diff --git a/CMakeLists.txt b/CMakeLists.txt
index d7971d9..f8c6d02 100644
--- a/CMakeLists.txt
+++ b/CMakeLists.txt
@@ -73,6 +73,7 @@ set(PRJ_LIBRARIES
     Boost::iostreams
     Boost::thread
     Boost::filesystem
+    Boost::outcome
     cryptopp::cryptopp
     ZLIB::ZLIB
     OpenSSL::SSL
@@ -86,7 +87,7 @@ find_package(fmt CONFIG REQUIRED)
 find_package(doctest CONFIG REQUIRED)
 find_package(spdlog CONFIG REQUIRED)
 find_package(httplib CONFIG REQUIRED)
-find_package(Boost REQUIRED COMPONENTS system iostreams thread filesystem)
+find_package(Boost REQUIRED COMPONENTS system iostreams thread filesystem outcome)
 find_package(cryptopp CONFIG REQUIRED)
 find_package(ZLIB REQUIRED)
 find_package(OpenSSL REQUIRED)
diff --git a/src/Identity.cpp b/src/Identity.cpp
index 480ac2d..88d7fb5 100644
--- a/src/Identity.cpp
+++ b/src/Identity.cpp
@@ -1,6 +1,7 @@
 #include "Identity.h"
 #include "Http.h"
 #include <filesystem>
+#include <fmt/core.h>
 #include <fstream>
 #include <nlohmann/json.hpp>
 #include <spdlog/spdlog.h>
@@ -113,3 +114,95 @@ std::string Identity::login(const std::string& fields) {
     d.erase("public_key");
     return d.dump();
 }
+
+Result<ident::Identity, std::string> ident::login_cached() noexcept {
+    std::string private_key;
+    try {
+        std::ifstream key_file(ident::KEYFILE);
+        if (key_file.is_open()) {
+            auto size = fs::file_size(ident::KEYFILE);
+            key_file.read(&private_key[0], static_cast<long>(size));
+            key_file.close();
+        }
+    } catch (const std::exception& e) {
+        return fmt::format("Failed to read cached key: {}", e.what());
+    }
+
+    std::string pk_json {};
+
+    try {
+        pk_json = nlohmann::json {
+            { "pk", private_key }
+        }.dump();
+    } catch (const std::exception& e) {
+        spdlog::error("Private key had invalid format, please log in again.");
+        return std::string("Invalid login saved, please log in again.");
+    }
+
+    return detail::login(pk_json);
+}
+
+bool ident::is_login_cached() noexcept {
+    return std::filesystem::exists(KEYFILE) && std::filesystem::is_regular_file(KEYFILE);
+}
+
+Result<ident::Identity, std::string> ident::login(const std::string& username_or_email, const std::string& password) {
+    std::string login_json {};
+
+    try {
+        login_json = nlohmann::json {
+            { "username", username_or_email },
+            { "password", password },
+        }
+                         .dump();
+    } catch (const std::exception& e) {
+        spdlog::error("Username or password has invalid format, please try again.");
+        return std::string("Username or password contain illegal characters, please try again.");
+    }
+
+    return detail::login(login_json);
+}
+
+void ident::detail::cache_key(const std::string& private_key) noexcept {
+    try {
+        std::ofstream key_file(ident::KEYFILE, std::ios::trunc);
+        key_file << private_key;
+    } catch (const std::exception& e) {
+        spdlog::warn("Failed to cache key - login will not be remembered: {}", e.what());
+    }
+}
+Result<ident::Identity, std::string> ident::detail::login(const std::string& json_params, bool remember) noexcept {
+    auto result = HTTP::Post("https://auth.beammp.com/userlogin", json_params);
+
+    nlohmann::json json = nlohmann::json::parse(result, nullptr, false);
+
+    if (result == "-1" || result.at(0) != '{' || json.is_discarded()) {
+        spdlog::error("auth.beammp.com failed to respond with valid user details");
+        spdlog::trace("auth.beammp.com/userlogin responded with: {}", result);
+        return std::string("Invalid answer from auth server. Please check your internet connection and see if you can reach https://beammp.com.");
+    }
+
+    try {
+        if (json["success"].get<bool>()) {
+            spdlog::info("{}", json["message"].get<std::string>());
+            ident::Identity id {
+                .PublicKey = json["public_key"].get<std::string>(),
+                .PrivateKey = json["private_key"].get<std::string>(),
+                .Role = json["role"].get<std::string>(),
+                .Username = json["username"].get<std::string>(),
+                .Message = json["message"].get<std::string>(),
+            };
+            if (remember) {
+                cache_key(id.PrivateKey);
+            }
+            return id;
+        } else {
+            spdlog::info("Auto-Authentication unsuccessful please re-login!");
+            return std::string("Failed to auto-login with saved details, please login again.");
+        }
+    } catch (const std::exception& e) {
+        spdlog::error("Incomplete or invalid answer from auth servers. Please try logging in again.");
+        spdlog::trace("auth.beammp.com/userlogin responded with incomplete data: {}", result);
+        return std::string("Failed to auto-login with saved details, because the auth server responded with invalid details.");
+    }
+}
diff --git a/src/Identity.h b/src/Identity.h
index fb7d92c..aed6e27 100644
--- a/src/Identity.h
+++ b/src/Identity.h
@@ -1,19 +1,34 @@
 #pragma once
-
+#include <filesystem>
 #include <string>
+#include "Result.h"
+
+namespace ident {
+
+constexpr const char* KEYFILE = "key";
+
 struct Identity {
-    Identity();
-
-    void check_local_key();
-
-    bool LoginAuth { false };
     std::string PublicKey {};
     std::string PrivateKey {};
     std::string Role {};
     std::string Username {};
-
-    std::string login(const std::string& fields);
-
-private:
-    void update_key(const char* newKey);
+    std::string Message {};
 };
+
+/// Whether a login is cached / remembered
+bool is_login_cached() noexcept;
+
+Result<Identity, std::string> login_cached() noexcept;
+
+Result<Identity, std::string> login(const std::string& username_or_email, const std::string& password);
+
+namespace detail {
+
+    Result<Identity, std::string> login(const std::string& json_params, bool remember) noexcept;
+
+    void cache_key(const std::string& private_key) noexcept;
+
+}
+
+}
+
diff --git a/vcpkg.json b/vcpkg.json
index 38dd166..f26b9f7 100644
--- a/vcpkg.json
+++ b/vcpkg.json
@@ -11,6 +11,7 @@
     "boost-iostreams",
     "boost-process",
     "boost-thread",
+    "boost-outcome",
     "nlohmann-json",
     "cryptopp",
     "zstd"