diff --git a/x-pack/elastic-agent/CHANGELOG.asciidoc b/x-pack/elastic-agent/CHANGELOG.asciidoc
index a5ec2d514b4..e6b764fbc2a 100644
--- a/x-pack/elastic-agent/CHANGELOG.asciidoc
+++ b/x-pack/elastic-agent/CHANGELOG.asciidoc
@@ -86,3 +86,4 @@
 - Configuration cleanup {pull}19848[19848]
 - Agent now sends its own logs to elasticsearch {pull}19811[19811]
 - Add --insecure option to enroll command {pull}19900[19900]
+- Will retry to enroll if the server return a 429. {pull}19918[19811]
diff --git a/x-pack/elastic-agent/pkg/agent/application/fleet_gateway.go b/x-pack/elastic-agent/pkg/agent/application/fleet_gateway.go
index 2856cd83abf..cd94380e673 100644
--- a/x-pack/elastic-agent/pkg/agent/application/fleet_gateway.go
+++ b/x-pack/elastic-agent/pkg/agent/application/fleet_gateway.go
@@ -23,8 +23,8 @@ var defaultGatewaySettings = &fleetGatewaySettings{
 	Duration: 1 * time.Second,        // time between successful calls
 	Jitter:   500 * time.Millisecond, // used as a jitter for duration
 	Backoff: backoffSettings{ // time after a failed call
-		Init: 5 * time.Second,
-		Max:  60 * time.Second,
+		Init: 60 * time.Second,
+		Max:  10 * time.Minute,
 	},
 }
 
diff --git a/x-pack/elastic-agent/pkg/agent/cmd/enroll.go b/x-pack/elastic-agent/pkg/agent/cmd/enroll.go
index 99140951497..c7243926ced 100644
--- a/x-pack/elastic-agent/pkg/agent/cmd/enroll.go
+++ b/x-pack/elastic-agent/pkg/agent/cmd/enroll.go
@@ -12,6 +12,7 @@ import (
 
 	"github.com/spf13/cobra"
 
+	"github.com/elastic/beats/v7/libbeat/common/backoff"
 	c "github.com/elastic/beats/v7/libbeat/common/cli"
 	"github.com/elastic/beats/v7/x-pack/elastic-agent/pkg/agent/application"
 	"github.com/elastic/beats/v7/x-pack/elastic-agent/pkg/agent/configuration"
@@ -20,6 +21,7 @@ import (
 	"github.com/elastic/beats/v7/x-pack/elastic-agent/pkg/cli"
 	"github.com/elastic/beats/v7/x-pack/elastic-agent/pkg/config"
 	"github.com/elastic/beats/v7/x-pack/elastic-agent/pkg/core/logger"
+	"github.com/elastic/beats/v7/x-pack/elastic-agent/pkg/fleetapi"
 )
 
 var defaultDelay = 1 * time.Second
@@ -116,6 +118,19 @@ func enroll(streams *cli.IOStreams, cmd *cobra.Command, flags *globalFlags, args
 	}
 
 	err = c.Execute()
+	signal := make(chan struct{})
+
+	backExp := backoff.NewExpBackoff(signal, 60*time.Second, 10*time.Minute)
+
+	for err == fleetapi.ErrTooManyRequests {
+		fmt.Fprintln(streams.Out, "Too many requests on the remote server, will retry in a moment.")
+		backExp.Wait()
+		fmt.Fprintln(streams.Out, "Retrying to enroll...")
+		err = c.Execute()
+	}
+
+	close(signal)
+
 	if err != nil {
 		return errors.New(err, "fail to enroll")
 	}
diff --git a/x-pack/elastic-agent/pkg/fleetapi/enroll_cmd.go b/x-pack/elastic-agent/pkg/fleetapi/enroll_cmd.go
index 0d2784ef741..55955f3edd5 100644
--- a/x-pack/elastic-agent/pkg/fleetapi/enroll_cmd.go
+++ b/x-pack/elastic-agent/pkg/fleetapi/enroll_cmd.go
@@ -21,6 +21,9 @@ import (
 // EnrollType is the type of enrollment to do with the elastic-agent.
 type EnrollType string
 
+// ErrTooManyRequests is received when the remote server is overloaded.
+var ErrTooManyRequests = errors.New("too many requests received (429)")
+
 const (
 	// PermanentEnroll is default enrollment type, by default an Agent is permanently enroll to Agent.
 	PermanentEnroll = EnrollType("PERMANENT")
@@ -190,6 +193,10 @@ func (e *EnrollCmd) Execute(ctx context.Context, r *EnrollRequest) (*EnrollRespo
 	}
 	defer resp.Body.Close()
 
+	if resp.StatusCode == http.StatusTooManyRequests {
+		return nil, ErrTooManyRequests
+	}
+
 	if resp.StatusCode != http.StatusOK {
 		return nil, extract(resp.Body)
 	}