diff --git a/internal/elasticsearch/client.go b/internal/elasticsearch/client.go
index 74cf73d528..2e888d7c79 100644
--- a/internal/elasticsearch/client.go
+++ b/internal/elasticsearch/client.go
@@ -196,7 +196,7 @@ type Info struct {
 	Version     struct {
 		Number      string `json:"number"`
 		BuildFlavor string `json:"build_flavor"`
-	} `json:"version`
+	} `json:"version"`
 }
 
 // Info gets cluster information and metadata.
diff --git a/internal/kibana/packages.go b/internal/kibana/packages.go
index 34fcf7a079..3b8950249e 100644
--- a/internal/kibana/packages.go
+++ b/internal/kibana/packages.go
@@ -7,6 +7,7 @@ package kibana
 import (
 	"context"
 	"encoding/json"
+	"errors"
 	"fmt"
 	"net/http"
 	"os"
@@ -14,6 +15,8 @@ import (
 	"github.com/elastic/elastic-package/internal/packages"
 )
 
+var ErrNotSupported error = errors.New("not supported")
+
 // InstallPackage installs the given package in Fleet.
 func (c *Client) InstallPackage(ctx context.Context, name, version string) ([]packages.Asset, error) {
 	path := c.epmPackageUrl(name, version)
@@ -27,6 +30,47 @@ func (c *Client) InstallPackage(ctx context.Context, name, version string) ([]pa
 	return processResults("install", statusCode, respBody)
 }
 
+// EnsureZipPackageCanBeInstalled checks whether or not it can be installed a package using the upload API.
+// This is intened to be used between 8.7.0 and 8.8.2 stack versions, and it is only safe to be run in those
+// stack versions.
+func (c *Client) EnsureZipPackageCanBeInstalled(ctx context.Context) error {
+	path := fmt.Sprintf("%s/epm/packages", FleetAPI)
+
+	req, err := c.newRequest(ctx, http.MethodPost, path, nil)
+	if err != nil {
+		return err
+	}
+	req.Header.Set("Content-Type", "application/zip")
+	req.Header.Add("elastic-api-version", "2023-10-31")
+
+	statusCode, respBody, err := c.doRequest(req)
+	if err != nil {
+		return fmt.Errorf("could not install zip package: %w", err)
+	}
+	switch statusCode {
+	case http.StatusBadRequest:
+		// If the stack allows to use the upload API, the response is like this one:
+		// {
+		//   "statusCode":400,
+		//   "error":"Bad Request",
+		//   "message":"Error during extraction of package: Error: end of central directory record signature not found. Assumed content type was application/zip, check if this matches the archive type."
+		// }
+		return nil
+	case http.StatusForbidden:
+		var resp struct {
+			Message string `json:"message"`
+		}
+		if err := json.Unmarshal(respBody, &resp); err != nil {
+			return fmt.Errorf("could not unmarhsall response to JSON: %w", err)
+		}
+		if resp.Message == "Requires Enterprise license" {
+			return ErrNotSupported
+		}
+	}
+
+	return fmt.Errorf("unexpected response (status code %d): %s", statusCode, string(respBody))
+}
+
 // InstallZipPackage installs the local zip package in Fleet.
 func (c *Client) InstallZipPackage(ctx context.Context, zipFile string) ([]packages.Asset, error) {
 	path := fmt.Sprintf("%s/epm/packages", FleetAPI)
diff --git a/internal/packages/installer/factory.go b/internal/packages/installer/factory.go
index 29819f43a0..dfcacfbae3 100644
--- a/internal/packages/installer/factory.go
+++ b/internal/packages/installer/factory.go
@@ -18,7 +18,10 @@ import (
 	"github.com/elastic/elastic-package/internal/validation"
 )
 
-var semver8_7_0 = semver.MustParse("8.7.0")
+var (
+	semver8_7_0 = semver.MustParse("8.7.0")
+	semver8_8_2 = semver.MustParse("8.8.2")
+)
 
 // Installer is responsible for installation/uninstallation of the package.
 type Installer interface {
@@ -54,11 +57,15 @@ func NewForPackage(options Options) (Installer, error) {
 		return nil, fmt.Errorf("failed to get kibana version: %w", err)
 	}
 
-	supportsZip := !version.LessThan(semver8_7_0)
+	supportsUploadZip, reason, err := isAllowedInstallationViaApi(context.TODO(), options.Kibana, version)
+	if err != nil {
+		return nil, fmt.Errorf("failed to validate whether or not it can be used upload API: %w", err)
+	}
 	if options.ZipPath != "" {
-		if !supportsZip {
-			return nil, fmt.Errorf("not supported uploading zip packages in Kibana %s (%s required)", version, semver8_7_0)
+		if !supportsUploadZip {
+			return nil, errors.New(reason)
 		}
+
 		if !options.SkipValidation {
 			logger.Debugf("Validating built .zip package (path: %s)", options.ZipPath)
 			errs, skipped := validation.ValidateAndFilterFromZip(options.ZipPath)
@@ -75,7 +82,7 @@ func NewForPackage(options Options) (Installer, error) {
 
 	target, err := builder.BuildPackage(builder.BuildOptions{
 		PackageRoot:    options.RootPath,
-		CreateZip:      supportsZip,
+		CreateZip:      supportsUploadZip,
 		SignPackage:    false,
 		SkipValidation: options.SkipValidation,
 	})
@@ -83,12 +90,33 @@ func NewForPackage(options Options) (Installer, error) {
 		return nil, fmt.Errorf("failed to build package: %v", err)
 	}
 
-	if supportsZip {
+	if supportsUploadZip {
 		return CreateForZip(options.Kibana, target)
 	}
 	return CreateForManifest(options.Kibana, target)
 }
 
+func isAllowedInstallationViaApi(ctx context.Context, kbnClient *kibana.Client, kibanaVersion *semver.Version) (bool, string, error) {
+	reason := ""
+	if kibanaVersion.LessThan(semver8_7_0) {
+		reason = fmt.Sprintf("not supported uploading zip packages in Kibana %s (%s required)", kibanaVersion, semver8_7_0)
+		return false, reason, nil
+	}
+
+	if kibanaVersion.LessThan(semver8_8_2) {
+		err := kbnClient.EnsureZipPackageCanBeInstalled(ctx)
+		if errors.Is(err, kibana.ErrNotSupported) {
+			reason = fmt.Sprintf("not supported uploading zip packages in Kibana %s (%s required or Enteprise license)", kibanaVersion, semver8_8_2)
+			return false, reason, nil
+		}
+		if err != nil {
+			return false, "", err
+		}
+	}
+
+	return true, "", nil
+}
+
 func kibanaVersion(kibana *kibana.Client) (*semver.Version, error) {
 	version, err := kibana.Version()
 	if err != nil {