diff --git a/config/feature_flags.go b/config/feature_flags.go
index bfc93e9893..235a95eb6a 100644
--- a/config/feature_flags.go
+++ b/config/feature_flags.go
@@ -6,6 +6,8 @@ package config
 import (
 	"math"
 	"reflect"
+	"strconv"
+	"strings"
 
 	"github.com/mattermost/mattermost-server/v5/mlog"
 	"github.com/mattermost/mattermost-server/v5/model"
@@ -73,7 +75,8 @@ func (f *FeatureFlagSynchronizer) Close() {
 // featureFlagsFromMap sets the feature flags from a map[string]string.
 // It starts with baseFeatureFlags and only sets values that are
 // given by the upstream management system.
-// Makes the assumption that all feature flags are strings for now.
+// Makes the assumption that all feature flags are strings or booleans.
+// Strings are converted to booleans by considering case insensitive "on" or any value considered by strconv.ParseBool as true and any other value as false.
 func featureFlagsFromMap(featuresMap map[string]string, baseFeatureFlags model.FeatureFlags) model.FeatureFlags {
 	refStruct := reflect.ValueOf(&baseFeatureFlags).Elem()
 	for fieldName, fieldValue := range featuresMap {
@@ -83,13 +86,20 @@ func featureFlagsFromMap(featuresMap map[string]string, baseFeatureFlags model.F
 			continue
 		}
 
-		refField.Set(reflect.ValueOf(fieldValue))
+		switch refField.Type().Kind() {
+		case reflect.Bool:
+			parsedBoolValue, _ := strconv.ParseBool(fieldValue)
+			refField.Set(reflect.ValueOf(strings.ToLower(fieldValue) == "on" || parsedBoolValue))
+		default:
+			refField.Set(reflect.ValueOf(fieldValue))
+		}
+
 	}
 	return baseFeatureFlags
 }
 
 // featureFlagsToMap returns the feature flags as a map[string]string
-// Currently assumes that all feature flags are strings for now.
+// Supports boolean and string feature flags.
 func featureFlagsToMap(featureFlags *model.FeatureFlags) map[string]string {
 	refStructVal := reflect.ValueOf(*featureFlags)
 	refStructType := reflect.TypeOf(*featureFlags)
@@ -100,7 +110,12 @@ func featureFlagsToMap(featureFlags *model.FeatureFlags) map[string]string {
 		if !refFieldVal.IsValid() {
 			continue
 		}
-		ret[refFieldType.Name] = refFieldVal.String()
+		switch refFieldType.Type.Kind() {
+		case reflect.Bool:
+			ret[refFieldType.Name] = strconv.FormatBool(refFieldVal.Bool())
+		default:
+			ret[refFieldType.Name] = refFieldVal.String()
+		}
 	}
 
 	return ret
diff --git a/config/feature_flags_test.go b/config/feature_flags_test.go
index 3acf2372e9..8d5fe141b6 100644
--- a/config/feature_flags_test.go
+++ b/config/feature_flags_test.go
@@ -67,6 +67,41 @@ func TestFeatureFlagsFromMap(t *testing.T) {
 			Base:              model.FeatureFlags{},
 			ExpectedTestValue: "",
 		},
+		"bool on": {
+			FeatureMap:        map[string]string{"TestBoolFeature": "on"},
+			Base:              model.FeatureFlags{TestBoolFeature: true},
+			ExpectedTestValue: "",
+		},
+		"bool true": {
+			FeatureMap:        map[string]string{"TestBoolFeature": "true"},
+			Base:              model.FeatureFlags{TestBoolFeature: true},
+			ExpectedTestValue: "",
+		},
+		"bool True": {
+			FeatureMap:        map[string]string{"TestBoolFeature": "True"},
+			Base:              model.FeatureFlags{TestBoolFeature: true},
+			ExpectedTestValue: "",
+		},
+		"bool 1": {
+			FeatureMap:        map[string]string{"TestBoolFeature": "1"},
+			Base:              model.FeatureFlags{TestBoolFeature: true},
+			ExpectedTestValue: "",
+		},
+		"bool off": {
+			FeatureMap:        map[string]string{"TestBoolFeature": "off"},
+			Base:              model.FeatureFlags{},
+			ExpectedTestValue: "",
+		},
+		"bool false": {
+			FeatureMap:        map[string]string{"TestBoolFeature": "false"},
+			Base:              model.FeatureFlags{},
+			ExpectedTestValue: "",
+		},
+		"bool other value": {
+			FeatureMap:        map[string]string{"TestBoolFeature": "someotherbadvalue"},
+			Base:              model.FeatureFlags{},
+			ExpectedTestValue: "",
+		},
 	} {
 		t.Run(name, func(t *testing.T) {
 			require.Equal(t, tc.ExpectedTestValue, featureFlagsFromMap(tc.FeatureMap, tc.Base).TestFeature)
@@ -97,3 +132,23 @@ func TestFeatureFlagsToMap(t *testing.T) {
 		})
 	}
 }
+
+func TestFeatureFlagsToMapBool(t *testing.T) {
+	for name, tc := range map[string]struct {
+		Flags            model.FeatureFlags
+		TestFeatureValue string
+	}{
+		"false": {
+			TestFeatureValue: "false",
+			Flags:            model.FeatureFlags{},
+		},
+		"true": {
+			TestFeatureValue: "true",
+			Flags:            model.FeatureFlags{TestBoolFeature: true},
+		},
+	} {
+		t.Run(name, func(t *testing.T) {
+			require.Equal(t, tc.TestFeatureValue, featureFlagsToMap(&tc.Flags)["TestBoolFeature"])
+		})
+	}
+}
diff --git a/model/feature_flags.go b/model/feature_flags.go
index 316c7ffb9a..e260c877be 100644
--- a/model/feature_flags.go
+++ b/model/feature_flags.go
@@ -7,6 +7,9 @@ type FeatureFlags struct {
 	// Exists only for unit and manual testing.
 	// When set to a value, will be returned by the ping endpoint.
 	TestFeature string
+	// Exists only for testing bool functionality. Boolean feature flags interprate "on" or "true" as true and
+	// all other values as false.
+	TestBoolFeature bool
 
 	// Toggle on and off scheduled jobs for cloud user limit emails see MM-29999
 	CloudDelinquentEmailJobsEnabled bool
@@ -14,5 +17,6 @@ type FeatureFlags struct {
 
 func (f *FeatureFlags) SetDefaults() {
 	f.TestFeature = "off"
+	f.TestBoolFeature = false
 	f.CloudDelinquentEmailJobsEnabled = false
 }