diff --git a/nix/checks/default.nix b/nix/checks/default.nix
index dd9c5f9..f03c008 100644
--- a/nix/checks/default.nix
+++ b/nix/checks/default.nix
@@ -27,4 +27,9 @@
     inherit craneLib src;
     lib = pkgs.lib;
   };
+
+  # End-to-end tests
+  e2e-tests = import ./e2e-test.nix {
+    inherit pkgs vault-hier src;
+  };
 }
diff --git a/nix/checks/e2e-test.nix b/nix/checks/e2e-test.nix
new file mode 100644
index 0000000..a6ebc1e
--- /dev/null
+++ b/nix/checks/e2e-test.nix
@@ -0,0 +1,188 @@
+{ pkgs, vault-hier, src }:
+
+let
+  # Create a test script to run the end-to-end tests
+  e2eTestScript = pkgs.writeShellScriptBin "run-e2e-tests" ''
+    #!/usr/bin/env bash
+    set -euo pipefail
+
+    # Create temporary directories for test data, vault, and pid files
+    TEST_DIR=$(mktemp -d)
+    VAULT_TEST_DIR=$(mktemp -d)
+    VAULT_PID_FILE="$TEST_DIR/vault.pid"
+
+    # Set Vault address
+    export VAULT_ADDR="http://127.0.0.1:8200"
+
+    # Use a fixed port for the API to make debugging easier
+    API_PORT=3456
+    API_URL="http://localhost:$API_PORT"
+
+    echo "Using test directory: $TEST_DIR"
+    echo "Using vault test directory: $VAULT_TEST_DIR"
+    echo "Using vault PID file: $VAULT_PID_FILE"
+
+    # Function to cleanup on exit
+    cleanup() {
+        echo "Cleaning up resources..."
+        if [ -n "$SERVER_PID" ]; then
+            echo "Stopping server process ($SERVER_PID)..."
+            kill -9 $SERVER_PID 2>/dev/null || true
+        fi
+        if [ -f "$VAULT_PID_FILE" ]; then
+            VAULT_PID=$(cat "$VAULT_PID_FILE")
+            echo "Stopping vault process ($VAULT_PID)..."
+            kill -9 $VAULT_PID 2>/dev/null || true
+        fi
+        # Clean up all temporary files and directories
+        rm -rf "$TEST_DIR"
+        rm -rf "$VAULT_TEST_DIR"
+        echo "Cleanup complete."
+    }
+
+    # Error handling function
+    handle_error() {
+        echo "Error encountered, exiting..."
+        cleanup
+        exit 1
+    }
+
+    # Set trap for errors and interrupts
+    trap handle_error ERR
+    trap cleanup EXIT
+
+    # Check if Vault is installed
+    if ! command -v vault &> /dev/null; then
+        echo "Vault is not installed in the test environment."
+        exit 1
+    fi
+
+    # Check if there's already a Vault process running with our PID file
+    if [ -f "$VAULT_PID_FILE" ]; then
+        VAULT_PID=$(cat "$VAULT_PID_FILE")
+        if ps -p $VAULT_PID > /dev/null; then
+            echo "Vault is already running with PID $VAULT_PID"
+            echo "Stopping the existing Vault server..."
+            kill -9 $VAULT_PID
+            rm "$VAULT_PID_FILE"
+            # Wait for the port to be released
+            sleep 2
+        else
+            echo "Vault PID file exists but the process is not running. Removing stale PID file."
+            rm "$VAULT_PID_FILE"
+        fi
+    fi
+
+    echo "Starting Vault server in non-dev mode..."
+
+    # Create temporary config file
+    mkdir -p "$VAULT_TEST_DIR/data" "$VAULT_TEST_DIR/config"
+
+    cat > "$VAULT_TEST_DIR/config/vault.hcl" << EOF
+    storage "file" {
+      path = "$VAULT_TEST_DIR/data"
+    }
+
+    listener "tcp" {
+      address     = "127.0.0.1:8200"
+      tls_disable = "true"
+    }
+
+    disable_mlock = true
+    ui = false
+    EOF
+
+    vault server -config="$VAULT_TEST_DIR/config/vault.hcl" > "$TEST_DIR/vault_server.log" 2>&1 &
+    VAULT_PID=$!
+    echo $VAULT_PID > "$VAULT_PID_FILE"
+
+    echo "Vault server started with PID $VAULT_PID"
+    echo "Vault server is running at $VAULT_ADDR"
+
+    # Wait for Vault to start
+    echo "Waiting for Vault to start..."
+    sleep 5
+
+    # Check if Vault is up and running
+    for i in {1..10}; do
+      if wget -q -O- --no-check-certificate http://127.0.0.1:8200/v1/sys/health?standbyok=true\\&sealedok=true\\&uninitok=true > /dev/null 2>&1; then
+        echo "Vault is up and running!"
+        break
+      fi
+
+      if [ $i -eq 10 ]; then
+        echo "Timed out waiting for Vault to become available"
+        exit 1
+      fi
+
+      echo "Vault is unavailable - sleeping (attempt $i/10)"
+      sleep 2
+    done
+
+    # Start the vault-hier server
+    echo "Starting the vault-hier server..."
+    echo "Using API port: $API_PORT"
+    ${vault-hier}/bin/vault-hier server --vault-addr "$VAULT_ADDR" --api-port $API_PORT > "$TEST_DIR/api_server.log" 2>&1 &
+    SERVER_PID=$!
+    echo "Server started with PID $SERVER_PID"
+
+    # Wait for the server to start
+    echo "Waiting for the server to start..."
+    sleep 10  # Increased wait time to ensure server is ready
+
+    # Test the server with some client operations
+    echo "Testing the client operations..."
+
+    # Create a sample file for testing
+    echo "Creating a sample file for testing..."
+    echo "This is a test document" > "$TEST_DIR/test_document.txt"
+
+    # Test login with legal1 user
+    echo "Testing login with legal1 user..."
+    LOGIN_OUTPUT=$(${vault-hier}/bin/vault-hier login --username legal1 --password legal1pass --api-url "$API_URL")
+    echo "$LOGIN_OUTPUT"
+
+    # Just check that login command executes successfully
+    echo "Login command executed successfully"
+
+    # Test basic commands (these should at least parse correctly)
+    echo "Testing help command..."
+    ${vault-hier}/bin/vault-hier --help
+    if [ $? -ne 0 ]; then
+      echo "ERROR: Failed to run help command"
+      exit 1
+    fi
+
+    # Test version command
+    echo "Testing version command..."
+    ${vault-hier}/bin/vault-hier --version
+    if [ $? -ne 0 ]; then
+      echo "ERROR: Failed to run version command"
+      exit 1
+    fi
+
+    echo "End-to-end tests passed successfully!"
+    exit 0
+  '';
+
+  # Create the derivation that will run the tests
+  e2eTests = pkgs.runCommand "vault-hier-e2e-tests" {
+    buildInputs = [
+      vault-hier
+      pkgs.vault
+      pkgs.wget
+    ];
+    nativeBuildInputs = [
+      pkgs.jq
+      pkgs.wget
+    ];
+  } ''
+    # Run the test script
+    ${e2eTestScript}/bin/run-e2e-tests
+
+    # Create a success marker file to indicate the tests passed
+    mkdir -p $out
+    touch $out/success
+  '';
+in
+e2eTests