diff --git a/src/gui/src/MainWindow.cpp b/src/gui/src/MainWindow.cpp
index 87f31eb2..7d4a9a5e 100644
--- a/src/gui/src/MainWindow.cpp
+++ b/src/gui/src/MainWindow.cpp
@@ -444,6 +444,11 @@ void MainWindow::checkFingerprint(const QString& line)
 
     auto db_path = barrier::DataDirectories::trusted_servers_ssl_fingerprints_path();
 
+    auto db_dir = db_path.parent_path();
+    if (!barrier::fs::exists(db_dir)) {
+        barrier::fs::create_directories(db_dir);
+    }
+
     // We compare only SHA256 fingerprints, but show both SHA1 and SHA256 so that the users can
     // still verify fingerprints on old Barrier servers. This way the only time when we are exposed
     // to SHA1 vulnerabilities is when the user is reconnecting again.
diff --git a/src/gui/src/SslCertificate.cpp b/src/gui/src/SslCertificate.cpp
index 26f3b3ee..65ac08a6 100644
--- a/src/gui/src/SslCertificate.cpp
+++ b/src/gui/src/SslCertificate.cpp
@@ -65,6 +65,11 @@ void SslCertificate::generate_fingerprint(const barrier::fs::path& cert_path)
 {
     try {
         auto local_path = barrier::DataDirectories::local_ssl_fingerprints_path();
+        auto local_dir = local_path.parent_path();
+        if (!barrier::fs::exists(local_dir)) {
+            barrier::fs::create_directories(local_dir);
+        }
+
         barrier::FingerprintDatabase db;
         db.add_trusted(barrier::get_pem_file_cert_fingerprint(cert_path.u8string(),
                                                               barrier::FingerprintType::SHA1));