[Fleet Automation] Add a flag to force install package

.gitlab/deploy_packages/e2e.yml

@@ -1,6 +1,8 @@
-# Jobs that deploy agent packages on QA environment, to be used by e2e tests
+# Jobs that deploy agent packages on QA environment, to be used by e2e tests.
+# We use two separate jobs for Windows and Linux so that a failure in deploying the
+# Linux / Windows script doesn't impact the other OS (i.e. Windows scripts failing to be signed blocking Linux E2E tests).
 
-qa_installer_script:
+qa_installer_script_linux:
   image: registry.ddbuild.io/ci/datadog-agent-buildimages/gitlab_agent_deploy$DATADOG_AGENT_BUILDIMAGES_SUFFIX:$DATADOG_AGENT_BUILDIMAGES
   stage: deploy_packages
   tags: ["arch:amd64"]
@@ -14,3 +16,17 @@ qa_installer_script:
   script:
     - $S3_CP_CMD --recursive --exclude "*" --include "install*.sh" "$OMNIBUS_PACKAGE_DIR" "s3://${INSTALLER_TESTING_S3_BUCKET}/${CI_COMMIT_SHA}/scripts/"
     - $S3_CP_CMD --recursive --exclude "*" --include "install*.sh" "$OMNIBUS_PACKAGE_DIR" "s3://${INSTALLER_TESTING_S3_BUCKET}/pipeline-${CI_PIPELINE_ID}/scripts/"
+
+qa_installer_script_windows:
+  image: registry.ddbuild.io/ci/datadog-agent-buildimages/gitlab_agent_deploy$DATADOG_AGENT_BUILDIMAGES_SUFFIX:$DATADOG_AGENT_BUILDIMAGES
+  stage: deploy_packages
+  tags: ["arch:amd64"]
+  rules:
+    - !reference [.on_installer_or_e2e_changes]
+    - !reference [.manual]
+  needs:
+    - powershell_script_signing
+  before_script:
+    - ls $WINDOWS_POWERSHELL_DIR
+  script:
+    - $S3_CP_CMD $WINDOWS_POWERSHELL_DIR/Install-Datadog.ps1 s3://${INSTALLER_TESTING_S3_BUCKET}/pipeline-${CI_PIPELINE_ID}/scripts/Install-Datadog.ps1

.gitlab/deploy_packages/windows.yml

@@ -51,23 +51,6 @@ deploy_staging_windows_tags-7:
       full=id=3a6e02b08553fd157ae3fb918945dd1eaae5a1aa818940381ef07a430cf25732
 
 # Datadog Installer
-powershell_script_signing:
-  extends: .windows_docker_default
-  stage: deploy_packages
-  needs: []
-  variables:
-    ARCH: "x64"
-  rules:
-    !reference [.on_deploy_installer]
-  artifacts:
-    expire_in: 2 weeks
-    paths:
-      - $WINDOWS_POWERSHELL_DIR
-  script:
-    - mkdir $WINDOWS_POWERSHELL_DIR
-    - docker run --rm -v "$(Get-Location):c:\mnt" -e AWS_NETWORKING=true -e IS_AWS_CONTAINER=true ${WINBUILDIMAGE} powershell -C "dd-wcs sign \mnt\tools\windows\DatadogAgentInstallScript\Install-Datadog.ps1"
-    - copy .\tools\windows\DatadogAgentInstallScript\Install-Datadog.ps1 $WINDOWS_POWERSHELL_DIR\Install-Datadog.ps1
-
 deploy_installer_packages_windows-x64:
   rules:
     !reference [.on_deploy_installer]
@@ -77,6 +60,7 @@ deploy_installer_packages_windows-x64:
   needs: ["windows-installer-amd64", "powershell_script_signing"]
   before_script:
     - ls $OMNIBUS_PACKAGE_DIR
+    - ls $WINDOWS_POWERSHELL_DIR
   script:
     - $S3_CP_CMD
       --recursive

.gitlab/e2e/e2e.yml

@@ -460,7 +460,7 @@ new-e2e-installer-script:
     - deploy_suse_rpm_testing_arm64-a7
     - deploy_suse_rpm_testing_x64-a7
     - deploy_installer_oci
-    - qa_installer_script
+    - qa_installer_script_linux
   variables:
     TARGETS: ./tests/installer/script
     TEAM: fleet
@@ -497,6 +497,7 @@ new-e2e-installer-windows:
     - deploy_windows_testing-a7
     - deploy_installer_oci
     - deploy_agent_oci
+    - qa_installer_script_windows
   before_script:
     # CURRENT_AGENT_VERSION is used to verify the installed agent version
     # Must run before new_e2e_template changes the aws profile
@@ -517,6 +518,7 @@ new-e2e-installer-windows:
       - EXTRA_PARAMS: --run "TestAgentInstalls$"
       - EXTRA_PARAMS: --run "TestAgentUpgrades$"
       # install-script
+      - EXTRA_PARAMS: --run "TestInstallScript$"
       - EXTRA_PARAMS: --run "TestInstallScriptWithAgentUser$"
       # installer-package
       - EXTRA_PARAMS: --run "TestInstaller$"

.gitlab/e2e_install_packages/installer.yml

@@ -13,3 +13,4 @@ qa_installer_script_main:
     - ls $OMNIBUS_PACKAGE_DIR
   script:
     - $S3_CP_CMD --recursive --exclude "*" --include "install*.sh" "$OMNIBUS_PACKAGE_DIR" "s3://${INSTALLER_TESTING_S3_BUCKET}/scripts/"
+

.gitlab/package_build/installer.yml

@@ -115,6 +115,27 @@ installer-install-scripts:
     paths:
       - $OMNIBUS_PACKAGE_DIR
 
+#
+# Windows install script
+#
+powershell_script_signing:
+  extends: .windows_docker_default
+  stage: package_build
+  needs: []
+  variables:
+    ARCH: "x64"
+  rules:
+    - !reference [.except_mergequeue]
+    - when: on_success
+  artifacts:
+    expire_in: 2 weeks
+    paths:
+      - $WINDOWS_POWERSHELL_DIR
+  script:
+    - mkdir $WINDOWS_POWERSHELL_DIR
+    - docker run --rm -v "$(Get-Location):c:\mnt" -e AWS_NETWORKING=true -e IS_AWS_CONTAINER=true ${WINBUILDIMAGE} powershell -C "dd-wcs sign \mnt\tools\windows\DatadogAgentInstallScript\Install-Datadog.ps1"
+    - copy .\tools\windows\DatadogAgentInstallScript\Install-Datadog.ps1 $WINDOWS_POWERSHELL_DIR\Install-Datadog.ps1
+
 #
 # The installer program
 #

cmd/installer/subcommands/installer/command.go

@@ -284,6 +284,7 @@ func setupCommand() *cobra.Command {
 
 func installCommand() *cobra.Command {
 	var installArgs []string
+	var forceInstall bool
 	cmd := &cobra.Command{
 		Use:     "install <url>",
 		Short:   "Install a package",
@@ -296,10 +297,14 @@ func installCommand() *cobra.Command {
 			}
 			defer func() { i.stop(err) }()
 			i.span.SetTag("params.url", args[0])
+			if forceInstall {
+				return i.ForceInstall(i.ctx, args[0], installArgs)
+			}
 			return i.Install(i.ctx, args[0], installArgs)
 		},
 	}
 	cmd.Flags().StringArrayVarP(&installArgs, "install_args", "A", nil, "Arguments to pass to the package")
+	cmd.Flags().BoolVar(&forceInstall, "force", false, "Install packages, even if they are already up-to-date.")
 	return cmd
 }
 

pkg/fleet/daemon/daemon_test.go

@@ -3,9 +3,6 @@
 // This product includes software developed at Datadog (https://www.datadoghq.com/).
 // Copyright 2016-present Datadog, Inc.
 
-// for now the installer is not supported on windows
-//go:build !windows
-
 package daemon
 
 import (
@@ -67,6 +64,11 @@ func (m *testPackageManager) Install(ctx context.Context, url string, installArg
 	return args.Error(0)
 }
 
+func (m *testPackageManager) ForceInstall(ctx context.Context, url string, installArgs []string) error {
+	args := m.Called(ctx, url, installArgs)
+	return args.Error(0)
+}
+
 func (m *testPackageManager) Remove(ctx context.Context, pkg string) error {
 	args := m.Called(ctx, pkg)
 	return args.Error(0)

pkg/fleet/installer/installer.go

@@ -50,6 +50,7 @@ type Installer interface {
 	ConfigStates() (map[string]repository.State, error)
 
 	Install(ctx context.Context, url string, args []string) error
+	ForceInstall(ctx context.Context, url string, args []string) error
 	Remove(ctx context.Context, pkg string) error
 	Purge(ctx context.Context)
 
@@ -151,8 +152,28 @@ func (i *installerImpl) IsInstalled(_ context.Context, pkg string) (bool, error)
 	return hasPackage, nil
 }
 
+// ForceInstall installs or updates a package, even if it's already installed
+func (i *installerImpl) ForceInstall(ctx context.Context, url string, args []string) error {
+	return i.doInstall(ctx, url, args, func(dbPkg db.Package, pkg *oci.DownloadedPackage) bool {
+		if dbPkg.Name == pkg.Name && dbPkg.Version == pkg.Version {
+			log.Warnf("package %s version %s is already installed, updating it anyway", pkg.Name, pkg.Version)
+		}
+		return true
+	})
+}
+
 // Install installs or updates a package.
 func (i *installerImpl) Install(ctx context.Context, url string, args []string) error {
+	return i.doInstall(ctx, url, args, func(dbPkg db.Package, pkg *oci.DownloadedPackage) bool {
+		if dbPkg.Name == pkg.Name && dbPkg.Version == pkg.Version {
+			log.Warnf("package %s version %s is already installed", pkg.Name, pkg.Version)
+			return false
+		}
+		return true
+	})
+}
+
+func (i *installerImpl) doInstall(ctx context.Context, url string, args []string, shouldInstallPredicate func(dbPkg db.Package, pkg *oci.DownloadedPackage) bool) error {
 	i.m.Lock()
 	defer i.m.Unlock()
 	pkg, err := i.downloader.Download(ctx, url) // Downloads pkg metadata only
@@ -168,8 +189,7 @@ func (i *installerImpl) Install(ctx context.Context, url string, args []string)
 	if err != nil && !errors.Is(err, db.ErrPackageNotFound) {
 		return fmt.Errorf("could not get package: %w", err)
 	}
-	if dbPkg.Name == pkg.Name && dbPkg.Version == pkg.Version {
-		log.Infof("package %s version %s is already installed", pkg.Name, pkg.Version)
+	if !shouldInstallPredicate(dbPkg, pkg) {
 		return nil
 	}
 	err = i.preparePackage(ctx, pkg.Name, args) // Preinst