diff --git a/CHANGES.txt b/CHANGES.txt
index aa1e60427a..0e6554c1ab 100644
--- a/CHANGES.txt
+++ b/CHANGES.txt
@@ -1,4 +1,5 @@
 3.0.29
+ * Fix the ordering of sstables when running sstableupgrade tool (CASSANDRA-18143)
  * Fix default file system error handler for disk_failure_policy die (CASSANDRA-18294)
  * Introduce check for names of test classes (CASSANDRA-17964)
  * Suppress CVE-2022-41915 (CASSANDRA-18147)
diff --git a/src/java/org/apache/cassandra/db/Directories.java b/src/java/org/apache/cassandra/db/Directories.java
index d169428c1e..7ee7579f0b 100644
--- a/src/java/org/apache/cassandra/db/Directories.java
+++ b/src/java/org/apache/cassandra/db/Directories.java
@@ -671,6 +671,18 @@ public class Directories
             return ImmutableMap.copyOf(components);
         }
 
+        /**
+         * Returns a sorted version of the {@code list} method.
+         * Descriptors are sorted by generation.
+         * @return a List of descriptors to their components.
+         */
+        public List<Map.Entry<Descriptor, Set<Component>>> sortedList()
+        {
+            List<Map.Entry<Descriptor, Set<Component>>> sortedEntries = new ArrayList<>(list().entrySet());
+            sortedEntries.sort(Comparator.comparingInt(e -> e.getKey().generation));
+            return sortedEntries;
+        }
+
         public List<File> listFiles()
         {
             filter();
diff --git a/src/java/org/apache/cassandra/tools/StandaloneUpgrader.java b/src/java/org/apache/cassandra/tools/StandaloneUpgrader.java
index f2a922b398..50f7331674 100644
--- a/src/java/org/apache/cassandra/tools/StandaloneUpgrader.java
+++ b/src/java/org/apache/cassandra/tools/StandaloneUpgrader.java
@@ -72,8 +72,8 @@ public class StandaloneUpgrader
 
             Collection<SSTableReader> readers = new ArrayList<>();
 
-            // Upgrade sstables
-            for (Map.Entry<Descriptor, Set<Component>> entry : lister.list().entrySet())
+            // Upgrade sstables in id order
+            for (Map.Entry<Descriptor, Set<Component>> entry : lister.sortedList())
             {
                 Set<Component> components = entry.getValue();
                 if (!components.contains(Component.DATA) || !components.contains(Component.PRIMARY_INDEX))