diff --git a/CHANGELOG.next.asciidoc b/CHANGELOG.next.asciidoc
new file mode 100644
index 000000000..e87170eec
--- /dev/null
+++ b/CHANGELOG.next.asciidoc
@@ -0,0 +1,3 @@
+==== Bugfixes
+
+- Return a better error on enrolling and the Elasticsearch version is incompatible. {pull}1211[1211]
diff --git a/cmd/fleet/main.go b/cmd/fleet/main.go
index 8eeaaa104..7858086c4 100644
--- a/cmd/fleet/main.go
+++ b/cmd/fleet/main.go
@@ -15,11 +15,12 @@ import (
 	"sync"
 	"time"
 
-	"github.com/elastic/go-ucfg"
-	"github.com/elastic/go-ucfg/yaml"
 	"go.elastic.co/apm"
 	apmtransport "go.elastic.co/apm/transport"
 
+	"github.com/elastic/go-ucfg"
+	"github.com/elastic/go-ucfg/yaml"
+
 	"github.com/elastic/fleet-server/v7/internal/pkg/action"
 	"github.com/elastic/fleet-server/v7/internal/pkg/build"
 	"github.com/elastic/fleet-server/v7/internal/pkg/bulk"
@@ -41,14 +42,15 @@ import (
 	"github.com/elastic/fleet-server/v7/internal/pkg/status"
 	"github.com/elastic/fleet-server/v7/internal/pkg/ver"
 
-	"github.com/elastic/elastic-agent-client/v7/pkg/client"
-	"github.com/elastic/elastic-agent-client/v7/pkg/proto"
 	"github.com/hashicorp/go-version"
 	"github.com/pkg/errors"
 	"github.com/rs/zerolog"
 	"github.com/rs/zerolog/log"
 	"github.com/spf13/cobra"
 	"golang.org/x/sync/errgroup"
+
+	"github.com/elastic/elastic-agent-client/v7/pkg/client"
+	"github.com/elastic/elastic-agent-client/v7/pkg/proto"
 )
 
 const (
@@ -785,8 +787,11 @@ func (f *FleetServer) runSubsystems(ctx context.Context, cfg *config.Config, g *
 	esCli := bulker.Client()
 
 	// Check version compatibility with Elasticsearch
-	err = ver.CheckCompatibility(ctx, esCli, f.bi.Version)
+	remoteVersion, err := ver.CheckCompatibility(ctx, esCli, f.bi.Version)
 	if err != nil {
+		if len(remoteVersion) != 0 {
+			return fmt.Errorf("failed version compatibility check with elasticsearch (Agent: %s, Elasticsearch: %s): %w", f.bi.Version, remoteVersion, err)
+		}
 		return fmt.Errorf("failed version compatibility check with elasticsearch: %w", err)
 	}
 
diff --git a/internal/pkg/ver/check.go b/internal/pkg/ver/check.go
index e504bf727..a577f2b4b 100644
--- a/internal/pkg/ver/check.go
+++ b/internal/pkg/ver/check.go
@@ -13,9 +13,10 @@ import (
 
 	esh "github.com/elastic/fleet-server/v7/internal/pkg/es"
 
-	"github.com/elastic/go-elasticsearch/v7"
 	"github.com/hashicorp/go-version"
 	"github.com/rs/zerolog/log"
+
+	"github.com/elastic/go-elasticsearch/v7"
 )
 
 var (
@@ -23,18 +24,18 @@ var (
 	ErrMalformedVersion   = errors.New("malformed version")
 )
 
-func CheckCompatibility(ctx context.Context, esCli *elasticsearch.Client, fleetVersion string) error {
+func CheckCompatibility(ctx context.Context, esCli *elasticsearch.Client, fleetVersion string) (string, error) {
 	log.Debug().Str("fleet_version", fleetVersion).Msg("check version compatibility with elasticsearch")
 
 	esVersion, err := esh.FetchESVersion(ctx, esCli)
 
 	if err != nil {
 		log.Error().Err(err).Msg("failed to fetch elasticsearch version")
-		return err
+		return "", err
 	}
 	log.Debug().Str("elasticsearch_version", esVersion).Msg("fetched elasticsearch version")
 
-	return checkCompatibility(fleetVersion, esVersion)
+	return esVersion, checkCompatibility(fleetVersion, esVersion)
 }
 
 func checkCompatibility(fleetVersion, esVersion string) error {