diff --git a/server/src/internalClusterTest/java/org/elasticsearch/readiness/ReadinessClusterIT.java b/server/src/internalClusterTest/java/org/elasticsearch/readiness/ReadinessClusterIT.java
index 2ecdd06f379d2..1f8d55516d508 100644
--- a/server/src/internalClusterTest/java/org/elasticsearch/readiness/ReadinessClusterIT.java
+++ b/server/src/internalClusterTest/java/org/elasticsearch/readiness/ReadinessClusterIT.java
@@ -251,7 +251,6 @@ private void writeFileSettings(String json) throws Exception {
         logger.info("--> New file settings: [{}]", Strings.format(json, version));
     }
 
-    @AwaitsFix(bugUrl = "https://github.com/elastic/elasticsearch/issues/107744")
     public void testNotReadyOnBadFileSettings() throws Exception {
         internalCluster().setBootstrapMasterNodeIndex(0);
         logger.info("--> start data node / non master node");
diff --git a/server/src/main/java/org/elasticsearch/cluster/metadata/ReservedStateMetadata.java b/server/src/main/java/org/elasticsearch/cluster/metadata/ReservedStateMetadata.java
index dd5ca03cf759a..ec8200bf2d701 100644
--- a/server/src/main/java/org/elasticsearch/cluster/metadata/ReservedStateMetadata.java
+++ b/server/src/main/java/org/elasticsearch/cluster/metadata/ReservedStateMetadata.java
@@ -46,6 +46,8 @@ public record ReservedStateMetadata(
     ReservedStateErrorMetadata errorMetadata
 ) implements SimpleDiffable<ReservedStateMetadata>, ToXContentFragment {
 
+    public static final Long NO_VERSION = Long.MIN_VALUE; // use min long as sentinel for uninitialized version
+
     private static final ParseField VERSION = new ParseField("version");
     private static final ParseField HANDLERS = new ParseField("handlers");
     private static final ParseField ERRORS_METADATA = new ParseField("errors");
@@ -209,7 +211,7 @@ public static class Builder {
          */
         public Builder(String namespace) {
             this.namespace = namespace;
-            this.version = -1L;
+            this.version = NO_VERSION;
             this.handlers = new HashMap<>();
             this.errorMetadata = null;
         }
diff --git a/server/src/main/java/org/elasticsearch/readiness/ReadinessService.java b/server/src/main/java/org/elasticsearch/readiness/ReadinessService.java
index 1cac133106403..61425250c19b4 100644
--- a/server/src/main/java/org/elasticsearch/readiness/ReadinessService.java
+++ b/server/src/main/java/org/elasticsearch/readiness/ReadinessService.java
@@ -254,7 +254,7 @@ public void clusterChanged(ClusterChangedEvent event) {
     // protected to allow mock service to override
     protected boolean areFileSettingsApplied(ClusterState clusterState) {
         ReservedStateMetadata fileSettingsMetadata = clusterState.metadata().reservedStateMetadata().get(FileSettingsService.NAMESPACE);
-        return fileSettingsMetadata != null;
+        return fileSettingsMetadata != null && fileSettingsMetadata.version().equals(ReservedStateMetadata.NO_VERSION) == false;
     }
 
     private void setReady(boolean ready) {
diff --git a/server/src/test/java/org/elasticsearch/cluster/metadata/ReservedStateMetadataTests.java b/server/src/test/java/org/elasticsearch/cluster/metadata/ReservedStateMetadataTests.java
index 46be49ad7111f..5086813cc5c13 100644
--- a/server/src/test/java/org/elasticsearch/cluster/metadata/ReservedStateMetadataTests.java
+++ b/server/src/test/java/org/elasticsearch/cluster/metadata/ReservedStateMetadataTests.java
@@ -20,6 +20,7 @@
 import java.util.Collections;
 import java.util.List;
 
+import static org.elasticsearch.cluster.metadata.ReservedStateMetadata.NO_VERSION;
 import static org.hamcrest.Matchers.equalTo;
 import static org.hamcrest.Matchers.not;
 
@@ -78,7 +79,7 @@ public void testXContent() throws IOException {
 
     public void testReservedStateVersionWithError() {
         final ReservedStateMetadata meta = createRandom(false, true);
-        assertEquals(-1L, meta.version().longValue());
+        assertEquals(NO_VERSION.longValue(), meta.version().longValue());
     }
 
     private static ReservedStateMetadata createRandom(boolean addHandlers, boolean addErrors) {
diff --git a/server/src/test/java/org/elasticsearch/cluster/metadata/ToAndFromJsonMetadataTests.java b/server/src/test/java/org/elasticsearch/cluster/metadata/ToAndFromJsonMetadataTests.java
index aa9d0b9368fa6..3a522f3f5c06c 100644
--- a/server/src/test/java/org/elasticsearch/cluster/metadata/ToAndFromJsonMetadataTests.java
+++ b/server/src/test/java/org/elasticsearch/cluster/metadata/ToAndFromJsonMetadataTests.java
@@ -776,7 +776,7 @@ public void testToXContentAPIReservedMetadata() throws IOException {
                 },
                 "reserved_state" : {
                   "namespace_one" : {
-                    "version" : -1,
+                    "version" : -9223372036854775808,
                     "handlers" : {
                       "one" : {
                         "keys" : [
@@ -801,7 +801,7 @@ public void testToXContentAPIReservedMetadata() throws IOException {
                     }
                   },
                   "namespace_two" : {
-                    "version" : -1,
+                    "version" : -9223372036854775808,
                     "handlers" : {
                       "three" : {
                         "keys" : [