diff --git a/README.md b/README.md
index d55e9bb..d5bd35f 100644
--- a/README.md
+++ b/README.md
@@ -21,7 +21,7 @@ Write access is controlled by tokens.
    - `curl http://localhost:8123/meta/squashkiwi:latest`
 - a simple welcome page is served at `/index.html` for those browsing to the site.
 - to upload a file (via http put)
-   - `curl -T object_file http://localhost:8123/WRITE_TOKEN/LABEL:TAG`
+   - `curl -T object_file http://localhost:8123/WRITE_TOKEN/LABEL:TAG?filename="FILENAME"`
    - the object_file is uploaded, hashed, added to the registry (if that hash doesn't already exist), and {label:tag,hash} is added to the directory index.
 - the server is configured via a configuration file which allows setting:
    - the list of write access tokens
diff --git a/src/compress.cpp b/src/compress.cpp
index e4800a6..1647199 100644
--- a/src/compress.cpp
+++ b/src/compress.cpp
@@ -22,9 +22,10 @@ uint64_t get_hash_from_tgz(const std::string &file_path)
     std::ifstream file(file_path, std::ios::binary);
     if (!file) return 0;
 
-    char buffer[2];
-    file.read(buffer, 2);
-    if (buffer[0] != 0x1F || buffer[1] != 0x8B) return 0;
+    int result = system("gunzip -t file.gz");
+    if (result != 0) { // not a gzip file.
+        return 0;
+    }
 
     // gunzip the file to a new temporary directory
     TempDirectory temp_dir_manager("tgz_unpack_"); // Creates dir and schedules cleanup
@@ -32,9 +33,8 @@ uint64_t get_hash_from_tgz(const std::string &file_path)
 
     // unpack the file on disk
     std::string command = "tar -zxzf " + file_path + " -C " + temp_dir;
-    int result = system(command.c_str()); // Basic tar extraction - requires 'tar' command
+    result = system(command.c_str()); // Basic tar extraction - requires 'tar' command
     if (result != 0) {
-        std::cerr << "Error unpacking tgz file: " << file_path << std::endl;
         return 0;
     }
 
diff --git a/src/database.cpp b/src/database.cpp
index 647a22d..bae4292 100644
--- a/src/database.cpp
+++ b/src/database.cpp
@@ -228,4 +228,22 @@ bool Database::list(std::vector<dbEntry>& entries) {
     return true;
 }
 
+bool Database::update_or_insert(const dbEntry& entry) {
+    std::string sql = "INSERT OR REPLACE INTO objects (label_tag, hash, metadata) VALUES (?, ?, ?);";
+    sqlite3_stmt* stmt;
+    
+    if (sqlite3_prepare_v2(db_, sql.c_str(), -1, &stmt, nullptr) != SQLITE_OK) {
+        return false;
+    }
+
+    sqlite3_bind_text(stmt, 1, entry.label_tag.c_str(), -1, SQLITE_STATIC);
+    sqlite3_bind_text(stmt, 2, entry.hash.c_str(), -1, SQLITE_STATIC);
+    std::string metadata_str = entry.metadata.dump();
+    sqlite3_bind_text(stmt, 3, metadata_str.c_str(), -1, SQLITE_STATIC);
+
+    bool success = sqlite3_step(stmt) == SQLITE_DONE;
+    sqlite3_finalize(stmt);
+    return success;
+}
+
 } // namespace simple_object_storage
diff --git a/src/database.hpp b/src/database.hpp
index ae2f000..a3f927c 100644
--- a/src/database.hpp
+++ b/src/database.hpp
@@ -25,7 +25,8 @@ class Database {
         bool remove(const std::string& label_tag);
         bool get(const std::string& label_tag, dbEntry& entry);
         bool update(const std::string& label_tag, const dbEntry& entry);
-        bool list(std::vector<dbEntry>& entries);        
+        bool list(std::vector<dbEntry>& entries);
+        bool update_or_insert(const dbEntry& entry);
     private:
         std::filesystem::path path_;
         sqlite3* db_;
diff --git a/src/server.cpp b/src/server.cpp
index 031ec39..3b962a3 100644
--- a/src/server.cpp
+++ b/src/server.cpp
@@ -13,6 +13,7 @@
 #include "server.hpp"
 #include "hash.hpp"
 #include "compress.hpp"
+#include "string_utils.hpp" // Include the new utility header
 
 
 namespace simple_object_storage {
@@ -265,7 +266,21 @@ void Server::handle_put_object(const httplib::Request& req, httplib::Response& r
         return;
     }
 
-    nlohmann::json metadata = get_metadata(temp_path.string());
+    nlohmann::json metadata; 
+
+    // Check for filename query parameter
+    std::string filename = "";
+    if (req.has_param("filename")) {
+        filename = req.get_param_value("filename");
+        metadata["original_filename"] = filename;
+    }
+
+    // Check if filename ends with ".tgz" using the utility function
+    if (utils::ends_with(filename, ".tgz")) {
+        metadata["tgz_content_hash"] = get_hash_from_tgz(temp_path.string());
+    }
+
+    add_file_metadata(temp_path.string(), metadata);
 
     // Move file to final location
     std::string hash_str = std::to_string(hash);
@@ -286,9 +301,9 @@ void Server::handle_put_object(const httplib::Request& req, httplib::Response& r
     dbEntry entry;
     entry.label_tag = label_tag;
     entry.hash = hash_str;
-    entry.metadata = metadata; // Empty metadata for now
+    entry.metadata = metadata; // Store the potentially updated metadata
 
-    if (!db_->insert(entry)) {
+    if (!db_->update_or_insert(entry)) {
         res.status = 500;
         res.set_content("Failed to update database index", "text/plain");
         // Attempt to clean up the moved file if index fails
@@ -330,10 +345,8 @@ std::pair<std::string, std::string> Server::parse_label_tag(const std::string& l
     return {label_tag.substr(0, colon_pos), label_tag.substr(colon_pos + 1)};
 }
 
-nlohmann::json Server::get_metadata(const std::string &file_path) const
+void Server::add_file_metadata(const std::string &file_path, nlohmann::json &metadata) const
 {
-    nlohmann::json metadata;
-
     // get the file size
     metadata["file_size"] = std::filesystem::file_size(file_path);
 
@@ -344,10 +357,6 @@ nlohmann::json Server::get_metadata(const std::string &file_path) const
         + std::chrono::system_clock::now()
     );
     metadata["file_modification_time"] = std::chrono::system_clock::to_time_t(sctp);
-
-    metadata["tgz_content_hash"] = get_hash_from_tgz(file_path);
-
-    return metadata;
 }
 
 } // namespace simple_object_storage 
\ No newline at end of file
diff --git a/src/server.hpp b/src/server.hpp
index e68b0fe..a3c2c85 100644
--- a/src/server.hpp
+++ b/src/server.hpp
@@ -30,7 +30,7 @@ private:
     void handle_get_metadata(const httplib::Request& req, httplib::Response& res);
     bool validate_write_token(const std::string& token) const;
     std::pair<std::string, std::string> parse_label_tag(const std::string& label_tag) const;
-    nlohmann::json get_metadata(const std::string& file_path) const;
+    void add_file_metadata(const std::string &file_path, nlohmann::json &metadata) const;
 
     bool init_db();
 
diff --git a/src/string_utils.cpp b/src/string_utils.cpp
new file mode 100644
index 0000000..ae0e13e
--- /dev/null
+++ b/src/string_utils.cpp
@@ -0,0 +1,15 @@
+#include "string_utils.hpp"
+
+namespace simple_object_storage {
+namespace utils {
+
+bool ends_with(const std::string& value, const std::string& suffix) {
+    if (suffix.length() > value.length()) {
+        return false;
+    }
+    // Use rfind to check if the suffix matches the end of the value
+    return value.rfind(suffix) == value.length() - suffix.length();
+}
+
+} // namespace utils
+} // namespace simple_object_storage 
\ No newline at end of file
diff --git a/src/string_utils.hpp b/src/string_utils.hpp
new file mode 100644
index 0000000..517e0f5
--- /dev/null
+++ b/src/string_utils.hpp
@@ -0,0 +1,21 @@
+#ifndef STRING_UTILS_HPP
+#define STRING_UTILS_HPP
+
+#include <string>
+
+namespace simple_object_storage {
+namespace utils {
+
+/**
+ * @brief Checks if a string ends with a specified suffix.
+ * 
+ * @param value The string to check.
+ * @param suffix The suffix to look for.
+ * @return true if the string ends with the suffix, false otherwise.
+ */
+bool ends_with(const std::string& value, const std::string& suffix);
+
+} // namespace utils
+} // namespace simple_object_storage
+
+#endif // STRING_UTILS_HPP 
\ No newline at end of file