diff --git a/src/config.c b/src/config.c
index 0d435fecb..f7252ca6e 100644
--- a/src/config.c
+++ b/src/config.c
@@ -311,18 +311,21 @@ int configEnumGetValue(configEnum *ce, sds *argv, int argc, int bitflags) {
 /* Get enum name/s from value. If no matches are found "unknown" is returned. */
 static sds configEnumGetName(configEnum *ce, int values, int bitflags) {
     sds names = NULL;
-    int matches = 0;
+    int unmatched = values;
     for( ; ce->name != NULL; ce++) {
         if (values == ce->val) { /* Short path for perfect match */
             sdsfree(names);
             return sdsnew(ce->name);
         }
-        if (bitflags && (values & ce->val)) {
+
+        /* Note: for bitflags, we want them sorted from high to low, so that if there are several / partially
+         * overlapping entries, we'll prefer the ones matching more bits. */
+        if (bitflags && ce->val && ce->val == (unmatched & ce->val)) {
             names = names ? sdscatfmt(names, " %s", ce->name) : sdsnew(ce->name);
-            matches |= ce->val;
+            unmatched &= ~ce->val;
         }
     }
-    if (!names || values != matches) {
+    if (!names || unmatched) {
         sdsfree(names);
         return sdsnew("unknown");
     }
diff --git a/src/module.c b/src/module.c
index 4bdaecb8a..3ef8e6f0a 100644
--- a/src/module.c
+++ b/src/module.c
@@ -11679,7 +11679,11 @@ int RM_RegisterBoolConfig(RedisModuleCtx *ctx, const char *name, int default_val
  *      }
  *      ...
  *      RedisModule_RegisterEnumConfig(ctx, "enum", 0, REDISMODULE_CONFIG_DEFAULT, enum_vals, int_vals, 3, getEnumConfigCommand, setEnumConfigCommand, NULL, NULL);
- * 
+ *
+ * Note that you can use REDISMODULE_CONFIG_BITFLAGS so that multiple enum string
+ * can be combined into one integer as bit flags, in which case you may want to
+ * sort your enums so that the preferred combinations are present first.
+ *
  * See RedisModule_RegisterStringConfig for detailed general information about configs. */
 int RM_RegisterEnumConfig(RedisModuleCtx *ctx, const char *name, int default_val, unsigned int flags, const char **enum_values, const int *int_values, int num_enum_vals, RedisModuleConfigGetEnumFunc getfn, RedisModuleConfigSetEnumFunc setfn, RedisModuleConfigApplyFunc applyfn, void *privdata) {
     RedisModule *module = ctx->module;
diff --git a/tests/modules/moduleconfigs.c b/tests/modules/moduleconfigs.c
index 0a6380461..b48133372 100644
--- a/tests/modules/moduleconfigs.c
+++ b/tests/modules/moduleconfigs.c
@@ -121,13 +121,13 @@ int RedisModule_OnLoad(RedisModuleCtx *ctx, RedisModuleString **argv, int argc)
     }
 
     /* On the stack to make sure we're copying them. */
-    const char *enum_vals[] = {"none", "one", "two", "three"};
-    const int int_vals[] = {0, 1, 2, 4};
+    const char *enum_vals[] = {"none", "five", "one", "two", "four"};
+    const int int_vals[] = {0, 5, 1, 2, 4};
 
-    if (RedisModule_RegisterEnumConfig(ctx, "enum", 1, REDISMODULE_CONFIG_DEFAULT, enum_vals, int_vals, 4, getEnumConfigCommand, setEnumConfigCommand, NULL, NULL) == REDISMODULE_ERR) {
+    if (RedisModule_RegisterEnumConfig(ctx, "enum", 1, REDISMODULE_CONFIG_DEFAULT, enum_vals, int_vals, 5, getEnumConfigCommand, setEnumConfigCommand, NULL, NULL) == REDISMODULE_ERR) {
         return REDISMODULE_ERR;
     }
-    if (RedisModule_RegisterEnumConfig(ctx, "flags", 3, REDISMODULE_CONFIG_DEFAULT | REDISMODULE_CONFIG_BITFLAGS, enum_vals, int_vals, 4, getFlagsConfigCommand, setFlagsConfigCommand, NULL, NULL) == REDISMODULE_ERR) {
+    if (RedisModule_RegisterEnumConfig(ctx, "flags", 3, REDISMODULE_CONFIG_DEFAULT | REDISMODULE_CONFIG_BITFLAGS, enum_vals, int_vals, 5, getFlagsConfigCommand, setFlagsConfigCommand, NULL, NULL) == REDISMODULE_ERR) {
         return REDISMODULE_ERR;
     }
     /* Memory config here. */
diff --git a/tests/unit/moduleapi/moduleconfigs.tcl b/tests/unit/moduleapi/moduleconfigs.tcl
index f731d1bd9..8ebce3514 100644
--- a/tests/unit/moduleapi/moduleconfigs.tcl
+++ b/tests/unit/moduleapi/moduleconfigs.tcl
@@ -32,12 +32,27 @@ start_server {tags {"modules"}} {
         assert_equal [r config get moduleconfigs.enum] "moduleconfigs.enum two"
         r config set moduleconfigs.flags two
         assert_equal [r config get moduleconfigs.flags] "moduleconfigs.flags two"
-        r config set moduleconfigs.flags "two three"
-        assert_equal [r config get moduleconfigs.flags] "moduleconfigs.flags {two three}"
         r config set moduleconfigs.numeric -2
         assert_equal [r config get moduleconfigs.numeric] "moduleconfigs.numeric -2"
     }
 
+    test {Config set commands enum flags} {
+        r config set moduleconfigs.flags "none"
+        assert_equal [r config get moduleconfigs.flags] "moduleconfigs.flags none"
+
+        r config set moduleconfigs.flags "two four"
+        assert_equal [r config get moduleconfigs.flags] "moduleconfigs.flags {two four}"
+
+        r config set moduleconfigs.flags "five"
+        assert_equal [r config get moduleconfigs.flags] "moduleconfigs.flags five"
+
+        r config set moduleconfigs.flags "one four"
+        assert_equal [r config get moduleconfigs.flags] "moduleconfigs.flags five"
+
+        r config set moduleconfigs.flags "one two four"
+        assert_equal [r config get moduleconfigs.flags] "moduleconfigs.flags {five two}"
+    }
+
     test {Immutable flag works properly and rejected strings dont leak} {
         # Configs flagged immutable should not allow sets
         catch {[r config set moduleconfigs.immutable_bool yes]} e
@@ -58,7 +73,7 @@ start_server {tags {"modules"}} {
 
     test {Enums only able to be set to passed in values} {
         # Module authors specify what values are valid for enums, check that only those values are ok on a set
-        catch {[r config set moduleconfigs.enum four]} e
+        catch {[r config set moduleconfigs.enum asdf]} e
         assert_match {*must be one of the following*} $e
     }
 
@@ -147,7 +162,7 @@ start_server {tags {"modules"}} {
         r config set moduleconfigs.mutable_bool yes
         r config set moduleconfigs.memory_numeric 750
         r config set moduleconfigs.enum two
-        r config set moduleconfigs.flags "two three"
+        r config set moduleconfigs.flags "four two"
         r config rewrite
         restart_server 0 true false
         # Ensure configs we rewrote are present and that the conf file is readable
@@ -155,7 +170,7 @@ start_server {tags {"modules"}} {
         assert_equal [r config get moduleconfigs.memory_numeric] "moduleconfigs.memory_numeric 750"
         assert_equal [r config get moduleconfigs.string] "moduleconfigs.string {super \0secret password}"
         assert_equal [r config get moduleconfigs.enum] "moduleconfigs.enum two"
-        assert_equal [r config get moduleconfigs.flags] "moduleconfigs.flags {two three}"
+        assert_equal [r config get moduleconfigs.flags] "moduleconfigs.flags {two four}"
         assert_equal [r config get moduleconfigs.numeric] "moduleconfigs.numeric -1"
         r module unload moduleconfigs
     }
@@ -230,12 +245,12 @@ start_server {tags {"modules"}} {
         set stdout [dict get $noload stdout]
         assert_equal [count_message_lines $stdout "Module Configurations were not set, likely a missing LoadConfigs call. Unloading the module."] 1
 
-        start_server [list overrides [list loadmodule "$testmodule" moduleconfigs.string "bootedup" moduleconfigs.enum two moduleconfigs.flags "two three"]] {
+        start_server [list overrides [list loadmodule "$testmodule" moduleconfigs.string "bootedup" moduleconfigs.enum two moduleconfigs.flags "two four"]] {
             assert_equal [r config get moduleconfigs.string] "moduleconfigs.string bootedup"
             assert_equal [r config get moduleconfigs.mutable_bool] "moduleconfigs.mutable_bool yes"
             assert_equal [r config get moduleconfigs.immutable_bool] "moduleconfigs.immutable_bool no"
             assert_equal [r config get moduleconfigs.enum] "moduleconfigs.enum two"
-            assert_equal [r config get moduleconfigs.flags] "moduleconfigs.flags {two three}"
+            assert_equal [r config get moduleconfigs.flags] "moduleconfigs.flags {two four}"
             assert_equal [r config get moduleconfigs.numeric] "moduleconfigs.numeric -1"
             assert_equal [r config get moduleconfigs.memory_numeric] "moduleconfigs.memory_numeric 1024"
         }