diff --git a/changelog/fragments/1693403216-Surface-errors-during-Agent's-enroll.yaml b/changelog/fragments/1693403216-Surface-errors-during-Agent's-enroll.yaml
new file mode 100644
index 00000000000..f8361f99433
--- /dev/null
+++ b/changelog/fragments/1693403216-Surface-errors-during-Agent's-enroll.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: bug-fix
+
+# Change summary; a 80ish characters long description of the change.
+summary: Surface errors during Agent's enroll process, failing if any happens.
+
+# 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; a word indicating the component this changeset affects.
+component: install/enroll
+
+# 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/3207
+
+# 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/dev-tools/mage/godaemon.go b/dev-tools/mage/godaemon.go
index 90960bfe69f..40d5e94564b 100644
--- a/dev-tools/mage/godaemon.go
+++ b/dev-tools/mage/godaemon.go
@@ -21,7 +21,7 @@ var (
 	}
 )
 
-// BuildGoDaemon builds the go-deamon binary.
+// BuildGoDaemon builds the go-daemon binary.
 func BuildGoDaemon() error {
 	if GOOS != "linux" {
 		return errors.New("go-daemon only builds for linux")
diff --git a/internal/pkg/agent/cmd/enroll.go b/internal/pkg/agent/cmd/enroll.go
index 1bce5f7e547..adaa278f32f 100644
--- a/internal/pkg/agent/cmd/enroll.go
+++ b/internal/pkg/agent/cmd/enroll.go
@@ -351,7 +351,7 @@ func enroll(streams *cli.IOStreams, cmd *cobra.Command) error {
 	//  Error: failed to fix permissions: chown /Library/Elastic/Agent/data/elastic-agent-c13f91/elastic-agent.app: operation not permitted
 	// This is because we are fixing permissions twice, once during installation and again during the enrollment step.
 	// When we are enrolling as part of installation on MacOS, skip the second attempt to fix permissions.
-	var fixPermissions bool = fromInstall
+	fixPermissions := fromInstall
 	if runtime.GOOS == "darwin" {
 		fixPermissions = false
 	}
diff --git a/internal/pkg/agent/cmd/enroll_cmd.go b/internal/pkg/agent/cmd/enroll_cmd.go
index 153c488e37a..f72183c9745 100644
--- a/internal/pkg/agent/cmd/enroll_cmd.go
+++ b/internal/pkg/agent/cmd/enroll_cmd.go
@@ -189,7 +189,7 @@ func newEnrollCmd(
 	)
 }
 
-// newEnrollCmdWithStore creates an new enrollment and accept a custom store.
+// newEnrollCmdWithStore creates a new enrollment and accept a custom store.
 func newEnrollCmdWithStore(
 	log *logger.Logger,
 	options *enrollCmdOption,
@@ -204,10 +204,11 @@ func newEnrollCmdWithStore(
 	}, nil
 }
 
-// Execute tries to enroll the agent into Fleet.
+// Execute enrolls the agent into Fleet.
 func (c *enrollCmd) Execute(ctx context.Context, streams *cli.IOStreams) error {
 	var err error
 	defer c.stopAgent() // ensure its stopped no matter what
+
 	span, ctx := apm.StartSpan(ctx, "enroll", "app.internal")
 	defer func() {
 		apm.CaptureError(ctx, err).Send()
@@ -252,7 +253,7 @@ func (c *enrollCmd) Execute(ctx context.Context, streams *cli.IOStreams) error {
 		// Ensure that the agent does not use a proxy configuration
 		// when connecting to the local fleet server.
 		// Note that when running fleet-server the enroll request will be sent to :8220,
-		// however when the agent is running afterwards requests will be sent to :8221
+		// however when the agent is running afterward requests will be sent to :8221
 		c.remoteConfig.Transport.Proxy.Disable = true
 	}
 
@@ -273,7 +274,7 @@ func (c *enrollCmd) Execute(ctx context.Context, streams *cli.IOStreams) error {
 
 	err = c.enrollWithBackoff(ctx, persistentConfig)
 	if err != nil {
-		return errors.New(err, "fail to enroll")
+		return fmt.Errorf("fail to enroll: %w", err)
 	}
 
 	if c.options.FixPermissions {
@@ -284,17 +285,23 @@ func (c *enrollCmd) Execute(ctx context.Context, streams *cli.IOStreams) error {
 	}
 
 	defer func() {
-		fmt.Fprintln(streams.Out, "Successfully enrolled the Elastic Agent.")
+		if err != nil {
+			fmt.Fprintf(streams.Err, "Something went wrong while enrolling the Elastic Agent: %v\n", err)
+		} else {
+			fmt.Fprintln(streams.Out, "Successfully enrolled the Elastic Agent.")
+		}
 	}()
 
 	if c.agentProc == nil {
-		if err := c.daemonReload(ctx); err != nil {
-			c.log.Infow("Elastic Agent might not be running; unable to trigger restart", "error", err)
-		} else {
-			c.log.Info("Successfully triggered restart on running Elastic Agent.")
+		if err = c.daemonReloadWithBackoff(ctx); err != nil {
+			c.log.Errorf("Elastic Agent might not be running; unable to trigger restart: %v", err)
+			return fmt.Errorf("could not reload agent daemon, unable to trigger restart: %w", err)
 		}
+
+		c.log.Info("Successfully triggered restart on running Elastic Agent.")
 		return nil
 	}
+
 	c.log.Info("Elastic Agent has been enrolled; start Elastic Agent")
 	return nil
 }
@@ -460,24 +467,35 @@ func (c *enrollCmd) prepareFleetTLS() error {
 
 func (c *enrollCmd) daemonReloadWithBackoff(ctx context.Context) error {
 	err := c.daemonReload(ctx)
+	if err != nil &&
+		(errors.Is(err, context.DeadlineExceeded) ||
+			errors.Is(err, context.Canceled)) {
+		return fmt.Errorf("could not reload daemon: %w", err)
+	}
 	if err == nil {
 		return nil
 	}
 
 	signal := make(chan struct{})
+	defer close(signal)
 	backExp := backoff.NewExpBackoff(signal, 10*time.Second, 1*time.Minute)
 
-	for i := 5; i >= 0; i-- {
+	for i := 0; i < 5; i++ {
 		backExp.Wait()
 		c.log.Info("Retrying to restart...")
 		err = c.daemonReload(ctx)
+		if err != nil &&
+			(errors.Is(err, context.DeadlineExceeded) ||
+				errors.Is(err, context.Canceled)) {
+			return fmt.Errorf("could not reload daemon after %d retries: %w",
+				i+1, err)
+		}
 		if err == nil {
-			break
+			return nil
 		}
 	}
 
-	close(signal)
-	return err
+	return fmt.Errorf("could not reload agent's daemon, all retries failed. Last error: %w", err)
 }
 
 func (c *enrollCmd) daemonReload(ctx context.Context) (err error) {
@@ -501,8 +519,20 @@ func (c *enrollCmd) enrollWithBackoff(ctx context.Context, persistentConfig map[
 
 	c.log.Infof("Starting enrollment to URL: %s", c.client.URI())
 	err := c.enroll(ctx, persistentConfig)
+	if err == nil {
+		return nil
+	}
+
+	const deadline = 10 * time.Minute
+	const frequency = 60 * time.Second
+
+	c.log.Infof("1st enrollment attempt failed, retrying for %s, every %s enrolling to URL: %s",
+		deadline,
+		frequency,
+		c.client.URI())
 	signal := make(chan struct{})
-	backExp := backoff.NewExpBackoff(signal, 60*time.Second, 10*time.Minute)
+	defer close(signal)
+	backExp := backoff.NewExpBackoff(signal, frequency, deadline)
 
 	for {
 		retry := false
@@ -521,7 +551,6 @@ func (c *enrollCmd) enrollWithBackoff(ctx context.Context, persistentConfig map[
 		err = c.enroll(ctx, persistentConfig)
 	}
 
-	close(signal)
 	return err
 }
 
@@ -570,8 +599,10 @@ func (c *enrollCmd) enroll(ctx context.Context, persistentConfig map[string]inte
 			c.options.FleetServer.ElasticsearchInsecure,
 		)
 		if err != nil {
-			return err
+			return fmt.Errorf(
+				"failed creating fleet-server bootstrap config: %w", err)
 		}
+
 		// no longer need bootstrap at this point
 		serverConfig.Server.Bootstrap = false
 		fleetConfig.Server = serverConfig.Server
@@ -591,11 +622,11 @@ func (c *enrollCmd) enroll(ctx context.Context, persistentConfig map[string]inte
 
 	reader, err := yamlToReader(configToStore)
 	if err != nil {
-		return err
+		return fmt.Errorf("yamlToReader failed: %w", err)
 	}
 
 	if err := safelyStoreAgentInfo(c.configStore, reader); err != nil {
-		return err
+		return fmt.Errorf("failed to store agent config: %w", err)
 	}
 
 	// clear action store
diff --git a/internal/pkg/agent/cmd/enroll_cmd_test.go b/internal/pkg/agent/cmd/enroll_cmd_test.go
index d34bf200148..ca62f82024d 100644
--- a/internal/pkg/agent/cmd/enroll_cmd_test.go
+++ b/internal/pkg/agent/cmd/enroll_cmd_test.go
@@ -17,8 +17,11 @@ import (
 	"os"
 	"runtime"
 	"strconv"
+	"strings"
 	"testing"
+	"time"
 
+	"github.com/stretchr/testify/assert"
 	"github.com/stretchr/testify/require"
 
 	"github.com/elastic/elastic-agent/internal/pkg/agent/configuration"
@@ -160,14 +163,23 @@ func TestEnroll(t *testing.T) {
 			require.NoError(t, err)
 
 			streams, _, _, _ := cli.NewTestingIOStreams()
-			err = cmd.Execute(context.Background(), streams)
-			require.NoError(t, err)
-
+			ctx, cancel := context.WithTimeout(context.Background(), 1*time.Minute)
+			defer cancel()
+			err = cmd.Execute(ctx, streams)
+
+			// There is no agent running, therefore nothing to be restarted.
+			// However, this will cause the Enroll command to return an error
+			// which we'll ignore here.
+			require.ErrorContainsf(t, err,
+				"could not reload agent daemon, unable to trigger restart",
+				"enroll command returned an unexpected error")
+			require.ErrorContainsf(t, err, context.DeadlineExceeded.Error(),
+				"it should fail only due to %q", context.DeadlineExceeded)
 			config, err := readConfig(store.Content)
-
 			require.NoError(t, err)
-			require.Equal(t, "my-access-api-key", config.AccessAPIKey)
-			require.Equal(t, host, config.Client.Host)
+
+			assert.Equal(t, "my-access-api-key", config.AccessAPIKey)
+			assert.Equal(t, host, config.Client.Host)
 		},
 	))
 
@@ -217,16 +229,24 @@ func TestEnroll(t *testing.T) {
 			require.NoError(t, err)
 
 			streams, _, _, _ := cli.NewTestingIOStreams()
-			err = cmd.Execute(context.Background(), streams)
-			require.NoError(t, err)
-
-			require.True(t, store.Called)
-
+			ctx, cancel := context.WithTimeout(context.Background(), 1*time.Minute)
+			defer cancel()
+			err = cmd.Execute(ctx, streams)
+			if err != nil &&
+				// There is no agent running, therefore nothing to be restarted.
+				// However, this will cause the Enroll command to return an error
+				// which we'll ignore here.
+				!strings.Contains(err.Error(),
+					"could not reload agent daemon, unable to trigger restart") {
+				t.Fatalf("enrrol coms returned and unexpected error: %v", err)
+			}
+
+			assert.True(t, store.Called)
 			config, err := readConfig(store.Content)
 
-			require.NoError(t, err)
-			require.Equal(t, "my-access-api-key", config.AccessAPIKey)
-			require.Equal(t, host, config.Client.Host)
+			assert.NoError(t, err)
+			assert.Equal(t, "my-access-api-key", config.AccessAPIKey)
+			assert.Equal(t, host, config.Client.Host)
 		},
 	))
 
@@ -276,16 +296,24 @@ func TestEnroll(t *testing.T) {
 			require.NoError(t, err)
 
 			streams, _, _, _ := cli.NewTestingIOStreams()
-			err = cmd.Execute(context.Background(), streams)
-			require.NoError(t, err)
-
-			require.True(t, store.Called)
-
+			ctx, cancel := context.WithTimeout(context.Background(), 1*time.Minute)
+			defer cancel()
+			err = cmd.Execute(ctx, streams)
+
+			if err != nil &&
+				// There is no agent running, therefore nothing to be restarted.
+				// However, this will cause the Enroll command to return an error
+				// which we'll ignore here.
+				!strings.Contains(err.Error(),
+					"could not reload agent daemon, unable to trigger restart") {
+				t.Fatalf("enrrol coms returned and unexpected error: %v", err)
+			}
+
+			assert.True(t, store.Called)
 			config, err := readConfig(store.Content)
-
 			require.NoError(t, err)
-			require.Equal(t, "my-access-api-key", config.AccessAPIKey)
-			require.Equal(t, host, config.Client.Host)
+			assert.Equal(t, "my-access-api-key", config.AccessAPIKey)
+			assert.Equal(t, host, config.Client.Host)
 		},
 	))
 
diff --git a/internal/pkg/agent/cmd/install.go b/internal/pkg/agent/cmd/install.go
index 4fbd37f40da..2cb46bd599d 100644
--- a/internal/pkg/agent/cmd/install.go
+++ b/internal/pkg/agent/cmd/install.go
@@ -154,7 +154,7 @@ func installCmd(streams *cli.IOStreams, cmd *cobra.Command) error {
 				return fmt.Errorf("problem reading prompt response")
 			}
 			if url == "" {
-				fmt.Fprintf(streams.Out, "Enrollment cancelled because no URL was provided.\n")
+				fmt.Fprintln(streams.Out, "Enrollment cancelled because no URL was provided.")
 				return nil
 			}
 		}
@@ -224,6 +224,8 @@ func installCmd(streams *cli.IOStreams, cmd *cobra.Command) error {
 				}
 			}()
 		}
+
+		fmt.Fprintln(streams.Out, "Elastic Agent successfully installed, starting enrollment.")
 	}
 
 	if enroll {
diff --git a/internal/pkg/agent/install/perms_unix.go b/internal/pkg/agent/install/perms_unix.go
index e84dcd5039c..fc357fd4fde 100644
--- a/internal/pkg/agent/install/perms_unix.go
+++ b/internal/pkg/agent/install/perms_unix.go
@@ -8,6 +8,7 @@ package install
 
 import (
 	"errors"
+	"fmt"
 	"io/fs"
 	"os"
 	"path/filepath"
@@ -18,19 +19,26 @@ func fixPermissions(topPath string) error {
 	return recursiveRootPermissions(topPath)
 }
 
-func recursiveRootPermissions(path string) error {
-	return filepath.Walk(path, func(name string, info fs.FileInfo, err error) error {
-		if err == nil {
-			// all files should be owned by root:root
-			err = os.Chown(name, 0, 0)
-			if err != nil {
-				return err
-			}
-			// remove any world permissions from the file
-			err = os.Chmod(name, info.Mode().Perm()&0770)
-		} else if errors.Is(err, fs.ErrNotExist) {
+func recursiveRootPermissions(root string) error {
+	return filepath.Walk(root, func(path string, info fs.FileInfo, err error) error {
+		if errors.Is(err, fs.ErrNotExist) {
 			return nil
 		}
-		return err
+		if err != nil {
+			return fmt.Errorf("walk on %q failed: %w", path, err)
+		}
+
+		// all files should be owned by root:root
+		err = os.Chown(path, 0, 0)
+		if err != nil {
+			return fmt.Errorf("could not fix ownership of %q: %w", path, err)
+		}
+		// remove any world permissions from the file
+		err = os.Chmod(path, info.Mode().Perm()&0770)
+		if err != nil {
+			return fmt.Errorf("could not fix permissions of %q: %w", path, err)
+		}
+
+		return nil
 	})
 }