diff --git a/app/common/src/main/java/stirling/software/common/service/TempFileCleanupService.java b/app/common/src/main/java/stirling/software/common/service/TempFileCleanupService.java
index 81b45aed09..438481c212 100644
--- a/app/common/src/main/java/stirling/software/common/service/TempFileCleanupService.java
+++ b/app/common/src/main/java/stirling/software/common/service/TempFileCleanupService.java
@@ -144,8 +144,10 @@ public class TempFileCleanupService {
         int directoriesDeletedCount = 0;
         for (Path directory : registry.getTempDirectories()) {
             try {
-                if (Files.exists(directory)) {
+                if (Files.exists(directory)
+                        && shouldDeleteRegisteredDirectory(directory, maxAgeMillis)) {
                     GeneralUtils.deleteDirectory(directory);
+                    registry.unregisterDirectory(directory);
                     directoriesDeletedCount++;
                     log.debug("Cleaned up temporary directory: {}", directory);
                 }
@@ -275,6 +277,21 @@ public class TempFileCleanupService {
         return totalDeletedCount.get();
     }
 
+    private boolean shouldDeleteRegisteredDirectory(Path directory, long maxAgeMillis) {
+        if (maxAgeMillis <= 0) {
+            return true;
+        }
+
+        try {
+            long currentTime = System.currentTimeMillis();
+            long lastModified = Files.getLastModifiedTime(directory).toMillis();
+            return (currentTime - lastModified) > maxAgeMillis;
+        } catch (IOException e) {
+            log.debug("Could not check directory age, skipping cleanup: {}", directory, e);
+            return false;
+        }
+    }
+
     /** Get the system temp directory path based on configuration or system property. */
     private Path getSystemTempPath() {
         String systemTempDir =
diff --git a/app/common/src/main/java/stirling/software/common/util/TempFileManager.java b/app/common/src/main/java/stirling/software/common/util/TempFileManager.java
index ff31975837..0d977e7d06 100644
--- a/app/common/src/main/java/stirling/software/common/util/TempFileManager.java
+++ b/app/common/src/main/java/stirling/software/common/util/TempFileManager.java
@@ -155,6 +155,7 @@ public class TempFileManager {
         if (directory != null && Files.isDirectory(directory)) {
             try {
                 GeneralUtils.deleteDirectory(directory);
+                registry.unregisterDirectory(directory);
                 log.debug("Deleted temp directory: {}", directory.toString());
             } catch (IOException e) {
                 log.warn("Failed to delete temp directory: {}", directory.toString(), e);
diff --git a/app/common/src/main/java/stirling/software/common/util/TempFileRegistry.java b/app/common/src/main/java/stirling/software/common/util/TempFileRegistry.java
index ab1304f5e4..84a3c12272 100644
--- a/app/common/src/main/java/stirling/software/common/util/TempFileRegistry.java
+++ b/app/common/src/main/java/stirling/software/common/util/TempFileRegistry.java
@@ -85,6 +85,18 @@ public class TempFileRegistry {
         return directory;
     }
 
+    /**
+     * Unregister a temporary directory from the registry.
+     *
+     * @param directory The directory to unregister
+     */
+    public void unregisterDirectory(Path directory) {
+        if (directory != null) {
+            tempDirectories.remove(directory);
+            log.debug("Unregistered temp directory: {}", directory.toString());
+        }
+    }
+
     /**
      * Register a third-party temporary file that requires special handling.
      *
diff --git a/app/common/src/test/java/stirling/software/common/service/TempFileCleanupServiceMoreTest.java b/app/common/src/test/java/stirling/software/common/service/TempFileCleanupServiceMoreTest.java
index 802dc2eace..cfbe950574 100644
--- a/app/common/src/test/java/stirling/software/common/service/TempFileCleanupServiceMoreTest.java
+++ b/app/common/src/test/java/stirling/software/common/service/TempFileCleanupServiceMoreTest.java
@@ -176,11 +176,13 @@ class TempFileCleanupServiceMoreTest {
     class ScheduledCleanup {
 
         @Test
-        @DisplayName("deletes registered temp directories and reports counts")
+        @DisplayName("deletes stale registered temp directories and reports counts")
         void deletesRegisteredDirectories() throws IOException {
             when(tempFileManager.cleanupOldTempFiles(anyLong())).thenReturn(2);
             Path regDir = Files.createDirectories(tempDir.resolve("registeredDir"));
             Files.createFile(regDir.resolve("inside.txt"));
+            Files.setLastModifiedTime(
+                    regDir, FileTime.fromMillis(System.currentTimeMillis() - 2L * 60 * 60 * 1000));
             Set<Path> dirs = new HashSet<>();
             dirs.add(regDir);
             when(registry.getTempDirectories()).thenReturn(dirs);
@@ -193,6 +195,22 @@ class TempFileCleanupServiceMoreTest {
             verify(tempFileManager).cleanupOldTempFiles(anyLong());
         }
 
+        @Test
+        @DisplayName("keeps a fresh registered temp directory")
+        void keepsFreshRegisteredDirectory() throws IOException {
+            when(tempFileManager.cleanupOldTempFiles(anyLong())).thenReturn(0);
+            Path regDir = Files.createDirectories(tempDir.resolve("freshRegisteredDir"));
+            Files.createFile(regDir.resolve("inside.txt"));
+            Set<Path> dirs = new HashSet<>();
+            dirs.add(regDir);
+            when(registry.getTempDirectories()).thenReturn(dirs);
+            lenient().when(registry.contains(any(File.class))).thenReturn(false);
+
+            withIsolatedUserHome(cleanupService::scheduledCleanup);
+
+            assertThat(Files.exists(regDir)).isTrue();
+        }
+
         @Test
         @DisplayName("skips a registered directory that no longer exists")
         void skipsMissingRegisteredDirectory() {