diff --git a/changelog/fragments/1694190260-improve-upgrade-logging.yaml b/changelog/fragments/1694190260-improve-upgrade-logging.yaml
new file mode 100644
index 00000000000..a471629b90a
--- /dev/null
+++ b/changelog/fragments/1694190260-improve-upgrade-logging.yaml
@@ -0,0 +1,32 @@
+# Kind can be one of:
+# - breaking-change: a change to previously-documented behavior
+# - deprecation: functionality that is being removed in a later release
+# - bug-fix: fixes a problem in a previous version
+# - enhancement: extends functionality but does not break or fix existing behavior
+# - feature: new functionality
+# - known-issue: problems that we are aware of in a given version
+# - security: impacts on the security of a product or a user’s deployment.
+# - upgrade: important information for someone upgrading from a prior version
+# - other: does not fit into any of the other categories
+kind: enhancement
+
+# Change summary; a 80ish characters long description of the change.
+summary: Improve logging during Agent upgrades
+
+# Long description; in case the summary is not enough to describe the change
+# this field accommodate a description without length limits.
+# NOTE: This field will be rendered only for breaking-change and known-issue kinds at the moment.
+#description:
+
+# Affected component; usually one of "elastic-agent", "fleet-server", "filebeat", "metricbeat", "auditbeat", "all", etc.
+component: elastic-agent
+
+# PR URL; optional; the PR number that added the changeset.
+# If not present is automatically filled by the tooling finding the PR where this changelog fragment has been added.
+# NOTE: the tooling supports backports, so it's able to fill the original PR number instead of the backport PR number.
+# Please provide it if you are adding a fragment for a different PR.
+pr: https://github.com/elastic/elastic-agent/pull/3382
+
+# Issue URL; optional; the GitHub issue related to this changeset (either closes or is part of).
+# If not present is automatically filled by the tooling with the issue linked to the PR number.
+#issue: https://github.com/owner/repo/1234
diff --git a/internal/pkg/agent/application/upgrade/cleanup.go b/internal/pkg/agent/application/upgrade/cleanup.go
index 4464a1d8f70..cc6bacf4635 100644
--- a/internal/pkg/agent/application/upgrade/cleanup.go
+++ b/internal/pkg/agent/application/upgrade/cleanup.go
@@ -19,7 +19,7 @@ import (
 // cleanNonMatchingVersionsFromDownloads will remove files that do not have the passed version number from the downloads directory.
 func cleanNonMatchingVersionsFromDownloads(log *logger.Logger, version string) error {
 	downloadsPath := paths.Downloads()
-	log.Debugw("Cleaning up non-matching downloaded versions", "version", version, "downloads.path", downloadsPath)
+	log.Infow("Cleaning up non-matching downloaded versions", "version", version, "downloads.path", downloadsPath)
 
 	files, err := os.ReadDir(downloadsPath)
 	if os.IsNotExist(err) {
diff --git a/internal/pkg/agent/application/upgrade/crash_checker.go b/internal/pkg/agent/application/upgrade/crash_checker.go
index fd6016208e0..67bc2bf862c 100644
--- a/internal/pkg/agent/application/upgrade/crash_checker.go
+++ b/internal/pkg/agent/application/upgrade/crash_checker.go
@@ -7,7 +7,6 @@ package upgrade
 import (
 	"context"
 	"fmt"
-	"os"
 	"sync"
 	"time"
 
@@ -53,7 +52,7 @@ func NewCrashChecker(ctx context.Context, ch chan error, log *logger.Logger, che
 		return nil, err
 	}
 
-	log.Debugf("running checks using '%s' controller", c.sc.Name())
+	log.Infof("running checks using '%s' controller", c.sc.Name())
 
 	return c, nil
 }
@@ -62,9 +61,8 @@ func NewCrashChecker(ctx context.Context, ch chan error, log *logger.Logger, che
 func (ch *CrashChecker) Run(ctx context.Context) {
 	defer ch.sc.Close()
 
-	ch.log.Debug("Crash checker started")
+	ch.log.Info("Crash checker started")
 	for {
-		ch.log.Debugf("watcher having PID: %d", os.Getpid())
 		t := time.NewTimer(ch.checkInterval)
 
 		select {
@@ -77,7 +75,7 @@ func (ch *CrashChecker) Run(ctx context.Context) {
 				ch.log.Error(err)
 			}
 
-			ch.log.Debugf("retrieved service PID [%d]", pid)
+			ch.log.Infof("retrieved service PID [%d]", pid)
 			ch.q.Push(pid)
 
 			// We decide if the Agent process has crashed in either of
diff --git a/internal/pkg/agent/application/upgrade/error_checker.go b/internal/pkg/agent/application/upgrade/error_checker.go
index d6bad9f3e4d..a0a3516c94a 100644
--- a/internal/pkg/agent/application/upgrade/error_checker.go
+++ b/internal/pkg/agent/application/upgrade/error_checker.go
@@ -49,7 +49,7 @@ func NewErrorChecker(ch chan error, log *logger.Logger, checkInterval time.Durat
 
 // Run runs the checking loop.
 func (ch *ErrorChecker) Run(ctx context.Context) {
-	ch.log.Debug("Error checker started")
+	ch.log.Info("Error checker started")
 	for {
 		t := time.NewTimer(ch.checkInterval)
 		select {
diff --git a/internal/pkg/agent/application/upgrade/rollback.go b/internal/pkg/agent/application/upgrade/rollback.go
index ac835cd67e2..ae3c568acf1 100644
--- a/internal/pkg/agent/application/upgrade/rollback.go
+++ b/internal/pkg/agent/application/upgrade/rollback.go
@@ -55,7 +55,7 @@ func Rollback(ctx context.Context, log *logger.Logger, prevHash string, currentH
 
 // Cleanup removes all artifacts and files related to a specified version.
 func Cleanup(log *logger.Logger, currentHash string, removeMarker bool, keepLogs bool) error {
-	log.Debugw("Cleaning up upgrade", "hash", currentHash, "remove_marker", removeMarker)
+	log.Infow("Cleaning up upgrade", "hash", currentHash, "remove_marker", removeMarker)
 	<-time.After(afterRestartDelay)
 
 	// remove upgrade marker
@@ -78,7 +78,7 @@ func Cleanup(log *logger.Logger, currentHash string, removeMarker bool, keepLogs
 
 	// remove symlink to avoid upgrade failures, ignore error
 	prevSymlink := prevSymlinkPath()
-	log.Debugw("Removing previous symlink path", "file.path", prevSymlinkPath())
+	log.Infow("Removing previous symlink path", "file.path", prevSymlinkPath())
 	_ = os.Remove(prevSymlink)
 
 	dirPrefix := fmt.Sprintf("%s-", agentName)
@@ -93,7 +93,7 @@ func Cleanup(log *logger.Logger, currentHash string, removeMarker bool, keepLogs
 		}
 
 		hashedDir := filepath.Join(paths.Data(), dir)
-		log.Debugw("Removing hashed data directory", "file.path", hashedDir)
+		log.Infow("Removing hashed data directory", "file.path", hashedDir)
 		var ignoredDirs []string
 		if keepLogs {
 			ignoredDirs = append(ignoredDirs, "logs")
@@ -110,20 +110,28 @@ func Cleanup(log *logger.Logger, currentHash string, removeMarker bool, keepLogs
 // agent during upgrade period.
 func InvokeWatcher(log *logger.Logger) error {
 	if !IsUpgradeable() {
-		log.Debug("agent is not upgradable, not starting watcher")
+		log.Info("agent is not upgradable, not starting watcher")
 		return nil
 	}
 
 	cmd := invokeCmd()
 	defer func() {
 		if cmd.Process != nil {
-			log.Debugf("releasing watcher %v", cmd.Process.Pid)
+			log.Infof("releasing watcher %v", cmd.Process.Pid)
 			_ = cmd.Process.Release()
 		}
 	}()
 
-	log.Debugw("Starting upgrade watcher", "path", cmd.Path, "args", cmd.Args, "env", cmd.Env, "dir", cmd.Dir)
-	return cmd.Start()
+	log.Infow("Starting upgrade watcher", "path", cmd.Path, "args", cmd.Args, "env", cmd.Env, "dir", cmd.Dir)
+	if err := cmd.Start(); err != nil {
+		return fmt.Errorf("failed to start Upgrade Watcher: %w", err)
+	}
+
+	upgradeWatcherPID := cmd.Process.Pid
+	agentPID := os.Getpid()
+	log.Infow("Upgrade Watcher invoked", "agent.upgrade.watcher.process.pid", upgradeWatcherPID, "agent.process.pid", agentPID)
+
+	return nil
 }
 
 func restartAgent(ctx context.Context, log *logger.Logger) error {
diff --git a/internal/pkg/agent/application/upgrade/step_download.go b/internal/pkg/agent/application/upgrade/step_download.go
index 9de9f9ffe13..a1f3bd79ca2 100644
--- a/internal/pkg/agent/application/upgrade/step_download.go
+++ b/internal/pkg/agent/application/upgrade/step_download.go
@@ -54,7 +54,7 @@ func (u *Upgrader) downloadArtifact(ctx context.Context, version, sourceURI stri
 		}
 	}
 
-	u.log.Debugw("Downloading upgrade artifact", "version", version,
+	u.log.Infow("Downloading upgrade artifact", "version", version,
 		"source_uri", settings.SourceURI, "drop_path", settings.DropPath,
 		"target_path", settings.TargetDirectory, "install_path", settings.InstallPath)
 
@@ -162,7 +162,7 @@ func (u *Upgrader) downloadWithRetries(
 
 	opFn := func() error {
 		attempt++
-		u.log.Debugf("download attempt %d", attempt)
+		u.log.Infof("download attempt %d", attempt)
 
 		downloader, err := downloaderCtor(version, u.log, settings)
 		if err != nil {
diff --git a/internal/pkg/agent/application/upgrade/step_mark.go b/internal/pkg/agent/application/upgrade/step_mark.go
index fa337e3907a..0e9cf0bd92a 100644
--- a/internal/pkg/agent/application/upgrade/step_mark.go
+++ b/internal/pkg/agent/application/upgrade/step_mark.go
@@ -139,7 +139,7 @@ func UpdateActiveCommit(log *logger.Logger, hash string) error {
 // CleanMarker removes a marker from disk.
 func CleanMarker(log *logger.Logger) error {
 	markerFile := markerFilePath()
-	log.Debugw("Removing marker file", "file.path", markerFile)
+	log.Infow("Removing marker file", "file.path", markerFile)
 	if err := os.Remove(markerFile); !os.IsNotExist(err) {
 		return err
 	}
diff --git a/internal/pkg/agent/application/upgrade/upgrade.go b/internal/pkg/agent/application/upgrade/upgrade.go
index 13c787ab592..e653cf54525 100644
--- a/internal/pkg/agent/application/upgrade/upgrade.go
+++ b/internal/pkg/agent/application/upgrade/upgrade.go
@@ -11,11 +11,11 @@ import (
 	"path/filepath"
 	"strings"
 
-	"github.com/elastic/elastic-agent/internal/pkg/config"
-
 	"github.com/otiai10/copy"
 	"go.elastic.co/apm"
 
+	"github.com/elastic/elastic-agent/internal/pkg/config"
+
 	"github.com/elastic/elastic-agent/internal/pkg/agent/application/info"
 	"github.com/elastic/elastic-agent/internal/pkg/agent/application/paths"
 	"github.com/elastic/elastic-agent/internal/pkg/agent/application/reexec"
@@ -172,7 +172,7 @@ func (u *Upgrader) Upgrade(ctx context.Context, version string, sourceURI string
 	cb := shutdownCallback(u.log, paths.Home(), release.Version(), version, release.TrimCommit(newHash))
 
 	// Clean everything from the downloads dir
-	u.log.Debugw("Removing downloads directory", "file.path", paths.Downloads())
+	u.log.Infow("Removing downloads directory", "file.path", paths.Downloads())
 	err = os.RemoveAll(paths.Downloads())
 	if err != nil {
 		u.log.Errorw("Unable to clean downloads after update", "error.message", err, "file.path", paths.Downloads())
@@ -231,11 +231,11 @@ func copyActionStore(log *logger.Logger, newHash string) error {
 	// copies legacy action_store.yml, state.yml and state.enc encrypted file if exists
 	storePaths := []string{paths.AgentActionStoreFile(), paths.AgentStateStoreYmlFile(), paths.AgentStateStoreFile()}
 	newHome := filepath.Join(filepath.Dir(paths.Home()), fmt.Sprintf("%s-%s", agentName, newHash))
-	log.Debugw("Copying action store", "new_home_path", newHome)
+	log.Infow("Copying action store", "new_home_path", newHome)
 
 	for _, currentActionStorePath := range storePaths {
 		newActionStorePath := filepath.Join(newHome, filepath.Base(currentActionStorePath))
-		log.Debugw("Copying action store path", "from", currentActionStorePath, "to", newActionStorePath)
+		log.Infow("Copying action store path", "from", currentActionStorePath, "to", newActionStorePath)
 		currentActionStore, err := os.ReadFile(currentActionStorePath)
 		if os.IsNotExist(err) {
 			// nothing to copy
@@ -266,7 +266,7 @@ func copyRunDirectory(log *logger.Logger, newHash string) error {
 	err := copyDir(log, oldRunPath, newRunPath, true)
 	if os.IsNotExist(err) {
 		// nothing to copy, operation ok
-		log.Debugw("Run directory not present", "old_run_path", oldRunPath)
+		log.Infow("Run directory not present", "old_run_path", oldRunPath)
 		return nil
 	}
 	if err != nil {
diff --git a/internal/pkg/agent/cmd/run.go b/internal/pkg/agent/cmd/run.go
index c5cc9f4b315..2ab23dae7c2 100644
--- a/internal/pkg/agent/cmd/run.go
+++ b/internal/pkg/agent/cmd/run.go
@@ -151,6 +151,8 @@ func run(override cfgOverrider, testingMode bool, fleetInitTimeout time.Duration
 		"source": agentName,
 	})
 
+	l.Infow("Elastic Agent started", "process.pid", os.Getpid(), "agent.version", version.GetAgentPackageVersion())
+
 	cfg, err = tryDelayEnroll(ctx, l, cfg, override)
 	if err != nil {
 		err = errors.New(err, "failed to perform delayed enrollment")
diff --git a/internal/pkg/agent/cmd/watch.go b/internal/pkg/agent/cmd/watch.go
index 23009a3366b..f475cf85669 100644
--- a/internal/pkg/agent/cmd/watch.go
+++ b/internal/pkg/agent/cmd/watch.go
@@ -13,6 +13,8 @@ import (
 	"syscall"
 	"time"
 
+	"github.com/elastic/elastic-agent/version"
+
 	"github.com/elastic/elastic-agent/internal/pkg/config"
 
 	"github.com/spf13/cobra"
@@ -62,6 +64,7 @@ func newWatchCommandWithArgs(_ []string, streams *cli.IOStreams) *cobra.Command
 }
 
 func watchCmd(log *logp.Logger, cfg *configuration.Configuration) error {
+	log.Infow("Upgrade Watcher started", "process.pid", os.Getpid(), "agent.version", version.GetAgentPackageVersion())
 	marker, err := upgrade.LoadMarker()
 	if err != nil {
 		log.Error("failed to load marker", err)
@@ -69,14 +72,14 @@ func watchCmd(log *logp.Logger, cfg *configuration.Configuration) error {
 	}
 	if marker == nil {
 		// no marker found we're not in upgrade process
-		log.Debugf("update marker not present at '%s'", paths.Data())
+		log.Infof("update marker not present at '%s'", paths.Data())
 		return nil
 	}
 
 	locker := filelock.NewAppLocker(paths.Top(), watcherLockFile)
 	if err := locker.TryLock(); err != nil {
 		if errors.Is(err, filelock.ErrAppAlreadyRunning) {
-			log.Debugf("exiting, lock already exists")
+			log.Info("exiting, lock already exists")
 			return nil
 		}
 
@@ -89,7 +92,7 @@ func watchCmd(log *logp.Logger, cfg *configuration.Configuration) error {
 
 	isWithinGrace, tilGrace := gracePeriod(marker, cfg.Settings.Upgrade.Watcher.GracePeriod)
 	if !isWithinGrace {
-		log.Debugf("not within grace [updatedOn %v] %v", marker.UpdatedOn.String(), time.Since(marker.UpdatedOn).String())
+		log.Infof("not within grace [updatedOn %v] %v", marker.UpdatedOn.String(), time.Since(marker.UpdatedOn).String())
 		// if it is started outside of upgrade loop
 		// if we're not within grace and marker is still there it might mean
 		// that cleanup was not performed ok, cleanup everything except current version
diff --git a/internal/pkg/agent/install/testblocking/main.go b/internal/pkg/agent/install/testblocking/main.go
new file mode 100644
index 00000000000..adbd771d22d
--- /dev/null
+++ b/internal/pkg/agent/install/testblocking/main.go
@@ -0,0 +1,15 @@
+// Copyright Elasticsearch B.V. and/or licensed to Elasticsearch B.V. under one
+// or more contributor license agreements. Licensed under the Elastic License;
+// you may not use this file except in compliance with the Elastic License.
+
+package main
+
+import (
+	"math"
+	"time"
+)
+
+// Simple program that blocks forever to ensure exes running from a directory on Windows can be removed during uninstall.
+func main() {
+	<-time.After(time.Duration(math.MaxInt64))
+}
diff --git a/internal/pkg/agent/install/uninstall_windows_test.go b/internal/pkg/agent/install/uninstall_windows_test.go
index 31812988b68..e029b471513 100644
--- a/internal/pkg/agent/install/uninstall_windows_test.go
+++ b/internal/pkg/agent/install/uninstall_windows_test.go
@@ -12,37 +12,34 @@ import (
 	"path/filepath"
 	"testing"
 
+	"github.com/otiai10/copy"
 	"github.com/stretchr/testify/require"
 )
 
-const simpleBlockForever = `
-package main
-
-import (
-    "math"
-    "time"
-)
-
-func main() {
-    <-time.After(time.Duration(math.MaxInt64))
-}
-`
-
 func TestRemovePath(t *testing.T) {
-	dir := filepath.Join(t.TempDir(), "subdir")
-	err := os.Mkdir(dir, 0644)
+	var (
+		pkgName    = "testblocking"
+		binaryName = pkgName + ".exe"
+	)
+
+	// Create a temporary directory that we can safely remove. The directory is created as a new
+	// sub-directory. This avoids having Microsoft Defender quarantine the file if it is exec'd from
+	// the default temporary directory.
+	destDir, err := os.MkdirTemp(pkgName, t.Name())
 	require.NoError(t, err)
 
-	src := filepath.Join(dir, "main.go")
-	err = os.WriteFile(src, []byte(simpleBlockForever), 0644)
-	require.NoError(t, err)
+	// Copy the test executable to the new temporary directory.
+	destpath, err := filepath.Abs(filepath.Join(destDir, binaryName))
+	require.NoErrorf(t, err, "failed dest abs %s + %s", destDir, binaryName)
+
+	srcPath, err := filepath.Abs(filepath.Join(pkgName, binaryName))
+	require.NoErrorf(t, err, "failed src abs %s + %s", pkgName, binaryName)
 
-	binary := filepath.Join(dir, "main.exe")
-	cmd := exec.Command("go", "build", "-o", binary, src)
-	_, err = cmd.CombinedOutput()
+	err = copy.Copy(srcPath, destpath, copy.Options{Sync: true})
 	require.NoError(t, err)
 
-	cmd = exec.Command(binary)
+	// Execute the test executable asynchronously.
+	cmd := exec.Command(destpath)
 	err = cmd.Start()
 	require.NoError(t, err)
 	defer func() {
@@ -50,6 +47,7 @@ func TestRemovePath(t *testing.T) {
 		_ = cmd.Wait()
 	}()
 
-	err = RemovePath(dir)
+	// Ensure the directory containing the executable can be removed.
+	err = RemovePath(destDir)
 	require.NoError(t, err)
 }
diff --git a/magefile.go b/magefile.go
index 91d8167d224..3d0e6de1e9e 100644
--- a/magefile.go
+++ b/magefile.go
@@ -256,16 +256,19 @@ func (Build) Clean() {
 // TestBinaries build the required binaries for the test suite.
 func (Build) TestBinaries() error {
 	wd, _ := os.Getwd()
-	p := filepath.Join(wd, "pkg", "component", "fake")
-	for _, name := range []string{"component", "shipper"} {
-		binary := name
+	testBinaryPkgs := []string{
+		filepath.Join(wd, "pkg", "component", "fake", "component"),
+		filepath.Join(wd, "pkg", "component", "fake", "shipper"),
+		filepath.Join(wd, "internal", "pkg", "agent", "install", "testblocking"),
+	}
+	for _, pkg := range testBinaryPkgs {
+		binary := filepath.Base(pkg)
 		if runtime.GOOS == "windows" {
 			binary += ".exe"
 		}
 
-		fakeDir := filepath.Join(p, name)
-		outputName := filepath.Join(fakeDir, binary)
-		err := RunGo("build", "-o", outputName, filepath.Join(fakeDir))
+		outputName := filepath.Join(pkg, binary)
+		err := RunGo("build", "-o", outputName, filepath.Join(pkg))
 		if err != nil {
 			return err
 		}