diff --git a/Core/src/org/sleuthkit/autopsy/modules/hashdatabase/HashDbCreateDatabaseDialog.java b/Core/src/org/sleuthkit/autopsy/modules/hashdatabase/HashDbCreateDatabaseDialog.java
index dd51fc15ba7cde1deac7bf5e8f5fc0dbf1ac159a..b132a8541e0415612d7192160f109202786961a8 100644
--- a/Core/src/org/sleuthkit/autopsy/modules/hashdatabase/HashDbCreateDatabaseDialog.java
+++ b/Core/src/org/sleuthkit/autopsy/modules/hashdatabase/HashDbCreateDatabaseDialog.java
@@ -432,7 +432,7 @@ private void saveAsButtonActionPerformed(java.awt.event.ActionEvent evt) {//GEN-
             File hashDbFolder = new File(path.toString());
             // create the folder if it doesn't exist
             if (!hashDbFolder.exists()) {
-                hashDbFolder.mkdir();
+                hashDbFolder.mkdirs();
             }
             if (!hashSetNameTextField.getText().isEmpty()) {
                 path.append(File.separator).append(hashSetNameTextField.getText());
diff --git a/Core/src/org/sleuthkit/autopsy/modules/hashdatabase/HashDbImportDatabaseDialog.java b/Core/src/org/sleuthkit/autopsy/modules/hashdatabase/HashDbImportDatabaseDialog.java
index b6838f3adf7eca8680e448d8d59b3a75a5e5e8a9..c9b4602dcf7ec27cb896e8c93bb1bc3c5d59a6e3 100644
--- a/Core/src/org/sleuthkit/autopsy/modules/hashdatabase/HashDbImportDatabaseDialog.java
+++ b/Core/src/org/sleuthkit/autopsy/modules/hashdatabase/HashDbImportDatabaseDialog.java
@@ -430,7 +430,7 @@ private void openButtonActionPerformed(java.awt.event.ActionEvent evt) {//GEN-FI
         File hashDbFolder = new File(lastBaseDirectory);
         // create the folder if it doesn't exist
         if (!hashDbFolder.exists()) {
-            hashDbFolder.mkdir();
+            hashDbFolder.mkdirs();
         }
         fileChooser.setCurrentDirectory(hashDbFolder);
         if (fileChooser.showOpenDialog(this) == JFileChooser.APPROVE_OPTION) {
@@ -534,7 +534,9 @@ private void okButtonActionPerformed(java.awt.event.ActionEvent evt) {//GEN-FIRS
             // copy the hash database to user configuration directory and use that path instead (JIRA-4177)
             String locationInUserConfigDir = Paths.get(HashLookupSettings.getBaseHashsetConfigPath(), HashDbCreateDatabaseDialog.HASH_DATABASE_DIR_NAME, hashSetNameTextField.getText(), file.getName()).toString();
             try {
-                FileUtils.copyFile(file, new File(locationInUserConfigDir));
+                File newFileLoc = new File(locationInUserConfigDir);
+                newFileLoc.getParentFile().mkdirs();
+                FileUtils.copyFile(file, newFileLoc);
                 // update the hash database location
                 selectedFilePath = locationInUserConfigDir;
             } catch (IOException ex) {
diff --git a/Core/src/org/sleuthkit/autopsy/modules/interestingitems/FileSetsDefinitions.java b/Core/src/org/sleuthkit/autopsy/modules/interestingitems/FileSetsDefinitions.java
index bca8a2d750cfe756cbe361487203b21199775c44..e2f353fee1e0f93245247a4718eddeff71792653 100644
--- a/Core/src/org/sleuthkit/autopsy/modules/interestingitems/FileSetsDefinitions.java
+++ b/Core/src/org/sleuthkit/autopsy/modules/interestingitems/FileSetsDefinitions.java
@@ -61,7 +61,7 @@ Map<String, FilesSet> getFilesSets() {
      */
     static boolean writeDefinitionsFile(String basePath, String fileName, Map<String, FilesSet> interestingFilesSets) throws FilesSetsManager.FilesSetsManagerException {
         File outputPath = Paths.get(basePath, fileName).toFile();
-        outputPath.mkdirs();
+        outputPath.getParentFile().mkdirs();
         try (final NbObjectOutputStream out = new NbObjectOutputStream(new FileOutputStream(outputPath))) {
             out.writeObject(new FileSetsDefinitions(interestingFilesSets));
         } catch (IOException ex) {
diff --git a/Core/src/org/sleuthkit/autopsy/modules/interestingitems/InterestingItemsFilesSetSettings.java b/Core/src/org/sleuthkit/autopsy/modules/interestingitems/InterestingItemsFilesSetSettings.java
index 376f1d5693b61dec4daf9f09d6817634d7a1c5af..e1655001321d413875aeb49c101ef64c71497eea 100644
--- a/Core/src/org/sleuthkit/autopsy/modules/interestingitems/InterestingItemsFilesSetSettings.java
+++ b/Core/src/org/sleuthkit/autopsy/modules/interestingitems/InterestingItemsFilesSetSettings.java
@@ -608,7 +608,7 @@ static Map<String, FilesSet> readDefinitionsXML(Document doc, String resourceNam
      */
     static boolean writeDefinitionsFile(String basePath, String fileName, Map<String, FilesSet> interestingFilesSets) throws FilesSetsManager.FilesSetsManagerException {
         File outputFile = Paths.get(basePath, fileName).toFile();
-        outputFile.mkdirs();
+        outputFile.getParentFile().mkdirs();
         try (final NbObjectOutputStream out = new NbObjectOutputStream(new FileOutputStream(outputFile))) {
             out.writeObject(new InterestingItemsFilesSetSettings(interestingFilesSets));
         } catch (IOException ex) {