Fix install/enroll command not failing when the daemon restart fails

changelog/fragments/1700851577-Surface-errors-during-Agent_s-enroll-process-failing-if-any-happens.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; 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/3815/
+
+# 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/elastic/elastic-agent/issues/3664

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")

internal/pkg/agent/cmd/container.go

@@ -397,6 +397,7 @@ func buildEnrollArgs(cfg setupConfig, token string, policyID string) ([]string,
 		"--path.home", paths.Top(), // --path.home actually maps to paths.Top()
 		"--path.config", paths.Config(),
 		"--path.logs", paths.Logs(),
+		"--skip-daemon-reload",
 	}
 	if paths.Downloads() != "" {
 		args = append(args, "--path.downloads", paths.Downloads())

internal/pkg/agent/cmd/enroll.go

@@ -75,7 +75,10 @@ func addEnrollFlags(cmd *cobra.Command) {
 	cmd.Flags().BoolP("delay-enroll", "", false, "Delays enrollment to occur on first start of the Elastic Agent service")
 	cmd.Flags().DurationP("daemon-timeout", "", 0, "Timeout waiting for Elastic Agent daemon")
 	cmd.Flags().DurationP("fleet-server-timeout", "", 0, "Timeout waiting for Fleet Server to be ready to start enrollment")
+	cmd.Flags().Bool("skip-daemon-reload", false, "Skip daemon reload after enrolling")
 	cmd.Flags().StringSliceP("tag", "", []string{}, "User set tags")
+
+	cmd.Flags().MarkHidden("skip-daemon-reload") //nolint:errcheck // an error is only returned if the flag does not exist.
 }
 
 func validateEnrollFlags(cmd *cobra.Command) error {
@@ -141,6 +144,7 @@ func buildEnrollmentFlags(cmd *cobra.Command, url string, token string) []string
 	delayEnroll, _ := cmd.Flags().GetBool("delay-enroll")
 	daemonTimeout, _ := cmd.Flags().GetDuration("daemon-timeout")
 	fTimeout, _ := cmd.Flags().GetDuration("fleet-server-timeout")
+	skipDaemonReload, _ := cmd.Flags().GetBool("skip-daemon-reload")
 	fTags, _ := cmd.Flags().GetStringSlice("tag")
 	args := []string{}
 	if url != "" {
@@ -249,6 +253,9 @@ func buildEnrollmentFlags(cmd *cobra.Command, url string, token string) []string
 		args = append(args, "--fleet-server-es-insecure")
 	}
 
+	if skipDaemonReload {
+		args = append(args, "--skip-daemon-reload")
+	}
 	for _, v := range fTags {
 		args = append(args, "--tag", v)
 	}
@@ -338,6 +345,7 @@ func enroll(streams *cli.IOStreams, cmd *cobra.Command) error {
 	delayEnroll, _ := cmd.Flags().GetBool("delay-enroll")
 	daemonTimeout, _ := cmd.Flags().GetDuration("daemon-timeout")
 	fTimeout, _ := cmd.Flags().GetDuration("fleet-server-timeout")
+	skipDaemonReload, _ := cmd.Flags().GetBool("skip-daemon-reload")
 	tags, _ := cmd.Flags().GetStringSlice("tag")
 
 	caStr, _ := cmd.Flags().GetString("certificate-authorities")
@@ -351,7 +359,7 @@ 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
 	}
@@ -370,6 +378,7 @@ func enroll(streams *cli.IOStreams, cmd *cobra.Command) error {
 		ProxyHeaders:         mapFromEnvList(proxyHeaders),
 		DelayEnroll:          delayEnroll,
 		DaemonTimeout:        daemonTimeout,
+		SkipDaemonRestart:    skipDaemonReload,
 		Tags:                 tags,
 		FleetServer: enrollCmdFleetServerOption{
 			ConnStr:               fServer,

internal/pkg/agent/cmd/enroll_cmd.go

@@ -15,10 +15,6 @@ import (
 	"strings"
 	"time"
 
-	"github.com/elastic/elastic-agent/pkg/utils"
-
-	"github.com/elastic/elastic-agent/pkg/control/v2/client"
-
 	"go.elastic.co/apm"
 	"gopkg.in/yaml.v2"
 
@@ -42,8 +38,10 @@ import (
 	fleetclient "github.com/elastic/elastic-agent/internal/pkg/fleetapi/client"
 	"github.com/elastic/elastic-agent/internal/pkg/release"
 	"github.com/elastic/elastic-agent/internal/pkg/remote"
+	"github.com/elastic/elastic-agent/pkg/control/v2/client"
 	"github.com/elastic/elastic-agent/pkg/core/logger"
 	"github.com/elastic/elastic-agent/pkg/core/process"
+	"github.com/elastic/elastic-agent/pkg/utils"
 )
 
 const (
@@ -115,6 +113,7 @@ type enrollCmdOption struct {
 	DelayEnroll          bool                       `yaml:"-"`
 	FleetServer          enrollCmdFleetServerOption `yaml:"-"`
 	SkipCreateSecret     bool                       `yaml:"-"`
+	SkipDaemonRestart    bool                       `yaml:"-"`
 	Tags                 []string                   `yaml:"omitempty"`
 }
 
@@ -174,7 +173,7 @@ 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,
@@ -189,10 +188,11 @@ 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()
@@ -237,7 +237,7 @@ 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
 	}
 
@@ -258,7 +258,7 @@ 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 {
@@ -269,17 +269,23 @@ 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 c.agentProc == nil && !c.options.SkipDaemonRestart {
+		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
 }
@@ -444,25 +450,34 @@ func (c *enrollCmd) prepareFleetTLS() error {
 }
 
 func (c *enrollCmd) daemonReloadWithBackoff(ctx context.Context) error {
-	err := c.daemonReload(ctx)
-	if err == nil {
-		return nil
-	}
-
 	signal := make(chan struct{})
-	backExp := backoff.NewExpBackoff(signal, 10*time.Second, 1*time.Minute)
+	defer close(signal)
+	backExp := backoff.NewExpBackoff(signal, 1*time.Second, 1*time.Minute)
 
-	for i := 5; i >= 0; i-- {
-		backExp.Wait()
-		c.log.Info("Retrying to restart...")
-		err = c.daemonReload(ctx)
+	var lastErr error
+	for i := 0; i < 5; i++ {
+		attempt := i
+
+		c.log.Infof("Restarting agent daemon, attempt %d", attempt)
+		err := c.daemonReload(ctx)
 		if err == nil {
-			break
+			return nil
 		}
+
+		// If the context was cancelled, return early
+		if errors.Is(err, context.DeadlineExceeded) ||
+			errors.Is(err, context.Canceled) {
+			return fmt.Errorf("could not reload daemon after %d retries: %w",
+				attempt, err)
+		}
+		lastErr = err
+
+		c.log.Errorf("Restart attempt %d failed: '%s'. Waiting for %s", attempt, err, backExp.NextWait().String())
+		backExp.Wait()
+
 	}
 
-	close(signal)
-	return err
+	return fmt.Errorf("could not reload agent's daemon, all retries failed. Last error: %w", lastErr)
 }
 
 func (c *enrollCmd) daemonReload(ctx context.Context) error {
@@ -480,8 +495,20 @@ 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
@@ -500,7 +527,6 @@ func (c *enrollCmd) enrollWithBackoff(ctx context.Context, persistentConfig map[
 		err = c.enroll(ctx, persistentConfig)
 	}
 
-	close(signal)
 	return err
 }
 
@@ -549,8 +575,10 @@ 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
@@ -570,11 +598,11 @@ 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