diff --git a/cli/internal/cmd/BUILD.bazel b/cli/internal/cmd/BUILD.bazel
index 446561891..3340734c6 100644
--- a/cli/internal/cmd/BUILD.bazel
+++ b/cli/internal/cmd/BUILD.bazel
@@ -40,6 +40,7 @@ go_library(
         "//bootstrapper/initproto",
         "//cli/internal/cloudcmd",
         "//cli/internal/clusterid",
+        "//cli/internal/featureset",
         "//cli/internal/helm",
         "//cli/internal/iamid",
         "//cli/internal/kubernetes",
diff --git a/cli/internal/cmd/configfetchmeasurements.go b/cli/internal/cmd/configfetchmeasurements.go
index 1c796a03e..0fc98984d 100644
--- a/cli/internal/cmd/configfetchmeasurements.go
+++ b/cli/internal/cmd/configfetchmeasurements.go
@@ -14,10 +14,10 @@ import (
 	"net/url"
 	"time"
 
+	"github.com/edgelesssys/constellation/v2/cli/internal/featureset"
 	"github.com/edgelesssys/constellation/v2/internal/api/versionsapi"
 	"github.com/edgelesssys/constellation/v2/internal/attestation/measurements"
 	"github.com/edgelesssys/constellation/v2/internal/config"
-	"github.com/edgelesssys/constellation/v2/internal/constants"
 	"github.com/edgelesssys/constellation/v2/internal/file"
 	"github.com/edgelesssys/constellation/v2/internal/sigstore"
 	"github.com/spf13/afero"
@@ -47,7 +47,8 @@ type fetchMeasurementsFlags struct {
 }
 
 type configFetchMeasurementsCmd struct {
-	log debugLog
+	canFetchMeasurements bool
+	log                  debugLog
 }
 
 func runConfigFetchMeasurements(cmd *cobra.Command, _ []string) error {
@@ -61,7 +62,7 @@ func runConfigFetchMeasurements(cmd *cobra.Command, _ []string) error {
 	if err != nil {
 		return fmt.Errorf("constructing Rekor client: %w", err)
 	}
-	cfm := &configFetchMeasurementsCmd{log: log}
+	cfm := &configFetchMeasurementsCmd{log: log, canFetchMeasurements: featureset.CanFetchMeasurements}
 
 	return cfm.configFetchMeasurements(cmd, sigstore.CosignVerifier{}, rekor, fileHandler, http.DefaultClient)
 }
@@ -76,6 +77,11 @@ func (cfm *configFetchMeasurementsCmd) configFetchMeasurements(
 	}
 	cfm.log.Debugf("Using flags %v", flags)
 
+	if !cfm.canFetchMeasurements {
+		cmd.PrintErrln("Fetching measurements is not supported in the OSS build of the Constellation CLI. Consult the documentation for instructions on where to download the enterprise version.")
+		return errors.New("fetching measurements is not supported")
+	}
+
 	cfm.log.Debugf("Loading configuration file from %q", flags.configPath)
 	conf, err := config.NewWithClient(fileHandler, flags.configPath, client, flags.force)
 	var configValidationErr *config.ValidationError
diff --git a/cli/internal/cmd/configfetchmeasurements_test.go b/cli/internal/cmd/configfetchmeasurements_test.go
index 952f09eee..1a5f35d1f 100644
--- a/cli/internal/cmd/configfetchmeasurements_test.go
+++ b/cli/internal/cmd/configfetchmeasurements_test.go
@@ -277,7 +277,7 @@ func TestConfigFetchMeasurements(t *testing.T) {
 
 			err := fileHandler.WriteYAML(constants.ConfigFilename, gcpConfig, file.OptMkdirAll)
 			require.NoError(err)
-			cfm := &configFetchMeasurementsCmd{log: logger.NewTest(t)}
+			cfm := &configFetchMeasurementsCmd{canFetchMeasurements: true, log: logger.NewTest(t)}
 
 			err = cfm.configFetchMeasurements(cmd, tc.cosign, tc.rekor, fileHandler, client)
 			if tc.wantErr {
diff --git a/cli/internal/cmd/upgradecheck.go b/cli/internal/cmd/upgradecheck.go
index c48554bc5..5f6d539d1 100644
--- a/cli/internal/cmd/upgradecheck.go
+++ b/cli/internal/cmd/upgradecheck.go
@@ -15,6 +15,7 @@ import (
 	"sort"
 	"strings"
 
+	"github.com/edgelesssys/constellation/v2/cli/internal/featureset"
 	"github.com/edgelesssys/constellation/v2/cli/internal/helm"
 	"github.com/edgelesssys/constellation/v2/cli/internal/kubernetes"
 	"github.com/edgelesssys/constellation/v2/internal/api/fetcher"
@@ -73,6 +74,7 @@ func runUpgradeCheck(cmd *cobra.Command, _ []string) error {
 		return fmt.Errorf("constructing Rekor client: %w", err)
 	}
 	up := &upgradeCheckCmd{
+		canUpgradeCheck: featureset.CanUpgradeCheck,
 		collect: &versionCollector{
 			writer:         cmd.OutOrStderr(),
 			checker:        checker,
@@ -123,8 +125,9 @@ func parseUpgradeCheckFlags(cmd *cobra.Command) (upgradeCheckFlags, error) {
 }
 
 type upgradeCheckCmd struct {
-	collect collector
-	log     debugLog
+	canUpgradeCheck bool
+	collect         collector
+	log             debugLog
 }
 
 // upgradePlan plans an upgrade of a Constellation cluster.
@@ -138,6 +141,12 @@ func (u *upgradeCheckCmd) upgradeCheck(cmd *cobra.Command, fileHandler file.Hand
 		return err
 	}
 	u.log.Debugf("Read configuration from %q", flags.configPath)
+
+	if !u.canUpgradeCheck {
+		cmd.PrintErrln("Planning Constellation upgrades automatically is not supported in the OSS build of the Constellation CLI. Consult the documentation for instructions on where to download the enterprise version.")
+		return errors.New("upgrade check is not supported")
+	}
+
 	// get current image version of the cluster
 	csp := conf.GetProvider()
 	attestationVariant := conf.GetAttestationConfig().GetVariant()
diff --git a/cli/internal/cmd/upgradecheck_test.go b/cli/internal/cmd/upgradecheck_test.go
index 5663d55ec..47d02a4de 100644
--- a/cli/internal/cmd/upgradecheck_test.go
+++ b/cli/internal/cmd/upgradecheck_test.go
@@ -264,8 +264,9 @@ func TestUpgradeCheck(t *testing.T) {
 			require.NoError(fileHandler.WriteYAML(tc.flags.configPath, cfg))
 
 			checkCmd := upgradeCheckCmd{
-				collect: &tc.collector,
-				log:     logger.NewTest(t),
+				canUpgradeCheck: true,
+				collect:         &tc.collector,
+				log:             logger.NewTest(t),
 			}
 
 			cmd := newUpgradeCheckCmd()
diff --git a/cli/internal/featureset/BUILD.bazel b/cli/internal/featureset/BUILD.bazel
new file mode 100644
index 000000000..17e2db12a
--- /dev/null
+++ b/cli/internal/featureset/BUILD.bazel
@@ -0,0 +1,14 @@
+load("@io_bazel_rules_go//go:def.bzl", "go_library")
+
+go_library(
+    name = "featureset",
+    srcs = [
+        "featureset.go",
+        # keep
+        "featureset_enterprise.go",
+        # keep
+        "featureset_oss.go",
+    ],
+    importpath = "github.com/edgelesssys/constellation/v2/cli/internal/featureset",
+    visibility = ["//cli:__subpackages__"],
+)
diff --git a/cli/internal/featureset/featureset.go b/cli/internal/featureset/featureset.go
new file mode 100644
index 000000000..ae0c9f050
--- /dev/null
+++ b/cli/internal/featureset/featureset.go
@@ -0,0 +1,28 @@
+/*
+Copyright (c) Edgeless Systems GmbH
+
+SPDX-License-Identifier: AGPL-3.0-only
+*/
+
+// package featureset provides a way to check whether a feature is enabled in the current build.
+package featureset
+
+// Edition is the edition of a build.
+type Edition int
+
+const (
+	// EditionOSS is the open-source software edition.
+	EditionOSS Edition = iota
+	// EditionEnterprise is the enterprise edition.
+	EditionEnterprise
+)
+
+// CanFetchMeasurements returns whether the current build can fetch measurements.
+const CanFetchMeasurements = canFetchMeasurements
+
+// CanUpgradeCheck returns whether the current build can check for upgrades.
+// This also includes fetching new measurements.
+const CanUpgradeCheck = canUpgradeCheck
+
+// CurrentEdition is the edition of the current build.
+const CurrentEdition = edition
diff --git a/cli/internal/featureset/featureset_enterprise.go b/cli/internal/featureset/featureset_enterprise.go
new file mode 100644
index 000000000..cb1b0157f
--- /dev/null
+++ b/cli/internal/featureset/featureset_enterprise.go
@@ -0,0 +1,15 @@
+//go:build enterprise
+
+/*
+Copyright (c) Edgeless Systems GmbH
+
+SPDX-License-Identifier: AGPL-3.0-only
+*/
+
+package featureset
+
+const (
+	edition              = EditionEnterprise
+	canFetchMeasurements = true
+	canUpgradeCheck      = true
+)
diff --git a/cli/internal/featureset/featureset_oss.go b/cli/internal/featureset/featureset_oss.go
new file mode 100644
index 000000000..426be123f
--- /dev/null
+++ b/cli/internal/featureset/featureset_oss.go
@@ -0,0 +1,15 @@
+//go:build !enterprise
+
+/*
+Copyright (c) Edgeless Systems GmbH
+
+SPDX-License-Identifier: AGPL-3.0-only
+*/
+
+package featureset
+
+const (
+	edition              = EditionOSS
+	canFetchMeasurements = false
+	canUpgradeCheck      = false
+)