
+windows-package-sign:
+  <<: *windows-build-defaults
+  rules:
+    - !reference [.default-rules, run-on-master]
+  stage: package
+  needs:
+    - windows-package
+    - windows-load-env-variables
+  script:
+    - powershell -ExecutionPolicy Bypass -File ".\.ci\scripts\windows\sign-msi.ps1"
+  artifacts:
+    paths:
+      - artifacts/*